Boring History for Sleep - The Rise and Fall of the Pinkertons 🤠🔍 | America’s Most Infamous Detective Agency | Boring History For Sleep

Episode Date: July 15, 2026

Founded in the mid-nineteenth century, the Pinkerton National Detective Agency became one of the most powerful private law enforcement organizations in American history. From hunting outlaws and prote...cting railroads to infiltrating labor unions and guarding presidents, the Pinkertons operated in the shadows of some of the nation's biggest events.Admired by some and feared by others, the agency built a reputation that blurred the line between detective work, private security, and political influence. Its legacy remains one of the most controversial chapters in the history of crime and law enforcement.A calm journey through the Wild West, industrial America, famous investigations, and the extraordinary rise and decline of the Pinkertons.Boring History For Sleep — Soft stories about history's most fascinating institutions.

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Starting point is 00:00:00 Hey there, history hunters. Tonight we're cracking open the file on a name that once made bank robbers sweat. Presidents sleep easier, and factory workers reach for their pitchforks. The Pinkerton's. That eyeball and slogan outfit from old Western posters, the one you probably remember as the good guys chasing Jesse James across dusty plains. We'll buckle up because the real story is a lot stranger, a lot darker, and a whole lot more interesting than the cartoon version Hollywood sold you.
Starting point is 00:00:26 This is the tale of a Scottish runaway turned barrel maker turned spy, who built the first private detective empire in America, rode shotgun with Abraham Lincoln, basically invented the FBI before the FBI existed, and then watched his creation morph into the most hated private army of the industrial age. We're talking secret midnight train rides, undercover women who rewrote the rules of espionage, shootouts on riverboats,
Starting point is 00:00:50 and a single logo so iconic it literally gave us the phrase private eye. So before we get rolling, go ahead and smash that like button if you love a good Rise and Fall saga, and drop a comment telling me what city you're tuning in from and what time it is where you are. Seriously, I love seeing the map light up. Now dim those lights, get cosy, and let's step into the smoky gaslit world
Starting point is 00:01:10 of the never-sleeping eye. Ready? Let's roll. Our story begins, not in some dusty American saloon, or on a windswept prairie, but in the grimy industrial fog of Glasgow, Scotland, in the summer of 1819. The city was a soot-stained giant of cotton mills, and shipyards, a place where the working class lived stacked on top of each other in tenement
Starting point is 00:01:32 buildings that had all the charm of a damp sponge. Into this world was born a boy named Alan Pinkerton, the son of a police sergeant named William, who spent his days trying to keep order in a city that was rapidly losing it. William was the kind of father who came home smelling of gunpowder, street mud, and the particular brand of exhaustion that only comes from arguing with drunks for twelve hours straight. He was, by all accounts, a stern man, but a principal one, which in 19th century Glasgow was not exactly a recipe for a long and restful retirement. The family lived in the Gorbils, a neighbourhood that modern travel guides would politely describe as characterful and honest observers, would call something closer to terrifying. It was a warren of
Starting point is 00:02:14 narrow alleys and overcrowded lodgings, where the smell of cheap whiskey mingled with the smell of whatever else had been dumped in the street that morning. Alan was one of several children and his childhood unfolded against the backdrop of a city being violently reshaped by the industrial revolution. Factory owners were getting rich, factory workers were getting lung disease, and the gap between the two groups was widening by the hour. Young Alan learned to read, learned to fight, and learned very early on that the law, as practiced in Glasgow, did not always favour the people who needed it most. The turning point in the family's life, and arguably the turning point in the entire history we're about to unpack, came when Alan was just a small boy.
Starting point is 00:02:56 His father, William, still serving as a police sergeant, was sent out to help control a large public demonstration organised by a movement known as the Chartists. For the unfamiliar, the Chartists were a reform movement that had a genuinely radical demand for the time, which was that ordinary working men should be allowed to vote. In modern terms, this sounds about as controversial as asking for clean drinking water, but in the 1830s it was treated by the British establishment as something close to treason. Demonstrations were common, tempers were short, and the authorities had a habit of sending in men with batons to remind everyone who was really in charge. During one of these confrontations, William was struck in the head by a flying object,
Starting point is 00:03:37 and the injury was severe enough that he never fully recovered. He died not long after, leaving his wife and children in the kind of poverty that was common in Glasgow and depressing everywhere. With his father gone, the family slid into the kind of tight budget existence where every loaf of bread is a strategic decision. Alan was pulled out of school at around the age of 10, which was fairly standard in Glasgow at the time, though not exactly a glowing endorsement of the local education system. He was apprenticed to a Cooper, which is the old-fashioned word for a barrel maker. If the idea of spending your preteen years bending wooden staves over a fire sounds dull, that is because it mostly was, but coopering was a respected trade and a skilled
Starting point is 00:04:18 Cooper could find work almost anywhere in the industrial world, because almost everything, from whiskey to herring to gunpowder, was shipped in wooden barrels. Alan was quick with his hands, patient with detail, and he learned the trade thoroughly. Within a few years he had earned the rank of journeymen, which meant he could travel from town to town in search of better wages. During these teenage years, while he was hammering away at barrel hoops and sleeping in rented rooms, Alan started drifting into the same political waters that had swept his father under. He became involved with the Chartist movement himself, attending secret meetings, reading pamphlets that would have gotten him arrested in polite drawing rooms,
Starting point is 00:04:57 and befriending other young radicals who wanted to tear down what they saw as a rigged system. The cruel irony here is hard to miss. The same movement that had indirectly killed his father and now became his own political family. Whether he was doing this to honour William's memory, despite the system that had taken him, or simply because that is where his friends hung out after work is something historians still argue about. But the result was the same. By his early 20s, Alan Pinkerton was a known face in Chartist circles, a skilled tradesman with rough hands, sharp eyes, and a reputation for being slightly more willing to take risks than were strictly wise. It was during this period that he met a young singer named Joan Carfrey, a woman
Starting point is 00:05:38 with a steady voice and a steadier temperament, and the two were married in a quick and quiet ceremony in 1842. Joan would prove to be one of the most important figures in Alan's life, not because of any headline-grabbing adventures of her own, but because she had the almost impossible patience required to be married to a man who seemed magnetically drawn to trouble. She stood by him through everything that came next, and what came next arrived faster than either of them expected. Here is where the story gets murky, and here is where every honest biographer has to put up a small yellow flag of caution. Somewhere around this time, rumours began to circulate in chartist circles that Alan Pinkerton had been passing information to the authorities.
Starting point is 00:06:20 Whether this was true, partially true, or complete slander invented by jealous rivals is a question that cannot be answered with any certainty, because all the people who would have known for sure are long dead and left no clean paper trail behind. What is undeniable is that the rumors spread, Alan felt unsafe, and within weeks of his wedding he and Joan made the abrupt decision to flee Glasgow entirely. They packed a few belongings, boarded a ship bound for North America, and left Scotland behind forever. Whether they were running from the government, from former comrades, or from both at once, the ship did not particularly care. It just kept sailing west. The crossing was long, cramped, and unpleasant in the way that all transatlantic crossings of that era were unpleasant.
Starting point is 00:07:05 Passengers slept in stacked bunks, ate food of questionable origin, and listened to the groaning of the ship's timbers while trying not to think too hard about the depth of the water below them. The Pinkerton survived, which was not something every immigrant family could claim, and they eventually landed in the bustling port of Montreal, then made their way south to the United States. Alan was 23 years old, newly married, practically penniless, and carrying with him the twin burdens that would come to define the man he became. He had a deep respect for order and the rule of law, a legacy of his policeman father, and an equally deep instinct that the law sometimes had to be bent, or entirely bypassed if justice was going to be served. The young couple settled in a small Scottish immigrant community called Dundee, about 40 miles northwest of Chicago, tucked along the banks of the Fox River in Cain County, Illinois. The town was a modest cluster of wooden houses, a mill or two, and the kind of muddy main street where a good rain could swallow a wagon hole.
Starting point is 00:08:08 For Alan, though, it was a fresh start. He set up his own co-opridge, a small workshop where he made barrels for local farmers, brewers and merchants, and within a remarkably short time he was earning a decent living and building a reputation as a skilled craftsman. He was known to be honest, punctual, and almost aggressively hard-working, which is the kind of reputation that tended to stand out on the American frontier, where a fair number of craftsmen were more interested in the local whiskey than in their own workbenchers. But Alan was never just a barrel maker. Underneath the plain wood-shavings and the hammered iron hoops, he was still the political radical from Glasgow, still the young man
Starting point is 00:08:48 who believed that ordinary people had the right to fight rigged systems. And so, quietly, and without any fanfare, he turned the back of his copridge into a station on what was then called the Underground Railroad. For those who need a quick refresher, the Underground Railroad was not actually a railroad, which confused more than a few people at the time. It was a secret network of safe houses, guides, and sympathetic homeowners who helped enslaved people escape from the southern states to the free north, and often all the way to Canada. It was dangerous, illegal under federal law, and punishable by fines, prison time, or worse, depending on who caught you. Helping a single fugitive could ruin a man's business and his freedom, and Alan naturally helped
Starting point is 00:09:30 dozens. His workshop had a hidden compartment, a cellar area where escaped men, women and sometimes entire families could rest, eat, and wait for the next trustworthy guide who would take them further up the line. The neighbours either did not know or chose not to notice, which in immigrant communities was often the same thing in practical terms. Joan, for her part, cooked meals for strangers she would never see again, nurse sick children who passed through in the middle of the night, and kept the whole operation humming along without ever breathing a word about it to the curious folks in town. The Pinkerton's were not loud about their politics, which was smart, but because loud abolitionists in 1840s, Illinois, had a habit of ending up on the wrong end of a torch-wielding mob.
Starting point is 00:10:12 They simply did the work, one barrel and one fugitive at a time, and this, as it turned out, was a training program disguised as charity work. To run a station on the Underground Railroad, a person had to learn a very specific set of skills. First, you had to learn how to spot a spy. Slave catchers were professional and well-paid, and they often posed as sympathetic travellers in order to infiltrate the network and collect bounties. Second, you had to learn how to communicate without leaving evidence, which meant codes, signals, and a thousand tiny gestures that could carry meaning without ever being spoken out loud.
Starting point is 00:10:47 Third, you had to learn how to move people quietly through a hostile landscape which meant understanding roots, timing, and the habits of anyone who might be watching. And fourth, you had to learn how to trust other people's judgment about strangers, because the network only worked if each station could rely on the stations upstream and downstream. Without knowing it, Alan was teaching himself the exact skill set of an intelligence officer, decades before that term would exist in the form we know it. He was building mental maps of who could be trusted and who could not. He was learning how information travelled through human networks,
Starting point is 00:11:22 how secrets were kept and how secrets broke. He was learning that appearances were deeply unreliable, that a well-dressed stranger might be a bounty hunter and a ragged traveller might be a preacher with a hundred dollars sewn into his coat lining. All of this, in the backroom of a modest Scottish co-opridge on the edge of the American frontier, was quietly preparing him for a career he had not yet imagined.
Starting point is 00:11:45 And then, on a perfectly ordinary summer day in 1847, a career came looking for him. The story, as Alan told it himself and as it has been retold many times since, has the quality of an old campfire yarn, the kind of thing you half believe and half suspect of being polished up for the audience. But the general outline seems to be accurate enough.
Starting point is 00:12:06 Alan needed wood. Barrels, as it happens, require wood, and a cooper with a growing business needs a steady supply of the stuff. He had heard about a small, heavily wooded island sitting in the middle of the Fox River, an island that was not owned by anyone in particular, and that seemed to be free for the taking if you were willing to row out there and do the job.
Starting point is 00:12:25 chopping yourself. This was the sort of solution that appealed to a thrifty Scot with strong arms and his own rowboat. So on the appointed day Alan gathered his tools, pushed off from the riverbank and paddled out to the island alone. What he expected to find was peace, quiet, and a few decent oak trees. What he actually found was the remains of a campfire that had no business being there. The ashes were still warm, the ground was trampled in a way that suggested a group of several men had been spending time there recently, and a little further into the brush he spotted scraps of material that raised his eyebrows even higher. There were bits of melted metal, traces of soot on flat rocks, and the unmistakable smell of something that had been heated and hammered fairly recently.
Starting point is 00:13:10 This, as Alan's barrel-trained brain quickly calculated, was not exactly the camp of a couple of innocent fishermen. He rode back to the mainland without cutting a single tree because priorities had shifted. In 1847, the United States was in the middle of a serious problem with counterfeit money. The country did not yet have a single national currency the way it does today. Instead, different banks issued their own notes. There were dozens of designs floating around at any given time, and counterfeiters had absolute field days printing fake versions that could circulate for weeks before anyone noticed.
Starting point is 00:13:46 A good counterfeiting operation could do real damage to a local economy, and the island in the middle of the Fox River had all the... hallmarks of exactly that kind of operation, secluded, hard to access, easy to defend, and conveniently far from the nearest law enforcement officer with a badgner salary. Alan went straight to the sheriff of Kane County, explained what he had seen, and offered to help investigate. The sheriff, who probably had about two deputies and a pile of other problems on his desk, was delighted to let sharp-eyed immigrant Cooper do some of his work for him. Alan returned to the island, quietly and carefully, over the course of several days. He watched the patterns of activity, identified
Starting point is 00:14:26 who came and went, and eventually helped coordinate a raid that swept up the entire operation. The counterfeiters were arrested, their equipment was seized, and a surprising amount of fake currency was pulled out of circulation before it could cause further damage. Word got around. In a small community, a man who has quietly broken up a counterfeiting ring does not stay anonymous for long, and Alan soon found himself something of a local celebrity. A second counterfeiting case landed in his lap almost immediately, this one involving a larger and nastier gang, and he solved that one too. The pattern was clear. This Scottish Cooper had a gift for noticing things that other people missed, and even more importantly, he had the patience to act on those observations in a careful,
Starting point is 00:15:11 methodical way, rather than charging in like an angry bull. The county officials took notice. The county officials took notice, and in short order Alan Pinkerton was offered the position of Deputy Sheriff of Cain County. It was not a glamorous job. The pay was modest, the hours were unpredictable, and the work mostly involved tracking down horse thieves, settling fistfights, and trying to keep drunks from burning down their own houses. But for Alan, the badge represented something profound. For the first time in his life he had a legal official role in maintaining the law, a role that his father had held back in Glasgow and that had cost William his life. There was something almost poetic about the son of a Scottish police sergeant taking up the
Starting point is 00:15:52 same work on the Illinois frontier, though the poetry was probably lost on Alan at the time, given that he was usually too busy chasing cattle rustlers through the mud to appreciate it. More importantly, the deputy sheriff job revealed a truth that would shape the rest of Alan's career and, in a roundabout way, the rest of American law enforcement history. He discovered that the official forces of law in the United States were not remotely up to the scale of the country they were supposed to police. County sheriffs had limited budgets, limited manpower and almost no ability to operate outside their own county lines. If a criminal robbed a bank in Kane County and rode his horse into the next county over, the local sheriff often had to stop at the county border and wait for the neighbouring sheriff to pick up the chase,
Starting point is 00:16:37 which the neighbouring sheriff often declined to do because it was not his problem. and he had his own horse thieves to worry about. Criminals knew this, exploited it ruthlessly, and moved between jurisdictions the way modern tourists move between time zones. Alan, as a former chartist, with a keen eye for structural flaws,
Starting point is 00:16:57 saw this problem with painful clarity. The United States had a rapidly expanding economy, a booming population, an explosion of new railroads, and a patchwork of tiny local police forces that could not hope to keep up. There was a gap, a yawning chasm really, between what the country needed and what its official institutions could provide. And where there is a gap like that, someone eventually will step in to fill it.
Starting point is 00:17:23 Alan was beginning to suspect that the someone might be him. The cases piled up, his reputation grew, and he started receiving requests for help from further and further afield. Railroads in particular were becoming a major client because they had a very specific and very unsolvable problem. A train could cross half a dozen counties in a single afternoon, which meant that a single robbery might involve jurisdictions that barely spoke to each other and had no shared procedures for pursuit. The railroad companies did not want to wait for six different sheriffs to file six different reports. They wanted their property protected now. They wanted thieves caught yesterday, and they were willing to pay cold hard cash for the service. Alan understood what he was looking at.
Starting point is 00:18:07 This was not a small opportunity. This was an entire industry waiting to be invented, a market that the government could not serve and that private enterprise had not yet figured out how to enter. The Cooper from Glasgow, the barrel maker from Dundee, the deputy sheriff who could read a quiet campfire like other men read a newspaper, was about to make a decision that would create a whole new kind of American institution. He would turn private investigation into a profession, complete with its own rules, its own ethics, its own methods, and its own brand.
Starting point is 00:18:38 But before we get there, it is worth pausing for a moment to notice just how many threads were already woven together inside this one man. There was the memory of his father, dead on a Glasgow street for the crime of standing between demonstrators and a violent crowd. There was the radical young chartist, still alive somewhere underneath the respectable tradesman. There was the secret abolitionist, running a station on the underground railroad out of his own workshop. There was the deputy sheriff with a legal badge and a county salary, and there was the sharp-eyed observer who had single-handedly broken up two counterfeiting rings before he had even been a full-time lawman for a full year. Any one of those identities might have defined an ordinary life. Alan Pinkerton carried all of them at once, and the contradictions did not so much tear him apart as fuse him into something new. He was a man who genuinely believed in the rule of law. And at the same time, a man who had spent years, quietly breaking the laws he disagreed with. He was a man who distrusted powerful institutions
Starting point is 00:19:40 and at the same time a man who was about to build one of the most powerful private institutions the country had ever seen. He was a man who had fled political violence and at the same time a man whose creation would eventually be used decades later to unleash political violence on others. All of that was still ahead of him in 1847 as he stood on the banks of the Fox River with splinters on his hands and the beginnings of a much larger idea forming in the back of his mind. He did not yet know about the bank jobs he would solve, the spies he would unmask, the president he would protect, or the strikes he would one day be asked to break. He did not yet know that a single unblinking eye and a five-word slogan would become one of the most recognizable brands in
Starting point is 00:20:24 19th century America. He did not yet know that historians would still be arguing about him two centuries later. What he knew was this. He had a family to support, a workshop to run, a badge in his pocket, and a growing sense that the country he had adopted had bigger problems than any single sheriff could ever hope to solve. He was 30 years old, or close enough. He was strong, stubborn, literate, suspicious, principled, and slightly paranoid, which is a personality cocktail that does not often produce a happy retirement, but does tend to produce a very interesting career. By 1850, Alan had reached the point where something had to give. He could no longer pretend to be a Cooper who occasionally helped the sheriff. He was a detective who occasionally
Starting point is 00:21:11 remembered he owned a co-opridge, and his wife had probably stopped pretending to believe otherwise. The railroads were writing him letters asking for help, the banks were asking for help, the express companies were asking for help, and Chicago, 30-odd miles down the muddy road from Dundee, was rapidly becoming the beating commercial heart of the American Midwest. It was the kind of city where cattle, wheat, and money all passed through in enormous quantities, which meant it was also the kind of city where a person with a talent for catching thieves could find steady work for the rest of his life. Alan packed up his family and moved into the city and almost immediately went looking for a partner. He was a shrewd investigator, but he knew his limits. He had never been to law
Starting point is 00:21:54 school, he had only a rough grasp of the contracts and liability questions that came with running a proper business, and his handwriting, by most accounts, looked like a small bird had walked across the page with ink on its feet. What he needed was someone respectable, someone educated, and someone who could translate Alan's instincts into the kind of paperwork that Chicago's merchants would actually sign. He found exactly that in a local attorney named Edward Rucker, a man with an office, a reputation, and the ability to draft a contract that would hold up in court. The two of them founded the Northwestern Police Agency in 1850, a name that was chosen, one suspects, to sound as boring and official as possible. In the business of private investigation,
Starting point is 00:22:39 boring and official was a selling point. A potential client did not want a flashy agency with an exciting name. They wanted something that sounded like a solid institution, something that sat quietly in the background and got the job done. The partnership with Rucker was short-lived, lasting only about a year before the attorney decided that his legal career was a better bet than the unpredictable world of chasing train robbers.
Starting point is 00:23:03 Alan bought him out, rebranded the whole operation under his own name, and thus was born Pinkerton's National Detective Agency, the outfit that would eventually become the most famous private police force in the history of the English-speaking world. The moment Alan took full control, he started doing something that nobody else in the business had really bothered to do.
Starting point is 00:23:23 He wrote down the rules, he put them on paper, he drilled them into the men he hired, and then, because he was a former Cooper with a particularly Scottish view of human weakness, he enforced them with an iron grip. This code of conduct is probably the single most important thing that separated Pinkerton's agency from the hundreds of shady private detectives who were already roaming the country, most of whom were barely distinguishable from the criminals they claimed to pursue.
Starting point is 00:23:49 Rule number one was the rule about money. Most private investigators of the era worked on a bounty system. If you caught the thief, you got paid. If you did not catch the thief, you got nothing. This sounds perfectly reasonable until you think about it for more than ten seconds. A man who only gets paid for catching thieves has a powerful incentive to produce a thief, whether or not an actual thief exists. Innocent travellers could find themselves suddenly accused of crimes they had not committed
Starting point is 00:24:15 because some hungry investigator needed to eat that week. Evidence could be invented, witnesses could be bribed, and the whole profession had a well-earned reputation for being about as trustworthy as a $3 bill. Alan looked at this arrangement and decided it was rotten from the roots. He ordered that his agents be paid by the day. A flat rate for their time, regardless of whether the case ended in an arrest, a confession or a polite apology to the client for finding nothing at all. This small accounting change was, in its own quiet way, revolutionary.
Starting point is 00:24:48 It meant a Pinkerton agent had no financial reason to frame anybody, no reason to stretch a story, no reason to lean on an innocent man until he confessed to something just to make the pressure stop. The agent got paid for his hours and his effort, not for his results, which meant the results were, in theory, at least, honest ones. Naturally, this also meant Alan's agency was more expensive than the competition, but he was banking on the fact that a serious client would pay a little extra for the peace of mind
Starting point is 00:25:16 of knowing the report they received was actually true. Rule number two concerned entrapment. Agents were forbidden from pushing a suspect into committing a crime just so they could catch him doing it. This might sound obvious, but at the time it was not. Plenty of detectives earned their bread by shoving drinks into a suspect's hand, suggesting a robbery, driving the getaway wagon, and then leaping out at the crucial moment to claim the arrest. Alan's view, shaped by his early life on the receiving end of a Scottish police force that did not always play fair, was that a real detective caught real criminals doing real crimes,
Starting point is 00:25:51 not theatrical productions staged for the paying customer. Agents who were caught inducing crimes rather than documenting them would be fired, and word would spread, and the offending agent would find himself blacklisted in every reputable agency in the country. Rule number three, and in many ways the most unusual, was the rule about character. Alan demanded that his agents be not just skilled, not just loyal, but boringly respectable. No heavy drinkers, no gamblers, no men with known debts that could be exploited by bribes, no hotheads with short tempers who might pull a pistol before they thought a situation through. He interviewed candidates personally, asked about their families, their politics, their religious habits,
Starting point is 00:26:32 their sleeping patterns, and in one famous instance, their handwriting, because Alan believed a man's handwriting revealed more about his soul than his mouth ever would. This last detail sounds like pseudoscience from a modern perspective, and to be fair it was, but it was the kind of earnest 19th century pseudoscience that at least pointed at the right question. Alan wanted to know who his men really were, not just what they could do. The men he hired were expected to keep journals, submit daily written reports, account for every hour of their time, and maintain a personal appearance that would not embarrass the agency. They were also required to adopt, on duty, the plain blue suit and derby hat that would eventually become the unofficial uniform of the Pinkerton operative. The idea was to look professional without looking like a policeman, to blend in without disappearing, and to project the quiet authority of a man who knew something the people around him,
Starting point is 00:27:28 did not. The agency needed its first big break, of course, and that came from a company called the Adams Express Company. For those unfamiliar with 19th century commerce, express companies were essentially the private shipping giants of their day, hired by banks, businesses and government offices to move cash, documents, and valuable packages across the country. Before there was a reliable postal service for money, there was Adams Express and a handful of competitors, trundling along in iron reinforced wagons and locked train cars filled with gold, silver, banknotes, and the occasional nervous accountant. The company's problem was obvious. Every shipment was a target, every route had vulnerable sections, and the country was full of ambitious men who had read about stagecoach
Starting point is 00:28:15 robberies, and decided they too would like to try that career path. Adams Express hired Pinkerton's agency on a retainer, which in business terms meant a steady ongoing monthly payment in exchange for continuous protection services. This was a far better arrangement for Alan than the occasional one-off case, because it gave him a predictable income that he could use to expand operations, hire more agents, and build the kind of infrastructure that would eventually set the agency apart. It was also, perhaps more importantly, a massive endorsement. If Adams Express trusted Pinkerton's to protect its shipments,
Starting point is 00:28:49 then other companies quickly decided they should too. Within a few years, the agency had contracts with half a dozen railroads, a handful of major banks and a growing list of smaller commercial clients who did not want to pay for full-time protection, but were happy to call Alan whenever something went wrong. It was during this period of expansion that the agency developed what would become perhaps the single most recognizable corporate image of 19th century America. Alan needed a logo, something that could go on business cards, on office windows, on stationary, and on the advertisements he was planning to run in local newspapers. He also needed a slogan that would stick in the mind of both his customers
Starting point is 00:29:28 and, more importantly, his targets. He wanted criminals to see his agency's image and feel the small cold sensation at the back of the neck that tells a person he is being watched. What he came up with was a single, large, wide-open human eye, drawn in stark black ink with no background, staring directly out of the page at whoever looked at it. The eye did not blink, The eye did not close. The eye, the advertisement said, never rested. Around or beneath this image, depending on the format, was the slogan that would outlive the man who invented it. We never sleep. Three short words printed in bold letters, carrying a double meaning that was genuinely clever. For the paying client, it meant that the agency was always on duty, always vigilant, always prepared to respond to a crisis.
Starting point is 00:30:17 For the criminal, it meant something closer to a warning. We are watching. We are awake when you think you are safe. You do not know when we are looking at you, but we are. The eye and the slogan had an effect that went far beyond simple advertising. They seeped into the language itself, which is a rare achievement for any piece of corporate branding. By the late 19th century, a private detective of any kind, whether employed by Pinkerton or not, was commonly called a private eye, a phrase that came directly from the famous logo.
Starting point is 00:30:49 Mystery writers picked up the term, Pulp novelists embraced it. Eventually, Hollywood built an entire genre of film around the idea of the trench-coated private eye wandering through rainy city streets looking for clues, and although the hard-boiled detectives of the 20th century bore very little resemblance to Alan's straight-laced blue-suited operatives, they owed their name, and in some ways their profession, to a logo invented by a Scottish Cooper in Chicago in the 1850s. The office in Chicago became the nerve centre of a rapidly growing operation. Agents were sent out on cases all over the country,
Starting point is 00:31:24 and they returned with stories, evidence, photographs, and increasingly suspicions. It was here, in the agency's modest headquarters, that Alan Pinkerton made the invention that is arguably his single most important contribution to modern law enforcement, and the one that modern law enforcement has almost entirely forgotten to credit him for, which brings us to the matter of paperwork, and specifically to the fact that Alan Pinkerton may have been the first man in American history to realise that paperwork was a weapon.
Starting point is 00:31:55 Think for a moment about how a criminal operated in the middle of the 19th century. If a man robbed a store in Ohio, the local sheriff might know his face, might have a rough description, might even know his name. But the sheriff's knowledge was true. trapped inside the sheriff's own head and his own small filing drawer. If that same man rode a few hundred miles west and robbed another store in Missouri, the Missouri Sheriff had no way of knowing that the suspect was a repeat offender. There was no telephone for the two sheriffs to call each other on. There was no teleprinter. There was no federal database. There was not even a reliable
Starting point is 00:32:29 postal description system. A criminal could genuinely erase his past by simply buying a train ticket, and this was exactly what a lot of them did on a regular basis. Alan looked at this situation and reached a conclusion that should have been obvious but apparently was not. Information he decided ought to travel at least as fast as the criminal did. If a man robbed a store in Ohio and then showed up in Missouri six weeks later, the Missouri sheriff ought to be able to find out about his Ohio history. The problem was that no official institution was willing or able to build the system required to make that possible. So Alan built it himself.
Starting point is 00:33:06 He called it the Rokes Gallery, or sometimes just the criminal, archive, and it was housed in a set of filing cabinets in the Chicago office. Each file contained, where possible, a photograph of the suspect, a written physical description, a list of known aliases, a summary of past crimes, notes on the suspect's known associates, samples of his handwriting, and any other scrap of information that an agent had managed to collect. Photography was still a relatively new technology at the time, and a good clear photograph of a known criminal was a treasure. The agency went to considerable lengths to obtain them, sometimes by having agents poses travelling photographers,
Starting point is 00:33:43 sometimes by purchasing portraits from prison wardens, sometimes by quietly photographing suspects in public places without their knowledge. The files grew, and as they grew they became something new. They became a distributed memory, a shared brain that no individual person could carry. When a client hired Pinkerton's to investigate a crime, the agents in the field could send a description of the suspect back to Chicago. And within days they might receive a telegram saying, yes, we know this man.
Starting point is 00:34:14 Here is his real name. Here are his known hiding places. Here is who he drinks with. Here is the type of crime he prefers. It was, in the language of a later century, a database. In the language of the 1850s it was magic. Or, more accurately, it was systematic work done patiently over many years by hundreds of agents, which to an outside observer was in.
Starting point is 00:34:34 indistinguishable from magic. Alan marketed this capability aggressively in his advertising. A Pinkerton agent, the pitch went, knew more about the criminal on your train than the local sheriff ever would. A Pinkerton agent could identify a suspect by his handwriting, his walk, his associates, his tattoos, his scars, and the particular way he pronounced the name of his hometown. The competition, who mostly kept no records at all and relied on the patchy memory of individual detectives, could not come close. Within a remarkable, In a remarkably short time, the agency had built a near monopoly on the idea of systematic criminal intelligence in the United States, and they guarded that monopoly jealously.
Starting point is 00:35:13 The Rogue's Gallery grew to contain tens of thousands of records. Photographs were cross-indexed by physical features, so that an agent who knew only that a suspect had a scar on his left cheek, and spoke with a New Orleans accent, could narrow down the candidates in minutes rather than weeks. Handwriting samples were compared side-by-side in specially designed books. Descriptions were filed by crime type, by geographic region, and by criminal specialty. Pickpockets went in one drawer, safecrackers in another, counterfeiters in another, confidence artist in a fourth. It was the kind of tedious, obsessive, thankless work that nobody wanted to do, and Alan insisted on it relentlessly.
Starting point is 00:35:55 His agents grumbled about the paperwork, which was the universal response of law enforcement personnel to paperwork in every era of history, but they did it anyway because they understood that it was what made the agency actually work. There is a small and slightly ironic footnote to all of this, which is that the Pinkerton Archive eventually became so respected that law enforcement agencies from other countries began writing to Chicago to request information. European police forces, who considered themselves more sophisticated than their American counterparts, found themselves humbly asking a private American agency for files on criminals who had crossed the Atlantic. This was not the usual direction of 19th century intellectual exports,
Starting point is 00:36:36 and it surprised quite a few people on both sides of the ocean. A former barrel maker from Glasgow had somehow built an information system that the professional police of London, Paris and Berlin were quietly trying to imitate. Back in the 1850s, though, all of this was still decades away. Alan had his logo, his slogan, his Code of Conduct, his first major clients, and the beginnings of his famous archive. What he did not yet have was the one thing that were trying to, transform him from a successful regional businessman into a household name across the entire country.
Starting point is 00:37:08 He did not yet have a president, and he did not yet have a war. Both were coming, faster than he or anyone else suspected, and they would drag the unblinking eye of the Pinkerton Agency directly into the most dangerous years in American history. The filing cabinets in Chicago were getting fuller. The agents in their plain blue suits were spreading out along the railroad lines. The advertisements with the staring eye were appearing in newspapers from Boston to New Orleans. And in Springfield, Illinois, not far from Allen's Chicago office, a tall, awkward, melancholic lawyer named Abraham Lincoln was quietly preparing for a political career that would soon collide with Allens in ways neither man could have predicted.
Starting point is 00:37:48 But that is a story for the next chapter. For now, the eye simply watched. Visit BetMDM Casino and check out the newest exclusive, The price is right fortune pick. BetMDM and GameSense remind you to play responsibly. 19 plus to wager. Ontario only. Please play responsibly.
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Starting point is 00:38:40 moment it caught them. The summer of 1856 in Chicago was hot, humid and smelled the way any rapidly industrialising city on the edge of a freshwater lake tends to smell in August, which is to say not particularly pleasant. Alan Pinkerton was sitting in his office on Washington Street reviewing reports when a visitor arrived without an appointment. His secretary announced that a young woman was waiting in the outer room and wished to speak with him about a job. Alan, who was used to this sort of interruption, assumed she was applying for a clerical position. The agency was growing fast. The paperwork we have already discussed was piling up at an alarming rate, and there was always room for a careful young woman who could file documents without losing them.
Starting point is 00:39:22 He told the secretary to send her in. The woman who walked through the door was 23 years old, slim, dark-haired, and possessed of a gaze that Alan would later describe in his writings as surprisingly direct. Her name was Kate Warn. She was a recent widow, originally from New York State, and she had, as it turned out, read one of the agency's advertisements in a Chicago newspaper. The advertisement had mentioned the hiring of new agents. She was applying to be an agent, not a secretary, not a clerk, an operative, the kind who went out into the field, watched suspects, and submitted reports, that kind.
Starting point is 00:40:00 Alan, to his credit, did not immediately laugh her out of the office, which was the reaction most employers in 1856 would have had to the same situation. He did, however, try gently to explain that this was not a job open to women. He had hired his wife to help run the Underground Railroad Station years earlier, and he had employed a few women in minor supporting roles at the agency. But the idea of a woman as a full-field operative, paid to do the same work as his blue-suited men, was not something that had ever occurred.
Starting point is 00:40:27 to him. He told her, with what he hoped was courteous firmness, that the profession was simply not suitable. Kate Warn, by every account that has come down to us, then proceeded to change his mind in what seems to have been a remarkably short conversation. Her argument was the kind of argument that, in retrospect, sounds so obviously correct that you wonder how nobody had made it before. A woman, she explained, could go places no man could go. A woman could sit in a parlour with the wife of a suspect and learn more in one afternoon over tea than a male agent could learn in a month of shadowing him through saloons. A woman could befriend a female servant and get inside information about her employer's private life, his correspondence, his finances, his affairs. A woman could
Starting point is 00:41:12 travel alone on a train, or accompanied by a different male agent acting as her husband, without raising the slightest suspicion. Men, she said, tended to talk more freely in the presence of a woman they did not suspect, because they did not expect her to understand what they were saying, let alone to remember it and report it. This last point in particular seems to have landed squarely on Alan. He thought about his own cases. He thought about all the times his male agents had reached a dead end because they could not gain access to a domestic setting, could not talk to a wife or a mistress or a housekeeper, could not sit quietly in a corner of a boardinghouse parlour and listened to what the residents were saying when they thought nobody important was present.
Starting point is 00:41:53 He thought about the sheer scale of the blind spot that ran through his entire operation, a blind spot roughly the size of 50% of the adult population of the country. By the end of the interview, Kate Warn had a job. She was formally hired as a detective of the Pinkerton National Detective Agency, at a daily rate equal to that of her male colleagues, a detail that would have scandalised most American employers of the period if they had bothered to find out. She became, by the most reliable historical reckoning, the first professional female private detective in the United States, and very possibly the first
Starting point is 00:42:28 in the English-speaking world. Alan later wrote, with the earnest pride of a man who had convinced himself he had discovered something, that he had recognised her talents immediately. The diary evidence and correspondence suggest he had in fact needed some convincing. But Kate had been persuasive enough to do the convincing, which was itself a demonstration of the skill set he was hiring her for. Her early months at the agency were an experiment, and not an easy one. The male agents, as you might imagine, were not universally delighted to find themselves sharing an office with a woman who held the same title they did and was earning the same pay. Some were openly dismissive, others were quietly resentful. A few, however, recognized very quickly that Kate was
Starting point is 00:43:13 exceptionally good at the work, and they began to accept her as a colleague. Alan, for his part, deliberately assigned her to cases where her particular advantages would be impossible to ignore. He wanted results that would shut down any office grumbling before it could harden into real opposition. The first major case in which Kate demonstrated what a trained female operative could do involved the Adams Express Company, the client we have already met. A large sum of money, something on the order of $50,000 in cash, had vows. vanished from a locked pouch while in transit. The company suspected an inside job, specifically a young courier named Nathan Moroni, but suspicion was not proof,
Starting point is 00:43:52 and they could not fire him, let alone prosecute him, without evidence. Alan accepted the case, and designed what amounted to a long, patient psychological operation around the suspect and his wife. The wife, as it happened, was friendly, sociable, and spent a great deal of time in the parlors and tea rooms of Montgomery, Alabama, where the couple lived. A male agent could not realistically approach her. A female agent could. Kate was sent south under a false identity,
Starting point is 00:44:20 posing as a wealthy widow from a respectable family, and she took rooms at the same boarding house. Over the course of several weeks, she befriended Mrs. Marini, through the slow, patient work of shared meals, shared walks, shared confidences about the difficulties of being married to men in uncertain occupations.
Starting point is 00:44:38 Kate listened more than she spoke, which is the cardinal rule of undercover work, and also it happens, of making friends in general. The friendship deepened. Mrs. Marany, who had been carrying the secret of her husband's theft alone, and was near the breaking point of her nerves, eventually unburdened herself to the kind, attentive widow she had come to trust. Kate listened sympathetically, offered advice, and quietly reported every detail back to the agency. Other Pinkerton operatives, meanwhile, were working different angles, pressing on the husband through a separate ruse involving a jailhouse conversation with a planted agent posing as a fellow prisoner.
Starting point is 00:45:16 The combined pressure, applied from multiple sides simultaneously, eventually produced the result that the Adams Express Company had been paying for. The money was recovered, most of it, and Nathan Maroney was convicted. It was an enormous success, and it made Alan a great deal of money, and it firmly established in his mind that Kate Warn was not a novelty hire, but a genuine asset who was doing work that simply could not have been done without her. More importantly, he realised that she was not going to be the only one. If Kate could do this, others could too. Within a year or so, Alan formally established what he called the Female Detective Bureau of the Pinkerton National Detective Agency, and he placed Kate Warn in charge of it. This was another first, and another one
Starting point is 00:46:01 that the history books have not always given the attention it deserves. The Female Detective Bureau was, as far as anybody has ever been able to determine the first organised unit of professional female investigators anywhere in the United States. And Kate was its first director. She recruited, she trained, she assigned cases, she reviewed reports, and she answered to Alan directly
Starting point is 00:46:24 rather than to any of the male supervisors in the main office. Her agents range from young women fresh out of difficult circumstances to older widows with extensive social connections they were willing to put to creative use. Alan encouraged diversity of background because different cases required different types of cover and a bureau that contained only 23-year-old brunettes would have been useless when the situation called for, say,
Starting point is 00:46:48 a grey-haired matron with a Boston accent. The training Kate developed, though much of it has been lost to the archives or simply never written down, can be partly reconstructed from the reports her agents filed and from Alan's own later books. Her operatives were taught the state, standard Pinkerton skills of observation, memory and documentation. They were also taught a set of
Starting point is 00:47:09 skills that the male agents were not formally trained in, because the male agents, frankly, did not need them. Kate's women learned how to read a room of other women, how to detect the small signs of strain or deception in a domestic setting, how to manage a long false identity without slipping up in unguarded moments, how to extract information through sympathetic conversation rather than direct questioning and how to exit a situation gracefully when the assignment was complete without leaving a trail that could later be traced. They also learned to play a remarkable range of cover roles. Depending on the case, a Kate Warn operative might appear as a fortune teller, a travelling preacher's wife, a seamstress looking for work, a grieving widow seeking solace in a new
Starting point is 00:47:51 town, a lady's maid, a wealthy heiress, a schoolteacher, a nurse, or in at least one case, a professional mourner hired to attend a suspect's funeral and listen carefully to what the other mourners whispered to each other. The range of possibilities available to a well-trained female operative was, as Alan observed in his correspondence, dramatically wider than the range available to a male one, for the simple reason that nobody in 19th century America expected a woman to be a spy. The mere idea was, to most men of the period, vaguely ridiculous,
Starting point is 00:48:24 and this assumption was the single greatest tool the female detective bureau had. at its disposal. Kate herself continued to take on major assignments, even after she had moved into a supervisory role. She seems to have been constitutionally incapable of sitting behind a desk while her agents did the interesting work. She worked undercover as a southern bell, as a northern abolitionist sympathiser, as a fortune teller at a resort hotel, and perhaps most famously, as the travelling companion of a tall, awkward, melancholic man travelling under a false name on a night train between Baltimore and Washington in February of 1861.
Starting point is 00:49:01 We will get to that case in detail in the next chapter, because it deserves its own space and involves more moving parts than a single paragraph can hold. For now, it is enough to know that when the agency received the most politically sensitive assignment of the entire 19th century, Alan did not send a team of his seasoned male agents. he sent Kate. The women who worked under her care developed a kind of quiet legend within the agency. Male operatives who had started out skeptical came to regard them with a respect that
Starting point is 00:49:29 occasionally edged into awe. A male agent could shadow a suspect for weeks and still know less about him than a female agent who had spent one afternoon drinking tea with the suspect's mother. The agency files from this period, when they have survived, are full of reports written in careful hands, documenting conversations that no male investigator could have overheard, noting small domestic details that turned out to be the keys to otherwise impossible cases. There is something almost comical, in a quiet way, about the fact that a country which refused to let women vote, own property independently, or attend most universities,
Starting point is 00:50:07 was nonetheless, in this one obscure professional corner, employing them as some of its most effective intelligence operatives. The contradictions of the age did not always announce themselves, loudly. Sometimes they simply sat in a parlour and took notes. It is worth pausing on the matter of the personal cost involved in this work, because it was considerable, and the historical record does not always acknowledge it. Undercover operations of the sort Kate Ran were not glamorous. They involved long months away from home, in unfamiliar cities, maintaining false identities with no colleague to drop the mask with. An operative might live in a boardinghouse for six months under an invented name,
Starting point is 00:50:45 might befriend people she genuinely came to like, and might then disappear from their lives overnight when the case closed, knowing she could never contact them again. The emotional toll of this kind of work is difficult to measure but easy to imagine. Several of Kate's agents left the Bureau after a few years, citing exhaustion of a sort that did not have a name yet but that modern readers would recognise instantly as burnout. A few left because they had gotten married to men who did not want their wives doing such work,
Starting point is 00:51:14 which was the standard pattern of the era. A few simply could not handle the strain of living multiple lives simultaneously. Kate herself never married again, as far as the record shows. She lived in a series of boarding houses and rented rooms in Chicago, close enough to the office to walk to work, and she spent most of her waking hours either on assignment or training others. Alan, who was not generally given to sentiment, wrote about her in terms that come as close to admiration as he ever allowed himself in print. He called her indispensable, which in the mouth of a man as practical as Alan was the highest possible compliment. The relationship between Kate Warn and Alan Pinkerton has been the subject of some speculation among historians, in part because they were unusually
Starting point is 00:51:58 close professionally for a man and a woman of their time and station, and in part because Alan wrote about her with a warmth that some readers have found suggestive. There is no clear evidence that the relationship was ever anything other than an extremely strong professional partnership, and both of them were working long hours in a shared office during an era when gossip about such matters would have ended both their careers instantly. What seems clear is that Alan trusted Kate completely, that Kate trusted Alan in return, and that the two of them together built something that neither of them could have built alone. Whether there was anything beyond that, the letters and diaries have not told us, and the people involved took their answers with them.
Starting point is 00:52:37 The Female Detective Bureau continued to operate throughout the Civil War years, though its work during that conflict was largely folded into Allen's broader intelligence activities for the Union government. After the war, the Bureau continued under Kate's leadership, working on commercial cases, insurance fraud, domestic investigations, and the full range of work that the main agency handled. It was during this post-war period that some of the Bureau's most sophisticated long-term operations were developed, including several cases where female agents maintained cover identities for years at a stretch in order to gather evidence in complicated fraud investigations.
Starting point is 00:53:15 Kate Warn's life unfortunately ended far earlier than anyone expected. In January of 1868, at the age of just 35, she fell seriously ill with what the doctors of the day described as congestion of the lungs, which was a catch-all term that could mean almost anything from pneumonia to tuberculosis to a severe case of influenza complicated by the exhausting lifestyle of a field operative. Alan sat at her bedside in her final days
Starting point is 00:53:41 and when she died he arranged for her burial in the Pinkerton family plot in Graceland Cemetery in Chicago. This was an extraordinary gesture in its own way. Graceland was where Alan himself would eventually be buried and where his wife Joan would be buried and where his sons would be buried. To reserve a space in that plot for a female employee who was not a relative was a set.
Starting point is 00:54:02 statement about her importance to him and about her importance to the agency. That did not require further explanation. Her death left a genuine whole in the organisation. Other women followed in her role as head of the female detective bureau, and the bureau itself continued to operate for many years. But Kate had been the first, and she had been the one who proved the concept, and she had been the one who trained the first generation of American female operatives. Her agents carried her methods into cases across the country, for decades after her death, and some of them went on to train their own successes in turn. There is a direct professional lineage from Kate Warn to the female agents of the Bureau of
Starting point is 00:54:44 Investigation in the early 20th century, and from there to the modern day, though the intervening decades did not always remember the source of their own traditions. The consequences of Kate Warn's career extended well beyond the Pinkerton Agency itself. By the late 19th century, other detective agencies had begun hiring female operatives, partly because they had seen what Pinkerton's could do with them, and partly because their own clients had begun requesting such services. Novels and popular magazines started featuring female detective characters, drawing openly on the legend of the Pinkerton women, and the figure of the lady detective became a recognisable type in popular culture. By the time the character of the female private investigator reached Hollywood and the pulp fiction shelves of the 20th century,
Starting point is 00:55:27 The idea had become so familiar that audiences forgot it had ever been invented at all. But it had been. It had been invented in a specific place, in a specific decade, by a specific young widow who walked into a Chicago office in 1856 and refused to accept that the job was not available to her. What the Pinkerton Agency had discovered, quite by accident and very early in its history, was that the most powerful advantage an operative could have was invisibility,
Starting point is 00:55:55 and that there were entire categories of human beings. beings that society rendered automatically invisible in most social settings. Women were one such category. Children were another, though the agency was understandably reluctant to make systematic use of that one. Servants were a third, which is why so many Pinkerton operations involved agents posing as housekeepers, cooks, coachman and footmen. The people that the respectable classes did not look at, did not listen to, and did not suspect were the people the agency could turn into perfect eyes and ears. a kind of exploitation of social prejudice, turning the dismissiveness of the powerful into a weapon that could be used against them. This was, perhaps, the deepest insight that Kate Warren and her
Starting point is 00:56:37 bureau added to the developing art of modern investigation, and it is an insight that intelligence services around the world have been quietly using ever since. Which brings us naturally to that night train, and to the most politically charged assignment the Pinkerton Agency had ever accepted, and to the question of whether the long, lanky lawyer from Illinois would reach Washington alive or whether his presidency would end before it began in a railway tunnel in Maryland. Kate Warn was about to take on the most famous case of her career, and Alan was about to discover that the private detective business, which had so far dealt with fraudsters, forgers, and express company thieves, was about to step into something very much larger and far more dangerous than
Starting point is 00:57:19 anything the agency had handled before. The assignment that dragged the Pinkerton agency into national politics did not arrive in the form of a grand presidential request sealed with an eagle and a red ribbon. It arrived, fittingly enough, as an ordinary commercial contract with a railroad company. In the winter of 1860 to 1861, a man named Samuel Felton, who served as president of the Philadelphia-Wilmington and Baltimore Railroad, contacted Alan with a problem that sounded at first like the sort of thing the agency handled every week. Felton was hearing rumors that his railways line, which happened to pass through the increasingly hostile slave state of Maryland, might be the target of sabotage. Someone was whispering about plans to burn bridges, destroy ferry boats, and
Starting point is 00:58:07 cripple the route that connected the northern states to the nation's capital in Washington. This was, on the face of it, a fairly standard industrial security concern. Allen had handled plenty of sabotage threats before. What made the contract different was the political temperature of the country, at the moment Felton signed it. Seven southern states had already seceded from the Union in the weeks following the election of Abraham Lincoln in November. The nation was unraveling, slowly and then quickly, and the route between the North and Washington ran through a city, Baltimore, whose sympathies were very clearly tilted toward the southern cause. Keeping that railroad intact was not just a matter of protecting Samuel Felton's business
Starting point is 00:58:47 interests. It was a matter of whether the new president could physically reach the capital to take his oath of office. Alan accepted the job and immediately started deploying agents into Maryland. He went personally, operating under an assumed name, renting an office and setting himself up as a respectable businessman with apparent southern sympathies. He sent other male operatives to pose as sympathetic travellers, potential investors, and chatty railway passengers who could draw out the confidences of strangers in hotel lobbies and bar rooms, and he sent Kate Warn, who we have already met, into the drawing rooms and social circles where the genteel wives of Baltimore's secessionist leaders spent their afternoons. Kate operated under the assumed name of Mrs. Cherry,
Starting point is 00:59:31 presenting herself as a widow from Alabama who had travelled north to attend to some family business and had strong southern loyalties she did not bother to hide. This was exactly the kind of cover that 19th century Baltimore Society recognized and accepted with the question. A well-dressed southern widow with a soft accent and a tragic air was welcomed into tea parties, church socials and private dinners, and she was invited to listen to conversations that would have been instantly silenced if a strange man had been present in the same room. Her reports, delivered in careful code back to Alan's office, began to paint a picture that was considerably more alarming than a simple plan to burn a few bridges.
Starting point is 01:00:09 What Alan and Kate pieced together over the course of several weeks of fragmented evidence was this. A group of men in Baltimore, some of them prominent in local society and others drawn from the rougher precincts of the waterfront, appeared to be discussing a scheme to assassinate the president-elect during his planned stop in the city. Lincoln's route from Illinois to Washington for his inauguration had been publicized in detail because such trips were traditionally public events full of speeches, receptions and parade stop. The President-elect was scheduled to arrive at Baltimore's Calvert Street Station, travel by carriage across the city through an unprotected gap of about a mile to the Camden Street Station, and then board a different train to complete the journey to Washington.
Starting point is 01:00:53 That gap through the streets of Baltimore where Lincoln would be exposed in an open carriage, in a city full of people who hated him, was the pinch point around which the alleged conspiracy organized itself. The details Alan collected, or believed he had collected, suggested that a small group of men, planned to create a disturbance in the crowd, as Lincoln's carriage passed, used the chaos as cover, and shoot or stab the President-elect in the confusion. Alan referred to this as the Baltimore plot, and he treated it with the seriousness of a man who had just discovered a bomb under his own dining table. He sent word to Lincoln's travelling party through a chain of intermediaries that the
Starting point is 01:01:31 President-elect's life was in danger and that the planned schedule needed to be changed immediately. The reaction, as you might expect, was not instant belief. Lincoln was travelling with an entourage of political advisors, personal friends, and a handful of military officers assigned to his protection, and this entourage did not include any representatives of the Pinkerton Agency as part of its official security detail. From their perspective, a private detective from Chicago had just sent them a hysterical warning that the entire schedule of a presidential inauguration trip needed to be scrapped based
Starting point is 01:02:06 on rumours overheard at Baltimore Tea Parties, they were unsurprisingly somewhat resistant. Alan arranged an urgent meeting with Lincoln himself in a hotel room in Philadelphia, late in the evening of February 21, 1861. Several of Lincoln's close associates were present, including his law partner turned political lieutenant Norman Judd, and the atmosphere in the room was tense. Alan presented his evidence, which consisted largely of statements from his agents about what they had overheard in Baltimore. He argued that the only prudent course of action was to take Lincoln through Baltimore in secret, at a time nobody expected, by a route nobody anticipated. Lincoln, who had endured a truly exhausting journey through dozens of cities and had not planned
Starting point is 01:02:50 to sneak anywhere, was reluctant. He had a reception scheduled in Harrisburg the next day. He had speeches to make. He did not relish the idea of arriving in the capital of the Republic he was about to lead like a fugitive slipping into town under a false name. A second piece of evidence arrived that same evening independently through a completely different channel. William Seward, the incoming Secretary of State, had sent his son Frederick to find Lincoln with an urgent warning. Seward had been informed, through his own sources in Washington,
Starting point is 01:03:22 of a plot to assassinate the president-elect in Baltimore. The warning had come originally from General Winfield Scott, the aging but still highly respected commanding general of the United States Army, who had received his own intelligence from sources independent of the Pinkerton Agency. Two completely separate investigations conducted by people who did not know each other and did not share notes had arrived at the same conclusion. This, more than Alan's own arguments, seems to have tipped Lincoln's decision. If two different sets of investigators were warning him about the same city, something probably was going on in that city, Lincoln agreed.
Starting point is 01:03:58 agreed to alter his plans, though he insisted on going ahead with the scheduled events in Harrisburg the following day to avoid raising public suspicion. The revised plan was elaborate and required careful coordination. After the Harrisburg reception, Lincoln would slip out of his hotel in the early evening, take a special unmarked train back to Philadelphia, and from there catch the regular overnight train to Washington, arriving in Baltimore in the middle of the night hours earlier than anyone expected him to be in the city. The passenger manifests would show nothing unusual. the carriages would be switched between stations by the standard overnight procedure. The president-elect would, in theory, pass through Baltimore while most of the city was asleep, including, ideally,
Starting point is 01:04:40 the conspirators. Kate Warn was placed in charge of the sleeping car arrangements. She booked the last berth in the rear sleeping car under her assumed name, and reserved the adjacent births for herself and her supposed invalid brother, who was to be kept behind drawn curtains due to his fragile health. The invalid brother, of course, was Lincoln. Alan travelled in the same car, posing as another passenger. A third Pinkerton agent, a young man named George Bangs, handled liaison with the railroad staff to make sure the telegraph lines along the route were quietly disabled for the duration of the journey, so that no sympathetic operator could wire ahead to warn anyone that the special passenger was aboard. Lincoln, who was considerably taller than the average
Starting point is 01:05:22 sleeping birth was built to accommodate, spent the journey folded uncomfortably behind the curtains, wearing a soft travelling cap instead of his famous stovepipe, and with a shawl draped over his shoulders to disguise his very recognisable silhouette. Kate sat outside the curtain, attending to her supposed ailing relative and turning away any passengers who came too close with the gentle firmness of a professional nurse. The train rolled through the darkness toward Baltimore, passing small towns where secessionist flags had been raised in windows, and at some point in the early hours of February 23rd it reached the outskirts of the city itself. Baltimore's central train station required the passenger cars to be uncoupled from the locomotive
Starting point is 01:06:02 and pulled by horse team through the streets of the city to the other station, where they were then reconnected to a different engine for the onward journey to Washington. This was the standard procedure, and it was the very gap that had worried Samuel Felton and Alan and everyone else, because it meant that for about an hour in the middle of the night, the President-elect of the United States was sitting in a passenger car being pulled through the streets of a hostile city by horses, with no meaningful escort and no way to defend himself beyond the small pistols in the pockets of three private detectives.
Starting point is 01:06:33 Nothing happened. Whether this was because the conspirators, if they existed, had not expected Lincoln to pass through at that hour, or because the entire plot had never really been more than Tavern talk in the first place, or because the operation was simply so well concealed that no one had time to organise a response. It is a question that has been debated by historians ever since. What is not debated is that Lincoln emerged from the sleeping car in Washington shortly after six in the morning, met at the station by a handful of trusted associates and was taken quietly to his hotel.
Starting point is 01:07:04 He reached the capital alive. The inauguration went ahead as planned on March 4th. The Republic continued to exist, at least technically, though it was about to endure the most violent test of its existence that it had ever faced. The political aftermath of the Baltimore journey was awkward. When word got out that Lincoln had snuck into the capital under cover of darkness, the press had a field day. Cartoonists drew images of the new president skulking in a Scottish cap and a long military cloak, though in fact he had worn neither of these items. Southern newspapers mocked him as a coward. Northern papers ran embarrassed editorials wondering whether the country
Starting point is 01:07:42 had just elected a man who lacked the nerve to travel in his own country without hiding. Lincoln himself is said to have regretted the decision afterward, not because he doubted the warnings, but because the public reaction had damaged his image in ways that proved hard to undo. He told friends in later years that he should have gone through Baltimore openly, whatever the risk. Alan, for his part, believed he had personally saved the life of the 16th president of the United States, and he was not shy about saying so in every memoir, public statement and interview
Starting point is 01:08:11 he gave for the rest of his life. This claim did not go unchallenged. Wardhill Lehman, a Burley, Illinois lawyer and long-time Lincoln friend who had traveled with the inaugural party and served as one of Lincoln's unofficial bodyguards during the war, spent his own later years loudly disputing the entire story. Lehman wrote that there had never been a real plot at all, that Alan had inflated scattered tavern gossip into a dramatic threat in order to raise his own profile and win government contracts, and that the whole episode had been an embarrassing detour manufactured by an ambitious Chicago detective
Starting point is 01:08:44 looking to ingratiate himself with a new administration. The truth, as usually happens with these things, is probably somewhere in between the Allen version and the layman version, though how far along the spectrum is a question that historians are still cheerfully arguing about. Some version of a plot does seem to have existed, given that two independent investigations reached similar conclusions, whether it was a serious coordinated, well-financed effort or a loose collection of drunk secessionists running their mouths in barrooms is harder to say. What is clear is that Alan made the most of the incident,
Starting point is 01:09:19 that his profile did rise considerably in Republican political circles as a result, and that when the war broke out six weeks later and the new administration needed somebody at trusted to run intelligence operations for the army, Alan was at or near the top of the list. He accepted the assignment and immediately set about reinventing himself, or at least his identity for the new work. Operating an agency whose name was plastered on half the express wagons and bank windows in the country was useful for civilian investigations.
Starting point is 01:09:48 It was absolutely catastrophic for military intelligence work, because everybody in the country knew exactly who the Pinkerton's were and what they did. Any Southern sympathiser who saw Alan Pinkerton approaching would instantly know that a spy was in the room, so Alan adopted a wartime alias, taking the name Major E.J. Alan, and he would spend the next several years signing reports, contracts and memos under that name rather than his own. The alias was, it must be said, not particularly well concealed from anyone who cared to look. Plenty of people knew that Major Allen was in fact the owner of the Pinkerton Agency, but the fiction was maintained for official purposes and had allowed Alan to operate with a
Starting point is 01:10:27 degree of plausible deniability that his famous name would otherwise have ruled out. He was attached to the staff of General George B. McClellan, a young, handsome, meticulous officer who had been given command of the main Union Army in the Eastern Theatre of the War. McClellan and Alan knew each other from before the war, when McClellan had briefly worked as a railroad executive and had hired the Pinkerton Agency for various commercial matters. Their professional chemistry was, by most accounts, excellent. Their strategic judgment was, by most accounts less excellent, and this is where the story of Alan's military intelligence work gets complicated. The fundamental problem of running intelligence for the Union Army in the first half of
Starting point is 01:11:08 the Civil War was that nobody had ever done it before. There was no American military intelligence tradition, no established procedures for counting enemy forces, no standard methods for interrogating prisoners or analysing captured documents. Alan was essentially inventing the job as he went along, using the techniques he had developed in the private sector. He sent agents across the Confederate lines in civilian clothes to count regiments, estimate troop strengths and sketch fortifications. He interrogated runaway slaves who had escaped to Union lines, a population that often had detailed knowledge of southern military movements
Starting point is 01:11:43 because they had been working in and around the camps and forts in question. He gathered reports from Union sympathizers in the South, deserters from the Confederate Army, and captured enemy officers. The problem was that his methods, which worked beautifully for counting counterfeiters or tracking train robbers, did not scale well to the much larger and much more abstract question of how many men General Robert E. Lee actually had under his command on any given day. Alan tended to take every report at face value and add them altogether, which produced wildly inflated estimates of Confederate troop strength. McClellan, who was already temperamentally cautious and preferred not to attack until every possible advance,
Starting point is 01:12:25 was on his side, seized on Alan's numbers to justify staying put for weeks at a time while the Confederate Army moved around him. The result was a partnership that produced remarkably little military progress, but a great deal of paperwork, some of which suggested that the Union was facing a Southern Army roughly twice the size of the one that actually existed. Historians have been reasonably hard on Alan for this, though in his defence nobody else was doing any better at the same task in the same year. Military intelligence as a disson discipline was still in its infancy, and the tools he had available were not really equal to the problem he was being asked to solve. The agency he had built was designed to catch individual
Starting point is 01:13:04 criminals, not to estimate the size of entire armies, that the results were mixed was not exactly shocking under the circumstances. What Alan and his agents did accomplish, though, was a remarkable series of counterintelligence operations in and around Washington itself. The capital in the first year of the war was a leaky, rumour-soaked swamp of secessionist sympathisers, foreign spies and chattering socialites, many of whom had political or personal access to the highest levels of the Union government. Alan's agents were tasked with identifying these figures, documenting their activities, and, where appropriate, arresting them. This work produced a long list of uncomfortable results for the Washington Social elite, as person after person whom the city had considered a respected member of polite society
Starting point is 01:13:51 was revealed to be passing information south. The most famous case of this kind was a widow named Rose O'Neill Greenhow, a Washington socialite of considerable charm and even more considerable political connections. Rose moved comfortably in the highest circles of the capital, counting senators, cabinet officials and foreign diplomats among her regular dinner guests. She also happened to be a committed Confederate sympathiser, and she'd been running what a mounted to a small but effective spy ring from her elegant house on 16th Street, collecting information from her admirers and forwarding it south via a network of couriers. Alan's agents placed her under surveillance in the summer of 1861. They watched her house,
Starting point is 01:14:31 noted her visitors, documented her comings and goings, and intercepted some of her coded messages. The evidence they accumulated was overwhelming. In August of that year, Alan personally led the operation to arrest her, accompanied by several agents, and placed her under house arrest in her own home while the investigation continued. She was later transferred to a proper federal prison and eventually exchanged South in a prisoner deal, which allowed her to reach the Confederacy in triumph and write a rather self-satisfied memoir about her experiences.
Starting point is 01:15:02 The Greenhauer arrest was a public sensation, in part because it revealed just how deeply Confederate sympathizers had penetrated Washington society, and in part because Rose herself was a figure colorful enough to fill newspaper columns for weeks. It was also an early example of what would eventually become a major function of modern government intelligence services, namely, the investigation and arrest of domestic civilians suspected of passing information to an enemy power. Allen's agents wrote procedural manuals and reports on how they had conducted the operation,
Starting point is 01:15:34 and these documents would later be studied by the generations of federal investigators who followed. There is a fair question about whether everything Alan's agents did in this period was strictly legal, or even ethical by modern standards. Warrantless searches were the order of the day. Long-term surveillance of American citizens, including citizens who had not been charged with any crime, was carried out routinely. Arrests were sometimes made on the basis of very thin evidence, justified by the wartime emergency powers that Lincoln had assumed. Several of these activities would, in a later and more legally settled era, have produced serious constitutional objections. At the time, in the middle of a civil war with the capital itself under threat, the objections
Starting point is 01:16:16 that were raised were mostly brushed aside. Whether this was the right call or the wrong call depends very much on your view of emergency powers, executive authority, and the balance between security and liberty and wartime, which is a debate that has continued in American life ever since, and will probably continue for a long time yet. Alan's own view was straightforward. He believed that the Union was fighting for its survival, that Confederate sympathizers in the North were actively working to destroy it, and that any methods necessary to identify and neutralise those sympathizers, were justified under the circumstances. This was also, as it happened, the view of the Lincoln administration, which is why they kept paying him. The agency's bill to the
Starting point is 01:16:57 federal government during the war years ran into what was, at the time, serious money, though a reasonable chunk of it seems to have gone toward operational expenses that were never fully accounted for afterward. 19th century accounting practices and the confusion of a civil war combined to produce the kind of books that modern auditors would weep at. The partnership with McClellan ended when McClellan himself was removed from command in late 1862. Lincoln had lost patience with the general's endless hesitations and his persistent belief that he was outnumbered when he was not, and when the replacement general took over the Army of the Potomac, Alan lost his military rank and his official attachment to the army. He returned to running the agency full-time, with his reputation as a presidential confidant and intelligence pioneer,
Starting point is 01:17:42 firmly established, but his official government role now over. The war left a permanent mark on the American government. In July of 1865, just months after Lincoln was assassinated at Ford's Theatre, an event the Pinkerton's had no role in preventing, because they were no longer on the protection detail. The Department of the Treasury established a new bureau called the Secret Service. The melancholy irony is that the authorization was signed by Lincoln himself on the very afternoon he was shot,
Starting point is 01:18:11 and that the Secret Service's initial mandate was only to suppress counterfeiting, the very problem Alan had made his name fighting back in the 1840s. Presidential protection would not become its formal responsibility for decades, during which time two more American presidents were assassinated before the lesson was finally learned. Alan himself, now nearing 50, returned to Chicago, resumed direct control of the agency, and began focusing his attention on the new,
Starting point is 01:18:41 and rapidly expanding frontier of American crime. The war had created a generation of men who were comfortable with violence, familiar with firearms, and accustomed to taking what they wanted at gunpoint. Many of these men, once the fighting ended, did not return peacefully to civilian life. They drifted west, where the railroads were pushing further and further into sparsely populated territory, and where banks, express wagons and trains made tempting targets for groups of armed former soldiers with limited employment prospects. The age of the train robber was about to begin, which meant that the Pinkerton Agency,
Starting point is 01:19:18 having just spent several years chasing spies, was about to spend several decades chasing outlaws, and some of those outlaws were going to become legends in their own right. The agency that had protected a president-elect and arrested a society widow was about to meet the James brothers, the Reno gang, and a tall, quiet Texan named Butch Cassidy, and the story of how those encounters unfolded would, in many ways, change the public image of Alan's detectives forever. Before we follow Alan into the age of the train robbers and the dusty gunfights of the Western territories, we need to pause and look at a side of him that tends to get buried under the more colourful stories. Alan Pinkerton, the Scottish Cooper turned detective, was also one of the first
Starting point is 01:20:00 serious media strategists in American business history, and the agency he built survived and thrived not only because it caught criminals, but because it relentlessly, patiently, and with almost obsessive care shaped the story that the public heard about itself. This was an era before public relations existed as a formal profession. The term marketing, in the modern sense, had not yet been invented. And yet Alan, operating entirely on instinct, managed to build one of the most recognizable corporate brands of the 19th century, and then reinforce it through a deliberate and sustained campaign of self-published storytelling. The origins of this side of the business were practical rather than literary. By the end of the Civil War, the agency had handled hundreds of cases,
Starting point is 01:20:44 employed dozens of agents, and generated enough paper documentation to fill a small warehouse. Much of this material was, from a purely archival standpoint, dull beyond description. Daily reports, expense receipts, surveillance logs, transcripts of interrogations, coded telegrams between field offices, and more daily reports, because agents in the field were required to write one every 24 hours regardless of whether anything interesting had happened that day. The cabinets in Chicago groaned under the weight of it all, and Alan, sitting in his office in the late 1860s, began to think about what might be done with all that accumulated material
Starting point is 01:21:22 besides simply storing it. What he realized was that the raw case files contained the seeds of stories that the American reading public would pay good money to read. The country was in the middle of a publishing boom. Cheap printed books, which publishers called dime novels after their retail price, were being produced in enormous quantities and sold at railway stations, general stores and newsstands across the country. The subject matter tended toward adventure, violence, and exotic settings, and the appetite for new material was essentially bottomless. A man with access to the actual case files of the most famous detective agency in America had, in effect, a gold mine of potential stories sitting in his office filing cabinets. Alan started writing,
Starting point is 01:22:06 or at least started putting his name on the writing. There is a persistent debate about how much of the prose in the Pinkerton memoirs was actually written by Alan himself and how much was produced by ghostwriters working from his notes. The most plausible answer, based on the surviving evidence, is that Alan provided the raw material, the structural outlines, and the editorial supervision, while the actual sentences were crafted by professional writers he hired for the purpose. This was a perfectly standard arrangement in the publishing world of the time, and Alan was never particularly defensive about it. He was a detective and a businessman, not a literary stylist,
Starting point is 01:22:43 and he saw no point in pretending otherwise in private, even as his name appeared on the covers. The first of these books appeared in 1874 under the title The Expressman and the Detective, and it was a fictionalised account of the Nathan Marini case we have already encountered, the one in which Kate Warn had befriended the suspect's wife and extracted the evidence that led to conviction. Alan used real names in some places and invented names in others, reshaped the timeline for narrative effect, and generally produced a story that read more like a novel than a case file. The book sold well, better than well, actually. It sold in numbers that surprised both Alan and his publisher, and it made clear that there was a genuine commercial market for stories of this kind, written from the inside perspective of the detective rather than the outside perspective of the journalist.
Starting point is 01:23:29 Over the next decade and a half, Alan produced a steady stream of additional volumes, eventually reaching 16 books in total. The titles tell you most of what you need to know about the series. The Molly Maguire's and The Detectives, published in 1877, about a case we were. will cover in detail in a later chapter. The Spy of the Rebellion, published in 1883, which was his account of his wartime intelligence work, bank robbers and the detectives, 30 years a detective, the burglar's fate, and the detectives. The pattern is not subtle. Every book featured some combination of criminals and detectives, the detectives always won in the end, and the detectives, in almost every case, turned out to be employees of the Pinkerton National Detective Agency. Now,
Starting point is 01:24:16 This might sound like the most obvious, shameless corporate propaganda imaginable, and in one sense it absolutely was. The books were written, published, and distributed with the specific goal of making the agency look good and bringing in new clients. But what is genuinely interesting about them, and what separated them from the competing pulp detective fiction flooding the market at the same time, was the particular strategy Alan adopted for making his agents look good. He did not make them superhuman. This was not the approach that later generations of fictional detectives would take, where the hero has supernatural powers of observation, impossible physical abilities, and solutions that spring from his brain
Starting point is 01:24:56 as if by magic. Alan's detectives were portrayed as ordinary men and women with a specific and teachable skill set. They noticed small details. They kept careful notes. They worked in teams. They followed leads methodically. They interviewed witnesses patiently. They made mistakes, corrected them, and tried again. was a deliberate choice, and it was a brilliant one from a business perspective. A prospective client reading one of Alan's books was not looking for a hero, he was looking for a professional service. If the book made the detective sound like wizards, the reader would enjoy the story but would probably not expect any actual detective agency to be able to replicate
Starting point is 01:25:35 the results. By presenting his agents as disciplined, methodical professionals whose success came from technique rather than talent. Alan was communicating a specific and very marketable message, which was that the Pinkerton Agency delivered reliable results through repeatable methods. A bank president reading The Expressman and the Detective was not supposed to close the book and think, wow, what an amazing man that detective was. He was supposed to close the book and think, these people have a system, and the system works, and I can hire them to apply the same system to my problem. The books also served a second purpose, which was supposed to be a second purpose, which was a system. was to train the public imagination to accept the very idea of a private detective as a respectable
Starting point is 01:26:16 and trustworthy figure. This was not a given in the mid-19th century. Plenty of people regarded private investigators as shady, borderline criminal characters who were not really different from the crooks they claim to pursue. By publishing book after book in which Pinkerton agents were disciplined, honest, courageous, and successful, Alan was slowly reshaping the cultural category itself. The private detective was being a very important. redefined, one dime novel at a time, from a disreputable street figure into a recognisable type of professional. By the end of the 19th century, when actual literary authors started to take up the figure and write serious fiction about him, the groundwork had been thoroughly laid. The public was
Starting point is 01:26:59 ready for Sherlock Holmes, for Sam Spade, for every trench-coated investigator who would eventually follow, partly because Alan Pinkerton and his ghostwriters had spent 20 years convincing them that such a figure could exist in the first place, the influence on later fiction is surprisingly direct and has been traced by literary historians in some detail. Arthur Conan Doyle, writing in Scotland in the 1880s, was an enthusiastic reader of the Pinkerton memoirs. His own stories about a methodical, detail-oriented detective, working with a loyal companion and relying on systematic observation rather than instinct or violence, borrowed heavily from the model Alan had popularised. Conan Doyle actually set one of his most famous Sherlock Holmes novels, The Valley of Fear,
Starting point is 01:27:43 against the backdrop of an undercover Pinkerton operation based loosely on real events. The novel's undercover detective protagonist is identified explicitly as a Pinkerton agent, and the tactics he uses are described in terms that suggest Conan Doyle had been reading the Pinkerton source material closely. By that point, Alan himself had been dead for several years, but his fictional avatars were walking around in some of the most popular crime fiction ever written. The pulp detective fiction of the 1920s and 1930s, the genre that would later be called noir, drew on the same well.
Starting point is 01:28:16 Dashal Hammett, who wrote the Maltese Falcon and The Thin Man, and created the archetype of the tough, wise-cracking American private eye, actually worked as a Pinkerton agent himself for several years in the 2010s and 1920s. His fiction was informed by real experiences in the agency, and the sensibility of his detective characters, their cynicism, their professionalism, their complicated relationships, their complicated relationship with the police and with their own clients. Came directly from the culture of the Pinkerton office. Raymond Chandler, who never worked for the agency himself but Red Hammett, and absorbed the type,
Starting point is 01:28:50 carried it forward into the 1940s and 1950s. By the time television got hold of the private eye figure in the 1960s and 1970s, the character had travelled through three generations of American popular culture, and the fingerprints of Alan Pinkerton were still faintly visible on him if you knew where to look. The most famous and most valuable piece of marketing Alan ever produced, however, was not a book at all. It was a photograph. In October of 1862, shortly after the Battle of Antietam, a Scottish-born photographer named Alexander Gardner traveled to the battlefield to document the scene. Gardner had originally worked for the more famous war photographer Matthew Brady before striking out on his own,
Starting point is 01:29:32 and he was in the process of producing what would become one of the most important photographic collections of the Civil War. President Lincoln had travelled out from Washington to confer with General McClellan about the failure to pursue the retreating Confederate Army, and the meetings took place in and around a commanding officer's tent near the battlefield itself. Gardner took a series of photographs of Lincoln during this visit. Several of them have become famous in their own right, including one in which Lincoln stands tall and gaunt in his stovepipe hat, towering over a cluster of officers. But one particular image, taken outside the tent in a quiet moment, during the visit, featured just three men. Lincoln stood in the centre, recognisable and dominant.
Starting point is 01:30:16 To one side stood General McClellan. To the other side, slightly shorter and looking directly at the camera with the serious expression of a man who had absolutely no intention of smiling, stood Alan Pinkerton, still operating under his wartime identity as Major E.J. Allen, but now with his face preserved for posterity and close physical proximity to the President of the United States. photograph was taken for documentary purposes. Gardner was creating a historical record. He was not, as far as anyone knows, trying to help Alan build his business. But once the image was printed and distributed, Alan understood immediately what he was looking at. It was a certified piece of visual evidence that he, Alan Pinkerton, had personally
Starting point is 01:30:58 worked with Abraham Lincoln and George B. McClellan at one of the most dramatic moments of the Civil War. No competitor could produce anything remotely like it. No other detective agency in America had a photograph of its founder, standing next to the president on a battlefield. It was, in modern marketing terms, an absolute unicorn, and Alan recognized that it was worth its weight in pure gold. He obtained copies, or had copies made, or both, and he began sending the photograph to prospective clients. When a railroad executive wrote to the agency inquiring about services, the response would sometimes include, discreetly, a print of the antietam image. The message was not subtle and was not meant to be. This is the kind of man you are hiring.
Starting point is 01:31:43 This is the level of access he has. This is the kind of organisation you're dealing with. No one else in the private security business could make that claim with a photograph to back it up, and Alan milked this advantage for the rest of his career. The image appeared in his books, in pamphlets about the agency, in his personal correspondence, and eventually in posthumous collections of Pinkerton materials that circulated among clients well into the 20th century. Competitors, of course, tried to copy him. The brand he had built, with the unblinking eye and the slogan and the blue-suited operatives and the carefully managed public image, became the template that every
Starting point is 01:32:18 aspiring private detective agency in America wanted to imitate. By the 1880s, there were Pinkerton adjacent agencies in most major American cities, some of them staffed by former Pinkerton employees who had left the parent company to set up their own operations, and most of them deploying logos, slogans and marketing strategies that were transparent knock-offs of the original. One competing agency used a logo that was essentially the Pinkerton Eye turned slightly sideways. Another adopted the slogan Always Alert, which was so close to We Never Sleep that a serious effort at disguise had apparently not been made.
Starting point is 01:32:53 Alan tolerated most of this with the attitude of a man who knew that imitation, however clumsy, was really just an endorsement of the original. He had set the standard. Everyone else was trying to match it and mostly failing. Where he did take action, he took it in the courts. The Pinkerton name, once it was registered as a trademark, was defended aggressively by the agency's lawyers, and several unsuccessful attempts by competitors to pass themselves off
Starting point is 01:33:19 as authorised Pinkerton operations ended in legal judgments that reinforced the brand's exclusivity. The modern concept of trademark law was still developing in the late 19th century, and Allen's agency was one of the early test cases that helped establish how a commercial name and visual identity could be legally protected from infringement. In this, as in so much else, the Pinkerton's were ahead of the curve in ways
Starting point is 01:33:42 that later institutions would quietly borrow from. The books, the photograph, the logo, the slogan, and the uniform all worked together to create something that had never quite existed before, which was a private business with a fully developed public personality. Most 19th century American companies did not have this. Most of them had names, products, prices and addresses, dresses, and that was about it. If you asked the average American in 1880 what the personality
Starting point is 01:34:10 of the Pennsylvania Railroad was, or what the personality of the First National Bank of Boston was, they would have stared at you blankly, because such a question made no sense. Companies did not have personalities. Companies had ledgers. But if you ask the same American what the Pinkerton Detective Agency was like, you would probably get a detailed answer, drawn from some combination of their books, their advertisements, their agents, and the cultural reputation they had built. The agency was one of the first modern brands in the fully recognisable sense of the term, and the techniques Alan used to build it were absorbed, consciously or not, by the public relations professionals who would invent the formal discipline decades later.
Starting point is 01:34:52 The agency's promotional materials, which have survived in considerable volume in various archives, are genuinely fascinating to examine. They were produced with what was, for the time, unusually high printing quality. They used illustrations rather than just text. They included testimonials from prominent clients, with names and positions spelled out so that prospective new clients could verify the references. They featured reproductions of the famous eye logo, sometimes in color, sometimes in striking black and white, sometimes enormous and occupying most of a page. They contained case summaries, though always carefully sanitised to protect client confidentiality, which served as a kind of informal resume for the agency. They laid out the ethical principles under which the agency
Starting point is 01:35:37 operated, the ones we covered in an earlier chapter, and they made much of the fact that Pinkerton agents were paid by the day rather than by the bounty, a selling point that the competing agencies could not match without changing their entire business model. The tone of all this material was carefully calibrated. It was confident without being boastful, detailed without being tedious and professional without being stiff. Alan understood that the people he was trying to attract as clients were themselves serious men running serious businesses, and they did not want to work with the service provider who sounded like a carnival barker. They wanted a vendor who sounded like themselves, which is to say, sober, competent, and focused on results. The marketing materials
Starting point is 01:36:21 produced by the Pinkerton Agency read, by and large, like the internal memoranda of a bank or a railroad, which was exactly the tone the potential customers were most comfortable with. What Alan was doing, in essence, was inventing a new category of commercial communication, one that sat between the old-fashioned business circular and the modern advertisement. The agency's materials did not simply list services and prices. They told stories. They established personality. They created emotional associations between the brand and desirable qualities like reliability,
Starting point is 01:36:53 discretion, and competence. They did this in ways that made the reader want to be associated with the agency, because being a Pinkerton client was itself a marker of seriousness, much as, in a later era, being represented by certain prestigious law firms would be a marker of seriousness. The agency had achieved something that most businesses never achieve, which was the ability to confer status on its customers through the simple act of selling them services. There was one more layer to the strategy that deserves mention, which was the cultivation of favourable press coverage. Alan understood that newspapers were the dominant mass medium of his era, and he worked diligently to ensure that the
Starting point is 01:37:32 coverage of his agency was, on balance, positive. He cultivated relationships with sympathetic reporters in major cities, provided exclusive access to the details of successful cases in exchange for flattering write-ups, and, when necessary, offered correction and clarification to stories he considered inaccurate. The agency was not above quietly leaking information about pending cases to favoured newspapers, timing the revelations to coincide with the arrest so that the Pinkerton role would be front and centre
Starting point is 01:38:03 in the resulting coverage. In the pre-internet age, this kind of careful management of press relationships was the closest thing available to modern public relations, and Alan was among the first American businessman to pursue it systematically. The result of all this accumulated effort was an agency whose public profile
Starting point is 01:38:20 was, in the final two decades of the 19th century, wildly out of proportion to its actual size. The Pinkerton Agency was, at any given time, a relatively modest business by the standards of the industrial era. It had a few hundred agents on its payroll, a few dozen field offices, and revenues that, while substantial, were tiny compared to the great railroad corporations or the emerging industrial trusts of the same period. But its name was known to literally everyone in America who could read, its logo was one of the most recognisable in the country, and its reputation for effectiveness had been so thoroughly established that potential clients often hired it on the strength of that reputation alone, without any detailed negotiation over what
Starting point is 01:39:03 specific services would be provided. There was, inevitably, a downside to this level of public recognition, and Alan was aware of it. The more famous the agency became, the harder it was to conduct undercover operations, because any suspect with a newspaper subscription knew what a Pinkerton agent looked like, how he operated, and what tactics he might use. This is why the agency increasingly recruited agents who did not match the stereotype. Agents from immigrant communities who spoke languages other than English. Agents whose physical appearance did not suggest the typical detective look. Agents who could blend into environments where the famous blue suit would have been a dead giveaway. The public image that Alan had so carefully cultivated,
Starting point is 01:39:46 became, paradoxically, an operational liability for the fieldwork, which had to be continually adapted to stay a step ahead of a public that knew too much about what the agency was supposed to look like. Through all of this, the agency kept growing. New offices opened in Philadelphia, New York, Boston, and eventually as far west as Denver and San Francisco. The client list expanded from railroads and express companies into banking, industrial manufacturing, mining, and eventually, as we will see in later chapters, into the fraught territory of labour disputes, where the reputation Alan had built would come to be used in ways that he probably did not originally anticipate, and might not, in his earlier years, have endorsed. But that part of the
Starting point is 01:40:30 story is still ahead. In the 1870s and early 1880s, while Alan was still at the peak of his personal influence and still shaping the agency's image with his own hands, the focus was elsewhere. It was on the outlaws of the expanding frontier, on the train robbers who were making American railroads a daily adventure, on the bank gangs whose escapades were filling the newspapers, and on the pursuit of those outlaws by Pinkerton agents, across territories that were only loosely governed and frequently dangerous. The Scottish Cooper, now in his 60s, sat in his Chicago office reading the reports that came back from the field, occasionally shaking his head at the casualties, and dispatching fresh agents
Starting point is 01:41:10 westward on trains that were themselves potential targets for the very criminals those agents were being sent to catch. The age of the Pinkerton as frontier pursuer was in full swing, and it would soon produce some of the most famous and some of the most controversial operations in the agency's history. A raid on a farmhouse in Missouri was coming. An obsessive pursuit of a group of bank robbers across two continents was coming. A reputation, carefully cultivated through books and photographs, was about to be tested against the real and much messier reality of chasing armed men through territory where the law was thin, and the consequences of miscalculation were severe. The myth and the reality were about to collide, and the agency's image so carefully
Starting point is 01:41:53 polished, was about to discover that even the most brilliant marketing campaign cannot always protect a company from the decisions its own agents make in the field. The end of the Civil War did not bring the tidy, peaceful return to normal life that the Victoria's Union had imagined. Armies were demobilised. Hundreds of thousands of men were handed back their civilian clothes and a small severance payment, and they were expected to quietly resume the lives they had led before 1861. A great many of them did exactly that, returning to farms, workshops and small towns where their families had been waiting for them. A smaller but significant group, however, found that peacetime civilian life did not fit them particularly well anymore.
Starting point is 01:42:34 They had spent four years sleeping rough, carrying weapons, and taking property from strangers under colour of military authority. The habits had set in, the skills had become reflexes, and the economic opportunities waiting for them at home, especially in the devastated South and in the border states that had seen the worst of the guerrilla fighting, were not exactly abundant. The railroads, meanwhile, were expanding at a pace that the country had never seen before. Track was being laid across plains and mountains at something like five miles a day during the peak years. Banks were proliferating in small towns that had barely existed before the war.
Starting point is 01:43:09 Express companies were moving enormous sums of money across enormous distances, often through territory where the nearest peace officer was 100 miles away and severely outgunned. For a demobilized soldier with a pair of revolvers, a good horse, and no particular prospects, the math was not subtle. A single successful train robbery could pay better than 10 years of farm labour, and the chances of getting caught, if you picked your target carefully, were genuinely not that bad. The first serious demonstration of this new mathematics came from Indiana in 1866 when a group of brothers and cousins named Reno decided that the steadily expanding Ohio and Mississippi Railroad was offering them a business opportunity. On October evening in that
Starting point is 01:43:52 year, the Reno gang, as they would come to be called, boarded a passenger train at a small station in Jackson County, drew their weapons, forced the express messenger to open the the safe, took the money and jumped back off the train. This was not technically the first robbery of a train in world history, because there had been a few scattered incidents involving stopped trains at stations before. But it was arguably the first true train robbery of the American type. The type where an armed gang boarded a moving train, controlled the passengers, opened the express car and made their escape. The model had been invented. Others would follow in their thousands. The express companies who were footing the bill for all this were the first to respond.
Starting point is 01:44:33 Adam's Express Company, our old client from the earlier chapters, had already been a Pinkerton customer for 15 years, and they turned to the agency immediately. Allen accepted the contract and began deploying agents to Indiana, where they spent several months tracking the Reno gang through a landscape of sympathetic relatives, remote farmsteads, and corrupt local officials who had been quietly bought off. The investigation was slow, methodical, and by the standards of the agency perfectly routine. Within about a year and a half, most of the gang had been identified, several members had been captured, and the agency was in the
Starting point is 01:45:08 process of closing out the case. The case closed itself, more abruptly than Alan would have preferred, through the intervention of a local vigilance committee in southern Indiana. Several members of the Reno gang, while being held in a local jail awaiting trial, were dragged out by masked men and hanged from a nearby tree. The agency, which had worked hard to build the legal cases that would have sent the gang to prison through proper channels, now found itself facing uncomfortable questions about whether it had tacitly encouraged or simply failed to prevent what amounted to mob murder. Alan, for his part, issued a statement condemning vigilantism and insisting that the agency had had no role in the lynchings, which was almost certainly true in the literal sense, and somewhat
Starting point is 01:45:51 more complicated in the moral sense. The early years of the agency's pursuit of train robbers had, in their very first major case, already run into the kind of ethical fog that would characterize so much of the work that followed. The Reno gang was only the beginning. Within a few years, similar outfits were operating across most of the states west of the Mississippi, and the Pinkerton Agency was being hired by almost every major railroad and express company to chase them. The work was slow, dangerous, and often frustrating. Field agents might spend six months in a boarding house in a small Kansas town waiting for a suspect to return, only to discover that the suspect had moved to Texas three months earlier.
Starting point is 01:46:31 Informants had to be cultivated, paid and protected, which was not always possible. Witnesses had to be persuaded to testify against armed men, whose relatives often lived down the street and had long memories. The files in Chicago grew thicker, and the agency's reputation as the premier private law enforcement organization in the country grew along with them. Then, in the early 1870s, the agency began to pursue a pair of Missouri brothers, whose exploits would turn into the single greatest public relations catastrophe in the history of the company. Their names were Jesse and Frank James. They were former Confederate guerrillas who had ridden with the irregular forces of William Quantrill and Bloody Bill Anderson during the Civil War, and the transition from guerrilla fighter to peacetime bank and train robber
Starting point is 01:47:14 had been, for them, remarkably smooth. With a rotating cast of cousins, wartime comrades and assorted friends, they spent the years after the war carrying out a series of high-profile bank and train robberies across Missouri, Kansas, Iowa, and neighboring states. What made the James Brothers particularly difficult to catch, as opposed to the many other outlaw gangs of the same era, was the genuine popular sympathy they enjoyed in parts of rural Missouri. The civil war had not exactly ended cleanly in the border states.
Starting point is 01:47:45 Missouri had been a deeply divided state during the war, with neighbors' killing neighbours over political loyalties, and the Union victory had left a considerable population of former Confederates, who nursed grievances and considered themselves occupied rather than liberated. The James Brothers presented themselves through sympathetic journalists and their own public letters as persecuted former Confederate soldiers who were being harassed by northern banks and railroads, and who were simply giving back to the powerful interest that had ruined ordinary southern farmers. This was, to put it charitably, a very creative interpretation of the the actual robberies, which tended to involve shooting unarmed bank clerks,
Starting point is 01:48:22 terrifying passengers, and making off with other people's savings. But the narrative had genuine traction in certain quarters, and it made the brothers almost impossible to track in their home territory because ordinary farmers along their routes would not talk to investigators under any circumstances. The agency took the case seriously. Adams Express and several major railroads were losing enormous sums of money to the gang's operations, and the professional embarrassment of failing to catch them was mounting. Alan personally supervised the Missouri operations,
Starting point is 01:48:54 sending in multiple agents over a period of several years, losing several of them to gang members who seemed always to know where the investigators were and what they were doing. At least two Pinkerton agents, John Witcher in 1874, and Louis Lull in the same period, were killed while working undercover in Missouri trying to get close to the James family. The agency became, in Alan's eyes, personally invested in the case.
Starting point is 01:49:15 It was no longer just a commercial contract. It was a matter of professional pride and of avenging fallen colleagues, and the combination of those two motivations was to prove an unfortunate one. The decision Alan made in the winter of 1874 to 1875 was the worst of his career, and it was made by a man who was 60 years old, still recovering from a serious stroke he had suffered several years earlier and operating under the accumulated frustration of years of failed pursuits. The agency had received intelligence that the James brothers were hiding,
Starting point is 01:49:45 out at the family farm of their mother, Zarelda Samuel, and her second husband, Ruben Samuel, near the small town of Kearney in Clay County, Missouri. The farm was a modest working property, with a main house, outbuildings, and surrounding fields, and it was home not only to Zarelda and Rubin, but also to their children from Zarelda's second marriage, including a nine-year-old boy named Archie Samuel, who was the half-brother of Jesse and Frank. Alan authorized an operation to surround the farmhouse and force the brothers to surrender. The plan, as it was originally conceived, involved quietly approaching the property at night, deploying agents around its perimeter, and either capturing the brothers as they tried to flee
Starting point is 01:50:26 or forcing them to give up through the threat of overwhelming numbers. What actually happened, on the cold night of January 26, 1875, bore only a partial resemblance to the plan. The agents approached the farm in darkness, as planned. They positioned themselves around the main house, as planned. And then, for reasons that have been debated by historians ever since, they threw an incendiary device through one of the windows of the house. The device was apparently intended as a combination illumination flare and smoke generator, something that would light up the interior of the house,
Starting point is 01:51:01 so the agents could see who was inside, and possibly forced them to flee outside where they could be captured. It was not, or so the agency later insisted, intended as an explosive. Ruben Samuel saw the burning object land on the floor of the kitchen, and, in a reasonable but catastrophic decision, pushed it into the fireplace with a stick to keep it from setting the room on fire. The device, whatever it was, did not behave like an ordinary flare when it hit the hot coals. It detonated. The explosion tore apart the fireplace, sent fragments of metal and stone across the kitchen, and wounded everyone in the room. Zarelda Samuel, standing near the fireplace,
Starting point is 01:51:38 was struck by a large piece of shrapnel that destroyed her right arm so badly that it had to be amputated at the elbow later that night. Her nine-year-old son Archie, standing closer to the fireplace, was struck by fragments that caused injuries so severe that he died within hours. The agents, hearing the explosion and the screams, realized almost immediately that something had gone very wrong.
Starting point is 01:52:02 They searched the house, discovered that the James brothers were not actually there and had not been there for some time, and withdrew from the property. The operation that was supposed to end the agency's pursuit of the most wanted outlaws in America had instead killed a child, maimed a woman, and left the actual targets untouched. The reaction, when the news spread, was something the agency had never experienced before. This was not the familiar criticism of detective methods
Starting point is 01:52:28 or the occasional editorial complaint about overzealous pursuit. This was a wave of public outrage that swept across Missouri, spread to the rest of the country through sympathetic newspaper coverage and transformed the James Brothers overnight from successful outlaws into American folk heroes. The image of a one-armed grieving mother became an icon of Confederate martyrdom. The dead child was eulogized in poems and newspaper columns.
Starting point is 01:52:55 The Pinkertons, who had entered the operation as the righteous pursuers of murderous bank robbers, emerged as the villains of a story that now seemed to be about the persecution of an innocent farm family by outside forces. The Missouri State Legislature actually passed, or came very close to passing, a resolution praising the James Brothers as defenders of their home territory and condemning the Pinkerton's as out-of-state interlopers. A bill offering the brothers' amnesty for their past crimes came within a few votes of becoming law. Jesse James himself wrote a long and self-righteous letter to a Missouri newspaper, comparing the attack on his family home to the atrocities committed by Union guerrillas during the war, and positioning himself,
Starting point is 01:53:34 as a victim of continuing northern aggression, rather than a common thief. The letter was published, widely read, and reprinted in sympathetic newspapers across several states. Alan was, by most accounts, genuinely devastated by the outcome. He had not intended to kill a child, and the evidence suggests that the incendiary device was not meant to explode the way it did. But the distinction between intention and outcome did not matter to the public, and it arguably should not have mattered. The operation had been authorised by Alan. The device had been brought to the farm by his agents.
Starting point is 01:54:09 The child had been killed. Whatever the intended mechanism, the responsibility was clear, and Alan carried the weight of it for the rest of his life. He wrote privately to colleagues about his regret, and he refused in later interviews to apologise publicly for the operation itself, because he believed that to apologise would be to hand the James brothers a further propaganda victory. But he also never again authorised a similar operation.
Starting point is 01:54:33 and the internal procedures of the agency were changed after the Kearney disaster to require much more rigorous intelligence verification before raids on private homes. The James Brothers continued to operate for another seven years, and the Pinkertons continued to pursue them, but the relationship had been permanently altered. After Kearney, the agency pursued the brothers more cautiously, with less public profile, and increasingly through cooperation with local law enforcement,
Starting point is 01:55:01 rather than independent action. When Jesse James was finally killed in 1882, it was not by a Pinkerton agent, but by a member of his own gang named Robert Ford, who shot him in the back of the head in his home in St Joseph, Missouri, in exchange for a reward. Frank James surrendered a few months later and eventually, after two trials that both resulted in acquittals due to jury sympathies, lived out the rest of his life as a free man. The Outlaw saga ended. The public image of the James brothers as folk heroes, however, outlived them by decades and as a story. proven, in its own way, remarkably durable. Every generation since has produced new books, new films and new songs about the James Brothers, and in a remarkable number of them, the Pinkerton's remain the unambiguous villains. The lesson Alan drew from the Kearney
Starting point is 01:55:49 disaster was a practical one, direct confrontation with entrenched outlaw gangs in territory, where the local population was hostile to outside investigators was a dangerous and often counterproductive approach. Far better, he concluded, to invest in long, long-term undercover operations, patient intelligence gathering, and the careful cultivation of informants inside the gang itself. This philosophical shift would come to define the agency's approach to the second great wave of Western Outlaws that appeared in the 1890s, and it would produce some of the most sophisticated investigative work the agency ever performed. The most famous of those operations was the long hunt for the loose confederation of bank and train robbers, known collectively
Starting point is 01:56:30 as the wild bunch, led by a soft-spoken Utah-born outlaw named Robert Leroy Parker, who had adopted the alias Butch Cassidy in his 20s, and had, by the time the Pinkertons began seriously pursuing him, become the most successful train robber in American history. Cassidy was not the stereotypical outlaw. He was reportedly charming, well-mannered, largely non-violent by the standards of his profession, and genuinely popular with the ranching communities in the remote corners of Wyoming, Utah and Colorado. where he sheltered between jobs. His preferred method of train robbery involved extensive advance planning, careful escape routes, and a strong preference for not shooting anybody if it could possibly be avoided.
Starting point is 01:57:12 He was, in short, the kind of outlaw that the pursuing detectives almost had to respect, which did not make him any easier to catch. The Pinkerton agent assigned to the Wild Bunch case was a man named Charles Seringo, who deserves to be remembered as one of the most remarkable figures in the agency's history. Even though his name, he was a man. name has faded considerably in popular memory. Surringo was a former Texas cowboy who had ridden the cattle trails for years before joining the agency in the 1880s. He spoke the language of the ranching communities, understood the code of silence that bound the people of the remote Western territories, and was able to move through environments where a conventional detective would have been
Starting point is 01:57:49 identified as an outsider within about five minutes. Alan had died by the time Seringo joined, and the agency was now being run by Alan's sons, William and Robert. But the operational culture Alan had built continued to dominate how the work was done, and Seringo was in many ways the pure product of that culture. Soringo pursued the wild bunch for the better part of four years, riding undercover through Wyoming and Utah under a series of false identities, sometimes as a ranch hand, sometimes as a horse thief fleeing from the law in Texas,
Starting point is 01:58:20 sometimes as a travelling cattle buyer looking for stock. He befriended outlaws, slept in the same bunkhouses as wanted men, attended dances in remote towns where members of the gang were likely to appear and compiled over time one of the most comprehensive intelligence files on the wild bunch that has ever existed. He obtained rare photographs of gang members and their associates, including a celebrated photograph of five members of the gang posed together in a studio in Fort Worth, Texas, a photograph that would become one of the defining visual documents of the Western Outlaw era.
Starting point is 01:58:53 He also obtained photographs of some of the women connected to the gang, including the famous but still mysterious figure known as Etta Place, who was the travelling companion of Butch Cassidy's right-hand man Harry Longabour, better known by his nickname the Sundance Kid. Etta Place herself remains one of the great unsolved mysteries of the American West. Nobody, even today, knows her real name, her place of birth, her family background, or what happened to her after the gang's final years. The surviving photographs show an elegant, self-possessed young woman
Starting point is 01:59:24 who could have passed for a society lady in any major city, and the scattered references to her in contemporary documents describe her as intelligent, educated and completely devoted to Sundance. The Pinkerton files on her are frustratingly thin, because even the agency's patient investigators could not penetrate her identity. She appears, moves through the story, and disappears again, leaving behind only a handful of photographs and a long unresolved question mark. Soringo's patient work eventually produced enough intelligence to put serious pressure on the wild bunch,
Starting point is 01:59:58 and the gang's operations in the United States became progressively more difficult to execute, as railroad companies hired additional guards, banks upgraded their vaults, and the Pinkerton files on individual gang members made them easier to identify and track. By 1901, Butch Cassidy and Sundance had concluded quite reasonably that continuing to operate in the American West was a game they were going to lose if they played it much, longer. They made the unusual decision to emigrate. Specifically, they sailed, along with Etta Place to South America, where they settled briefly in Argentina and attempted to live as legitimate ranches on a spread in Patagonia. The Pinkertons did not, as has sometimes been claimed,
Starting point is 02:00:40 immediately give chase. The agency did not have operations in South America, and the cost of pursuing the gang to another continent was difficult to justify to American clients, whose concerns did not extend south of the Rio Grande. The agency did, however, maintain contact with Argentine and Bolivian authorities sharing information about the Americans who are now ranching in Patagonia, and this information would eventually play a role in the gang's final unraveling. After a few years of attempted legitimate life, Cassidy and Sundance apparently concluded that ranching was both harder and less lucrative than robbery,
Starting point is 02:01:15 and they returned to their old profession in South America, knocking over mining company payrolls in the occasional Bolivian bank. This was, predictably, a short-lived second act. The most widely accepted account has them dying in a gunfight with Bolivian soldiers in the town of San Vicente in 1908. Though, as with all famous outlaw deaths, alternative theories have persisted for over a century, with various writers claiming that one or both men survived and returned to the United States under assumed identities to live out long, quiet lives.
Starting point is 02:01:45 The evidence for these claims ranges from thin to non-existent, but the persistence of the theories tells us something about the enduring hold of the wild bunch on the American imagination. Etta Place's fate is even more mysterious. She travelled back and forth between South America and the United States several times during the gang's Patagonian years, and at some point she simply vanished from the historical record. Some accounts say she returned to the United States and settled in the West under an assumed name. Others say she returned to her original identity, whatever it was, and lived the rest of her life
Starting point is 02:02:18 in anonymity. The Pinkerton files, when consulted for clues, offer only a few fragmentary references, none of them conclusive. She's one of the great vanishing figures of the American Outlaw era, and she vanished so completely that even the most determined detectives of her time could not find her. The Wild Bunch Pursuit, taken as a whole, was in many ways the Pinkerton agency at its best, It involved patient undercover work, meticulous intelligence gathering, extensive collaboration with multiple law enforcement agencies, and a willingness to pursue suspects across vast geographical distances over a period of many years. The files syringo compiled, with their photographs, aliases, known associates,
Starting point is 02:03:02 and detailed biographical information were a direct descendant of the criminal archive Alan had invented back in the 1850s, scaled up for the much larger and more mobile criminal underwomenes, world of the industrial age. The operation demonstrated that the agency had learned from the Kearney disaster, had shifted toward patient investigation rather than violent confrontation, and had developed capabilities that no other private or public investigative body in North America could match. But the operation also demonstrated something else, something that would become increasingly uncomfortable as the 19th century turned into the 20th. Public opinion in the Western territories, particularly among ordinary ranches and small-town residents,
Starting point is 02:03:43 had shifted in a way that was not favourable to the agency. The Pinkertons, who had once been seen as useful outsiders bringing order to lawless territories, were increasingly seen as hired guns working for the railroads and the banks against the interests of ordinary people. The railroads were hated in much of the rural West because they controlled shipping rates, displaced homesteaders, and charged monopoly prices for the only transportation available.
Starting point is 02:04:08 The banks were mistrusted because they foreclosed on farms during bad years and seemed to grow rich while the people around them struggled. And the Pinkerton's, who were paid by both, were increasingly lumped together with their clients in the public imagination. This shift in public perception mattered. It made recruiting local informants harder. It made conducting investigations in hostile territories more dangerous. It made juries less willing to convict criminals
Starting point is 02:04:33 when Pinkerton testimony was the principal evidence. And it set up, though nobody in the agency fully understood this at the time, the far larger catastrophe that would overtake the Pinkerton reputation in the coming decades, when the agency's clients began to include not just railroads and banks, but the owners of the mines and factories of the Industrial East, and the work they were hired to do began to involve not the pursuit of bank robbers, but the management of strikes, the infiltration of labour unions, and the application of armed force against their client's own employees.
Starting point is 02:05:03 The transition from frontier pursuer to industrial enforcer was already well underway by the time Charles Soringo was riding through Wyoming under his various false names, the economic structure of the United States was changing rapidly. The country was becoming a nation of factories and mines rather than farms and railroads, and the Pinkerton Agency, with its accumulated expertise in surveillance, undercover work and organised private force, was being hired to apply those skills to a new and much more politically fraught set of problems. The Scottish Cooper, who had built the agency, was long gone, having died in 1884.
Starting point is 02:05:38 and the agency he left behind was now being steered by his sons and their professional management team into waters that Alan himself might not have recognised. The next chapter of the story, in other words, would not take place on the dusty plains of Missouri or the remote canyons of Utah. It would take place in the coal fields of eastern Pennsylvania, in immigrant communities where a different kind of desperation was producing a different kind of organized response, and where a young Pinkerton agent with a false Irish name was about to infiltrate a society whose very existence. would later be argued over by historians for the next 150 years. The agency was leaving the frontier behind and entering the industrial heartland,
Starting point is 02:06:17 and the reputation it had earned chasing outlaws was about to be transformed into something considerably darker. To understand what happened in the coal fields of eastern Pennsylvania in the 1870s, you first have to understand the economic structure that had been built there, because without that structure, the rest of the story simply does not make sense. the Industrial Revolution had arrived in the United States with a kind of breathless enthusiasm, transforming a country of farms, workshops and small towns into a country of factories, mines, and rail yards. The transformation was impressive if you looked at the aggregate numbers,
Starting point is 02:06:53 and genuinely appalling if you looked at the people whose lives had been rearranged to make the numbers add up. Nowhere was this more true than in the anthracite coal region of Pennsylvania, a stretch of mountainous country west of Philadelphia, where some of the richest deposits of hard coal in the world had been discovered and were now being extracted at a pace that had never been seen before. The coal industry of the 1860s and 1870s was dominated by a small number of extremely wealthy companies, most of which also owned the railroads that carried the coal out of the mountains to the cities and ports where it would be burned.
Starting point is 02:07:27 The most powerful of these companies, the Philadelphia and Reading Railroad under its President Franklin Gower, had consolidated enormous holdings in both mining and transportation, which meant it could control both the production and the shipping of coal across most of the region. Gowan was ambitious, intelligent, and possessed of a kind of executive ruthlessness that even his contemporaries found a bit much. He had been a lawyer before he was a railroad president, and he thought about labour relations the way a lawyer thinks about opposing counsel.
Starting point is 02:07:57 The men who worked in his minds were not in his view, employees in any meaningful human sense. They were inputs to a production process, and like all inputs, they were to be obtained at the lowest possible cost. The system that Gowan and his fellow coal barons had perfected, and that was being imitated by mine and mill owners across much of the industrial eastern United States, was built around a deliberate economic isolation of the workforce.
Starting point is 02:08:21 A miner in one of the small Pennsylvania coal towns of this era did not simply work for the company. He lived in a house that was owned by the company, He bought his food at a store that was owned by the company. His children attended a school that was built by the company, often taught by a teacher whose salary was paid by the company. When he was sick, he was treated by a doctor who was employed by the company. When he went to church, he attended a building that was sometimes constructed on company land with company money.
Starting point is 02:08:49 Every aspect of his daily life, from the roof over his head to the bread on his table, to the medicine in his child's spoon, passed through the accounting department of the mine that also cut his paycheck. The most remarkable feature of this arrangement, and the one that historians have spent the most time explaining, was the system of payment. Many of the coal companies did not pay their workers in actual United States currency. They paid them in a form of private company money, variously called script chits, tokens or company coupons, depending on the particular mine and the particular moment. The script was essentially a promissory note issued by the company,
Starting point is 02:09:26 redeemable only at the company store and not accepted as legal tender by any outside business. A miner who received his wages in Scrip on Friday evening could not take that script to the nearby town and buy groceries from an independent grocer because the independent grocer would refuse it. He could not deposit it in a bank
Starting point is 02:09:45 because the bank would not accept it. He could not save it for long-term purposes because its value depended entirely on the continuing cooperation of the company that issued it. What he could do with the script was walk down the road to the company store and exchange it for flour, salt pork, boots, kerosene,
Starting point is 02:10:03 and whatever else the store happened to be selling that week, at prices that were, unsurprisingly, not exactly competitive with the prices charged at independent stores in nearby towns. The results of this arrangement were predictable and were also, from the perspective of the mine owners, entirely the point. A miner paid in Scrip had no way to accumulate savings
Starting point is 02:10:24 in a form that gave him independence from his employment, employer. He could not easily quit his job because his savings, such as they were, existed only in the form of credit at the company store, which would evaporate the moment he left the company's employ. He could not easily move to a different town because his housing was tied to his employment and his money was not portable. Rent for his company-owned house was deducted directly from his paycheck before he ever saw the remainder. Charges at the company doctor were deducted. Charges at the company's store were deducted. Not infrequently, a miner would reach the end of a pay period and discover that his net earnings for the month, after all deductions, were either zero or a small negative number, meaning he now owed the company money that would be deducted from his next month's wages before he received them.
Starting point is 02:11:10 This was not technically slavery, because the miners were not literally owned by the companies and could in principle walk away if they were willing to leave behind their housing, their credit, and everything else they had. But the distance between this system and slavery was, for practical purposes, considerably smaller than the official legal classification suggested. The word that was used by contemporary critics was peonage, a term borrowed from the Spanish-speaking Americas where similar systems had operated for centuries, and the term captured the essential reality reasonably well. A miner in an anthracite company town in 1870 was a free man in the narrow legal sense, and a dependent bound to a single employer in almost every practical sense, and the gap between those two statuses was maintained primarily through the design of the payment and housing arrangements. The miners who worked under this system were not, by and large, the native-born American Protestants who had dominated the early decades of the industrial workforce. They were, in overwhelming proportions, recent immigrants from Ireland, Wales, Germany,
Starting point is 02:12:13 and a handful of other European countries, with Irish Catholics forming the single largest group in most of the anthracite region. reason for this concentration was itself a product of economic forces operating at a continental scale. The Great Famine, which had devastated Ireland in the 1840s and the years immediately following, had produced one of the largest refugee migrations in modern history, with roughly a million Irish people dying of hunger and disease, and another million or so fleeing the country in any direction they could go. A large proportion of those refugees had landed in the eastern ports of the United States,
Starting point is 02:12:48 where they arrived with no money, no property, no English language educations in the accents the American employers preferred, and no particular skills beyond the ability to do hard physical labour without complaint. They had, in other words, arrived in exactly the condition that the coal companies were looking for in a workforce. The conditions in the mines were, on top of everything else, genuinely terrible. Anthracite mining in the 19th century was one of the most dangerous occupations in the industrial world. Kavins killed. minors regularly. Methane explosions killed them in large batches when they killed them at all. Black lung disease, which was poorly understood at the time but well attested in the lives of
Starting point is 02:13:28 the men who worked underground, shortened lifespans by years or decades. Children as young as eight or nine worked in the breaker rooms, sorting coal by hand in conditions of perpetual dust, for wages that would not today be considered adequate for an hour's labour. Adults worked ten or 12-hour shifts underground, came home covered in coal dust, and were too exhausted to do much more than eat, wash partly, and sleep before returning to the mine the next morning. In this combination of economic dependence, ethnic and religious isolation and physical brutality, something was inevitably going to give. What gave, starting around the 1860s and intensifying through the 1870s, was that the miners began to organise. They formed mutual aid societies
Starting point is 02:14:15 to pay funeral expenses when their co-workers died. They formed Catholic fraternal organisations that provided social and cultural spaces outside the direct control of the company. They formed eventually early labour unions that tried to bargain collectively for better wages and safer conditions, and in some of the more embittered communities, they formed secret societies whose purposes were not entirely clear even to outsiders at the time, and that have remained somewhat obscure to historians ever since. One such society, or alleged society, was known as the Molly Maguire. The name itself was borrowed from an Irish peasant resistance movement of the 1830s and 1840s, which had operated in rural Ireland against the estate managers and landlords of the English gentry,
Starting point is 02:14:58 using threats, sabotage, and occasional violence to resist evictions and extract better terms for tenant farmers. Whether the Pennsylvania version of the Molly Maguire was a direct organizational descendant of the Irish original, a loose imitation inspired by the old name, a genuine secret society with formal membership and rituals, or a largely imagined construct that the mine owners exaggerated for their own purposes, is a question that has been debated for 150 years and shows no signs of being settled. What is clearly documented is that a campaign of intimidation against mine supervisors did take place in the anthracite region during the late 1860s and early 1860s. 70s that threatening letters were sent to company officials, that a small number of foremen
Starting point is 02:15:45 and superintendents were assaulted or killed, and that the mine owners became convinced, or at least publicly claimed to be convinced, that a coordinated conspiracy of Irish miners was responsible. The important thing to understand about all of this, and the thing that often gets lost in the more dramatic retellings of the subsequent events, is that the economic structure created the conditions for the violence, not the other way around. A community of immigrant workers, trapped in a system designed to extract their labour, while preventing them from accumulating independent resources, confronting genuinely dangerous working conditions
Starting point is 02:16:19 under which their co-workers routinely died, with no political power, no recognised union, no access to the local political system, which was dominated by the same business interests that owned the mines, and no legal recourse against the companies that set the terms of their existence produced exactly the kinds of responses that desperate communities tend to produce under those conditions. Some turned to the Catholic Church for consolation, some turn to alcohol, some turn to organised labour, and some apparently turned to secret societies that use threats and occasional violence
Starting point is 02:16:51 to try to shift the balance of power in some small way. The question of whether any of this amounted to a coordinated conspiracy in the way the mine owners later claimed was in the end the question that the Pinkerton Agency was hired to answer. Franklin Gowan, the Railroad and Mining President we met earlier, was the man who hired them. He had concluded that the combination of early labour organising and the alleged Molly Maguire violence was an existential threat to the business model of the Philadelphia and Reading Railroad, and he wanted the whole thing broken. He travelled to Chicago, met with Alan, and asked for the agency's most skilled undercover operative
Starting point is 02:17:26 to be placed inside the Irish mining communities of Squillkill County for as long as it took to gather evidence that could be used in court. The contract was accepted. The agent selected was a young Irish Catholic immigrant named James McParlane, who had been born in County Armagh, had emigrated to the United States in his 20s, had worked various jobs, including a stint as a liquor store clerk, and had joined the Pinkerton Agency in 1871. McParland was in his late 20s, physically unremarkable,
Starting point is 02:17:55 and possessed of exactly the background that would allow him to pass convincingly as a working-class Irish immigrant looking for a job in the mines. McParlane arrived in the Anthracite region in October of 1873, operating under the assumed name of James McKenna. He presented himself as a counterfeiter and general fugitive on the run from authorities in other states, which was a choice of cover story designed to give him instant credibility in the rougher Irish Catholic taverns and to explain why he was looking for informal work in remote mining towns, rather than pursuing legitimate employment through normal channels. He settled in the town of Shenandoah, began drinking in the local pubs, joined the ancient
Starting point is 02:18:35 order of Hibernians, which was a legitimate Irish Catholic fraternal organisation that some of the alleged Molly Maguire were also members of and began to cultivate relationships with the men he believed to be connected to the secret society. His reports, filed daily and sent back to Pinkerton headquarters in Philadelphia, and ultimately to Allen in Chicago, provide the most detailed surviving account of life inside an Irish mining community in this period, viewed from the perspective of a man whose job was to extract incriminating criminal material from everyone he met. The reports document drinking bouts, fights, political arguments, complaints about mine conditions, jokes, hymns, funerals, weddings, and the full texture of a
Starting point is 02:19:19 community that considered itself under siege by the economic forces controlling its existence. They also document, or claim to document, discussions of violence against mine supervisors, plans for beatings and killings, and the internal workings of what McParlane presented as a coherent conspiracy with identifiable leaders, meeting places and hierarchies of command. Here is where the story gets genuinely complicated, because the critics of the subsequent prosecutions have raised an uncomfortable question that has never been fully answered. The threatening letters, the beatings, and the alleged assassinations had been occurring at a certain background rate in the anthracite region for several years before Macpaland arrived.
Starting point is 02:20:01 The question the critics have asked is whether those incidents increase. significantly during the period when Macpard was embedded in the community and whether McParlane himself, rather than simply documenting an existing conspiracy, had in some ways encouraged or facilitated its expansion through his own presence and influence within the social circles he had penetrated. The evidence on this question is mixed and it will always be mixed because the historical record consists largely of McParlane's own reports which naturally present his behaviour in the most favourable light. What can be established with reasonable certainty
Starting point is 02:20:37 is that the volume of threatening letters and reported acts of intimidation did increase during the two and a half years that MacParlane was undercover, that he was physically present at some of the meetings where violence was allegedly planned, and that in at least a few documented cases
Starting point is 02:20:52 he appears to have done very little to dissuade the men around him from carrying out the actions they were discussing. Whether this constitutes active provocation, passive acquiescence, or simply cautious undercover operative, operational discipline is, to this day, a matter on which reasonable historians disagree. The most notorious single incident of the entire period occurred in December of 1875 at a place
Starting point is 02:21:16 called Wiggins Patch, where a family named O'Donnell lived in a rented company house on the edge of a mining town. Some of the O'Donnell men had been identified, either by McParlane or by other informants working in parallel, as alleged members of the Molly Maguire's, and they were believed to be connected to one or more recent incidents of violence in the region. In the early morning hours of December 10th, a group of approximately 30 masked men, armed and operating with evident organisation, surrounded the O'Donnell House and broke down the doors. What followed was not an arrest, because these men were not law enforcement officers in any legal sense. It was arrayed by a vigilante committee, composed of men whose identities were never officially established, but who clearly
Starting point is 02:21:59 had access to detailed intelligence about who lived in the house and which rooms they slept in. The raiders pulled the occupants out of their beds. They beat the mother of the household severely. They shot and killed a young woman named Ellen McAllister, who was the sister of one of the O'Donnell men and who was visiting the family that week. They also shot James Charles O'Donnell, known locally as Friday. The remaining occupants of the house were either beaten unconscious or forced to flee into the snow-covered fields outside. The vigilantes withdrew as quickly as they had arrived, leaving behind a scene of violence that would have been shocking in any context and was particularly disturbing, given that the raid had killed a young woman who, by every subsequent account, was entirely uninvolved in any mining-related
Starting point is 02:22:47 violence. The incident was never properly investigated by local authorities. No arrests were made, no prosecutions were brought. The identities of the 30 masked men were never officially determined, Though contemporary accounts and subsequent historical analysis have suggested strongly that they included off-duty employees of one or more of the local mining companies, possibly supplemented by members of private security forces attached to those companies. The connection to McParland, while never formally proven, was the subject of considerable suspicion at the time and afterward. The vigilantes clearly knew where to go, whom to target, and which rooms contained which
Starting point is 02:23:26 individuals. That level of operational detail strongly suggested access to intelligence that only an embedded informant could reasonably have provided. McParlane himself, when the incident was later investigated by journalists and by defence attorneys in the subsequent trials, denied any direct role in the raid. He claimed that information he had provided to his superiors had been passed along without his knowledge to parties he did not control, and that the vigilante action had not been authorised by the Pinkerton Agency. Whether this was true, partially true, or a self-serving reconstruction designed to distance the agency from an embarrassing episode is, again, one of those questions that the surviving documents cannot fully settle. What is clear is that the raid on the
Starting point is 02:24:12 O'Donnell House was, in its essential character, an act of extrajudicial violence conducted by masked men operating with apparent impunity, and that it occurred in the context of a broader campaign, in which a private detective agency was working directly for private mining interests to identify and destroy alleged conspirators within the miners' own communities. The trials, when they came, were the most remarkable feature of the entire affair, and they are what made the Molly Maguire prosecutions into a permanent touchstone in the history of American law. Between 1876 and 1879, a series of trials were held in the courthouses of Shulkill and Carbon counties in Pennsylvania, at which approximately 50 men were tried for murders, conspiracies and related crimes
Starting point is 02:24:59 allegedly committed as part of the Molly Maguire conspiracy. The extraordinary feature of these trials, the feature that made them unlike anything else in the contemporary American legal system, was the institutional structure of the prosecutions themselves. The prosecution was not conducted in any meaningful sense by the state of Pennsylvania. The state's role in the proceedings was essentially limited to providing the courtroom, the judge and the executioner at the end. Everything else, in a pattern that had no real precedent and would have no real successes, was handled by the coal companies themselves and by the Pinkerton agency they had hired. The investigation into the alleged crimes had been conducted
Starting point is 02:25:39 by McParland, a private detective in the employ of a private company. The evidence had been collected by McParland and by other agents working for the same company. The prosecution attorneys at most of the trials were private lawyers retained by the coal company. including Franklin Gowan himself, who actually argued some of the cases personally as a special prosecutor. The jurors in several of the trials were drawn from pools that excluded Irish Catholics entirely on the theory that Irish jurors might be sympathetic to the defendants. The evidence presented at trial consisted to an overwhelming extent of McParlane's testimony about conversations he claimed to have overheard and confessions he claimed to have heard the defendants make
Starting point is 02:26:19 during their years together in the Irish Catholic community of the Anthracite region. Twenty of the men who were tried were convicted of capital crimes and sentenced to death by hanging. The executions were carried out at various dates between 1877 and 1879, and they were public events in the communities where they occurred, drawing large crowds and generating extensive newspaper coverage. Ten of the hangings took place on a single day, June 21, 1877, in what was later remembered locally as Black Thursday. The condemned men went to their deaths by most accounts without breaking,
Starting point is 02:26:55 and several of them maintained their innocence from the gallows. Whether they were innocent in any strict sense of that word, or whether they had participated in some degree of the violence that the prosecutions alleged, has been argued about for the better part of a century and a half. The evidence for guilt in individual cases ranged from reasonably strong, based on independent testimony and circumstantial evidence to extremely weak, based almost entirely on McParlane's recollected conversations that he had not recorded contemporaneously
Starting point is 02:27:25 in his reports. The legal scholar who captured the essential strangeness of what had happened in the Pennsylvania Coalfields was a later state court judge named John Lavelle, who, looking back at the trials after several decades had passed, described them with a phrase that has been quoted frequently ever since. He called the Molly Maguire prosecutions a surrender of state sovereignty. The language is stark and it is worth pausing over because it captures something important about what had been allowed to happen.
Starting point is 02:27:53 The state of Pennsylvania, which was supposedly responsible for investigating crimes, prosecuting defendants and imposing penalties, had effectively contracted out those functions to a private corporation. The coal companies had hired the investigators, collected the evidence and prosecuted the cases. The state had provided only the formal trial. trappings of legal procedure, the courtroom and the judge and the gallows. Everything of substance had been handled privately by parties who had a direct financial interest in the outcomes. Whether this was a reasonable response to an extraordinary breakdown of order in a remote industrial region
Starting point is 02:28:28 or a profound violation of the basic principles on which American government was supposed to rest was the question that Judge Lavelle was raising, and it was a question that the American public never fully answered. McParlane himself emerged from the Molly Maguire investigations as the most famous private detective in the country. He testified at the trials, survived numerous assassination threats during and after the proceedings, and eventually continued his career with the agency for several more decades. He would appear again in a later chapter of American Labor history as the lead investigator in the case of Big Bill Hayward and the assassination of former Idaho Governor Frank Steubenberg in 1905, in which his methods drew similar controversy.
Starting point is 02:29:11 He lived until 1919, dying in a Denver hospital at the age of 75, having spent most of his adult life as the most successful undercover operative in the agency's history and one of the most controversial figures in American law enforcement. The broader consequences of the Molly Maguire prosecutions extended far beyond the fates of the 20 men who were hanged. The trials had demonstrated to industrial employers across the United States. states that the combination of a private detective agency, a friendly private press, and a cooperative court system could be used to destroy the leadership of any inconvenient labor movement or workers association, whether that movement was a formal union, a fraternal organization,
Starting point is 02:29:51 or an alleged secret society. The model would be applied over the following two decades to steel workers, garment workers, miners, railroad workers, and every other category of industrial labour that attempted to organise itself into a bargaining position. The Pinkerton Agency, having proved the effectiveness of the approach in the Pennsylvania coal fields, would find itself in enormous demand as the industrial conflicts of the late 19th century spread across the country. The agency's reputation, which had until that point been built on the legitimate investigation of criminal conduct, now began to shift decisively in the public imagination. The Pinkertons were no longer primarily seen as the pursuers of train robbers and counterfeiters.
Starting point is 02:30:33 They were increasingly seen in the immigrant and working-class communities of the Industrial East as the armed enforcers of corporate power against ordinary workers trying to improve their conditions. This perception was not entirely fair because the agency continued to do plenty of legitimate criminal investigation work, but it was not entirely unfair either because the agency had indeed accepted contracts from mining and manufacturing companies that put it in direct opposition to the workers those companies employed, and it had carried out those contracts with the same thoroughness and effectiveness it had previously applied to chasing bank robbers. The seeds of the enormous confrontation that would define the Pinkerton brand for the next century
Starting point is 02:31:13 had been planted in the Pennsylvania coal fields. The model had been established, the techniques had been tested, the legal precedents had been set, and the agency, under the leadership of Alan's sons William and Robert, was preparing to apply those same methods on a much larger scale. in a confrontation with organised labour that would produce in the summer of 1892, one of the most infamous industrial confrontations in American history. The small company town had been the laboratory.
Starting point is 02:31:41 The enormous steel mill was about to become the battleground, and a river in western Pennsylvania, on a summer morning that would change the reputation of the agency forever, was about to witness something that no one involved had quite expected, and that everyone involved would spend the rest of their lives either defending or condemning. The town of Homestead, Pennsylvania, sat on the south bank of the Monongahela River, about seven miles upstream from the point where the Monongahela meets the Allegheny to form the Ohio. In 1892, it was the kind of industrial settlement that the United States was producing by the dozen in the great manufacturing corridor that stretched from the mill towns of Massachusetts
Starting point is 02:32:19 through upstate New York and Pennsylvania and into the iron and coal country of the Appalachians. Homestead existed more or less entirely because of the enormous steelware. works that occupied most of the riverfront, a sprawling complex of blast furnaces, open hearth shops, rolling mills and rail yards that together employed roughly 4,000 men, and produced a significant fraction of the structural steel being used to build American skyscrapers, bridges and railroad cars. The works were owned by Andrew Carnegie, a Scottish immigrant who had arrived in the United States as a teenager in the 1840s, worked his way up through the telegraph and railroad businesses. and by the 1890s had accumulated one of the largest personal fortunes in the world
Starting point is 02:33:03 through his ruthless consolidation of the American steel industry. Carnegie was a complicated figure, even by the standards of the Gilded Age industrialists. He wrote essays about the moral duties of the wealthy. He funded public libraries by the thousand. He spoke in favour of labour unions in the abstract and at a safe distance, and he had built a public reputation as a reformer and philanthropist. He was also, when he set his mind to it, capable of the kind of hard-nosed business conduct that his contemporaries admired and his workers hated,
Starting point is 02:33:34 and he had a particular talent for being somewhere else when the hard-nosed decisions were being implemented. In the summer of 1892, Carnegie was somewhere else. He was specifically in Scotland at Skibeau Castle, a country estate he had purchased in the Highlands, and was in the process of remodelling into a suitable residence for a man of his standing. He had left the management of his American business interests in the hands of his partner and chairman, a man named Henry Clay Frick, who had made his own fortune in the Coke industry, the solid fuel derived from coal, which is essential for steelmaking, and who had joined forces
Starting point is 02:34:09 with Carnegie in a merger that had proven spectacularly profitable for both men. Frick was, by general agreement of everyone who worked with him, or against him, one of the hardest and least sentimental businessmen of his generation. He was cold, organized, relentless, and he possessed what his contemporaries called an iron will, which is the kind of description that sounds flattering until you realise it generally meant the person being described was extraordinarily difficult to reason with on any subject he had made up his mind about.
Starting point is 02:34:41 Frick and Carnegie had decided in the months leading up to the summer of 1892 that the contract then enforced between the homestead works and the amalgamated association of iron and steelworkers needed to be broken. The amalgamated, as it was called, was at that time the strongest craft union in American industry, representing the skilled workers who operated the most technically demanding positions in the steel mills. It had negotiated over the preceding decade a series of contracts that gave its members
Starting point is 02:35:08 reasonably good wages by the standards of industrial labour, and more importantly, a significant degree of workplace control. Skilled steel workers at Homestead had genuine input into how the work was organised, how quickly new machinery was introduced, and how the profits of productivity improvements were shared between workers and owners. From the perspective of the workers, this arrangement was hard won and worth defending. From the perspective of Carnegie and Frick, it was an intolerable constraint on management prerogative and a drag on the company's ability to maximise returns, particularly at a moment when new
Starting point is 02:35:42 steel-making technology was making some of the old-skilled craft positions less essential than they had been. The decision, quietly made and carefully planned, was to provoke a confrontation that would end with the union destroyed. Frick proposed contract terms that he calculated the amalgamated could not accept. He set a deadline that he knew the union would refuse to meet. He prepared during the months of negotiation for the strike or lockout that would inevitably result, and his preparations went considerably beyond what even the most cynical observer might have expected. By early summer, the homestead works had been transformed, on Frick's orders, into something that the local
Starting point is 02:36:20 newspapers began to call, with only slight exaggeration, a fortress. A solid wooden fence approximately 12 feet high had been constructed along the entire perimeter of the plant, topped with strands of barbed wire and pierced at regular intervals by loopholes, which are narrow slits designed to allow a defender to fire a weapon through the wall without exposing himself to return fire. Platforms had been built along the inside of the fence to allow defenders to stand at the loopholes. High-pressure water hoses, capable of of directing streams of boiling water at anyone approaching the fence had been installed at strategic points. Arc lamps had been positioned to illuminate the ground outside the fence at night.
Starting point is 02:37:01 Electrical wires, in some accounts, had been strung along the top of the fence in ways designed to cause injury to anyone attempting to climb it, though the documentation on this particular detail is less reliable than some of the others. The workers themselves, who had watched this construction proceeding over the weeks before the actual confrontation, had given the entire complex a nickname. They called it Fort Frick and the name stuck. The formal break came on June 28, 1892, when Frick locked out the workers who refused to accept the new contract terms.
Starting point is 02:37:33 The distinction between a lockout and a strike is a small but important one. In a strike, the workers collectively refused to work and leave the facility, with the goal of forcing the employer to meet their demands. In a lockout, the employer refuses to let the workers enter, the facility and continues to pay them nothing until they accept the employer's terms. Frick had chosen the lockout because it placed the legal and moral burden of the confrontation on the company, which was happy to bear it rather than on the workers. He had also chosen it
Starting point is 02:38:03 because he intended to bring in replacement workers, non-union men hired from elsewhere, to resume production as quickly as possible and break the solidarity of the locked-out force. The replacement workers, however, could not simply be walked into the plant through a picket line of 4,000 angry steelworkers and their families, they needed protection. They needed specifically an armed force sufficient to secure the perimeter of the works, push back any resistance, and establish physical control of the facility before the replacements were brought in. This was not a function that the local police or the county sheriff's office could realistically provide, because the town of Homestead was populated almost entirely by the families of the workers
Starting point is 02:38:42 who were being locked out, and the local law enforcement personnel were themselves either related to the workers by blood, or sympathetic to them, through decades of shared community life. The state militia could, in theory, have been called upon, but that would have required going through the governor of Pennsylvania and would have generated political complications that Frick did not want. So Frick did what American industrialists of the late 19th century had increasingly learned to do in these situations. He hired the Pinkerton's, a contract was negotiated in secret between the agency, which was by this point being run by Alan's younger son, Robert Pinkerton, with his older brother William handling the Western
Starting point is 02:39:21 office, and Frick personally. The agency agreed to provide 300 armed men, transport them to the homestead works, and deploy them around the facility to secure the perimeter and protect the replacement workers who would be brought in afterward. The fee was substantial. The men were recruited from several of the agency's regional offices with a significant proportion coming from the New York and Chicago offices, where the agency maintained its largest reserves of security personnel. Many of them were not experienced agents in the conventional sense, but rather guards hired on a short-term basis for exactly this kind of deployment, which the agency ran as a separate line of business from its detective work. The plan that Frick and the agency developed was elaborate
Starting point is 02:40:03 and from a tactical standpoint not unreasonable on paper. Transporting 300 armed men by train to homestead would have been noticed immediately by the workers and their sympathizers, who would have mobilized to block their arrival. Walking them through the town from the nearest railroad station would have produced an immediate confrontation that could have ended with a battle in the streets. The solution was to bring them in by water. Two large flat-bottomed barges, typically used for transporting freight on the Ohio and its tributaries, were modified with sleeping quarters, kitchen facilities and firing positions. They were to be towed up the Monongahela River by a steam-tug loaded with the 300 agents
Starting point is 02:40:42 and landed directly at the company's private dock inside the perimeter of the works themselves. The men would disembark, take up defensive positions along the fence, and the plant would be securely in company hands before the locked-out workers fully understood what was happening. The operation commenced on the evening of July 5, 1892. The agents, who had been gathered at various staging points along the Ohio River system over the preceding days,
Starting point is 02:41:08 were loaded onto the two barges at a landing near. Pittsburgh, and the tow began its upstream journey toward Homestead in the late hours of that evening. The men had been given rifles, the type most readily available being the Winchester lever action model that was standard for American civilian security work of the period, and they had been told they were being deployed to protect company property from a mob. They had not, in most cases. Been told that the mob in question consisted of 4,000 steelworkers defending their jobs, nor that those steelworkers had been preparing for exactly this kind of intrusion for several weeks,
Starting point is 02:41:43 nor that the town of Homestead had developed an elaborate warning system to alert the workforce the moment the company attempted to bring in outside forces. The warning system worked. Lookouts posted along the river had spotted the approaching barges hours before they reached Homestead and riders had been dispatched on horseback to alert the town. Steam whistles had been sounded across the works and the surrounding neighbourhoods. By the time the tow reached the road, the company dock at approximately four in the morning of July 6th. Several thousand workers and their family members had already gathered at the riverfront, and more were arriving by the minute.
Starting point is 02:42:17 The barges attempted to land. The workers, armed with whatever weapons they had been able to collect, which ranged from hunting rifles to old Civil War surplus muskets to pistols to clubs, refused to allow the landing. Shots were fired, though which side fired first has been debated ever since, and will never be definitively established, because both sides subsequently claimed the other had initiated the violence. What followed was not, strictly speaking, a battle in the military sense.
Starting point is 02:42:44 It was a 14-hour exchange of fire between several hundred men pinned down on two barges in the middle of a river and several thousand men arrayed along the riverbank with cover available in the form of buildings, fences and the sloping terrain of the riverfront. The tactical situation was catastrophic for the agents on the barges. They could not land because the bank was held. They could not retreat because the steam tug had, in the early confusion, cast off from the barges and fled downstream to avoid taking fire, leaving the barges without propulsion and anchored in place by the current.
Starting point is 02:43:17 They could only shelter behind the walls of the barges themselves, returned fire when targets presented themselves, and hoped that some form of relief would arrive. The workers, meanwhile, had initial difficulty understanding what they were up against, but they learned rapidly. Within a few hours they had produced from various sources in the world, the town, a collection of improvised offensive weapons that transformed the situation from a stalemate into a siege. A small cannon was dragged to the riverbank and fired at the barges, though its aim was
Starting point is 02:43:46 poor and its effects on the armoured barges were limited. Dynamite, which was plentiful in a steel town where it was used for various industrial purposes, was packed into containers and thrown, or floated toward the barges. Oil-soaked rafts were set on fire and pushed out into the current in an attempt to drift them into the barges and burn the agents out. At one point a railroad flat car loaded with burning cotton was rolled down the tracks that ran along the riverbank in an attempt to use it as a projectile against the barges, though the attempt failed when the car derailed before reaching its target. The agents on the barges, who had been contracted for a security deployment and found themselves instead in something resembling a naval engagement, sent increasingly
Starting point is 02:44:28 desperate messages downstream by whatever means they could. Some of their offers, were dead or wounded. Their food and water supplies, which had been calculated for a short occupation rather than a prolonged siege, were running low. The barges had been hit repeatedly by gunfire and by explosives, though the structural damage was limited enough that the boats remained afloat. Several of their men had been killed. Many more had been wounded. The July sun, which rose shortly after the fighting began and remained directly overhead during the middle of the day, had turned the interior of the barges into a kind of oven that was making conditions. steadily worse. Casualty estimates vary among the surviving sources, but a reasonable consensus
Starting point is 02:45:08 suggests that nine of the homestead workers and three of the agents were killed during the exchange, with several dozen wounded on both sides. The workers, who had absorbed the majority of the casualties, were also the ones who controlled the bank and had access to reinforcements and medical care. The agents, who had fewer casualties in absolute terms but were trapped in a much worse tactical position, had no access to medical facilities beyond what they had brought with them, and their situation was deteriorating by the hour, by late afternoon. The agents raised a white flag. The commander of the Pinkerton contingent, a man named Frederick Hinder, attempted to negotiate terms of surrender with the strike committee that had emerged to direct the workers' side of the confrontation.
Starting point is 02:45:50 The terms the workers offered were, under the circumstances, relatively restrained. The agents would be allowed to disembark, would be disarmed, and would be permitted to leave homestead under the protection of the local authorities. The agency's weapons and equipment would be confiscated. No individual agent would be held for criminal prosecution unless specific charges could be substantiated against him. The alternative, the workers made clear, was continued siege, which at that point could only end with the barges being set on fire, and their occupants killed or forced to swim in a river, where riflemen on the bank would have very little difficulty targeting them. The agents accepted. They put down their weapons, came out onto the decks of the barges,
Starting point is 02:46:32 and were allowed to land on the bank in small groups. What followed was the most humiliating moment in the agency's history, and it was documented with considerable thoroughness by the press photographers and journalists who had by this point arrived in homestead from Pittsburgh and further afield. The 300 surrendered agents were marched through the streets of the town, in what amounted to a ritualized walk of shame. The townspeople who had spent the past 14 hours watching friends and family members being shot at from the river formed dense crowds along both sides of the route, and they expressed their feelings in ways that the agents would remember for the rest of their lives. The march through town, which has been described by various witnesses in accounts that generally agree on the essential
Starting point is 02:47:13 features, lasted several hours and covered perhaps a mile and a half from the riverfront to the railroad station, where the agents were eventually entrained for departure. During that walk the surrendered men were jeered at, spat upon, pelted with rocks and garbage, struck with umbrellas and walking sticks, and subjected to the full range of physical and verbal abuse that a town of several thousand angry people can produce when its members have just collectively won a 14-hour battle against an invading force. The women of Homestead, who had not been involved in the firing from the riverbank, but who had spent the day in the town waiting for news were reportedly among the most vocal participants in this final humiliation.
Starting point is 02:47:54 Several agents were seriously injured during the March, with one or two requiring hospitalisation. By the time the survivors were loaded onto trains and sent back toward Pittsburgh, the agency's 300-man force had been reduced, morally, if not literally, to a group of beaten men who wanted nothing more than to be somewhere else. The aftermath of the homestead confrontation was a public relations catastrophe for the agency, for the Carnegie Steel Company and for Frick personally, and it played out across the front pages of every major newspaper in the country, and indeed in much of the international press.
Starting point is 02:48:28 The image that emerged was not the one Frick had hoped for. The workers, who had taken up arms against an invading force landing on their home territory from the river, were portrayed in much of the press as defenders of their community and their livelihoods. The agency, which had attempted to land 300 armed men had a private dock under cover of darkness to break a strike, was portrayed as a kind of private army operating outside any legitimate chain of command. Accountable only to the wealthy industrialist who had paid for it, the Carnegie Company, which had planned and financed the entire operation,
Starting point is 02:49:01 was portrayed as a corporate entity so powerful and so indifferent to the norms of American civic life that it felt entitled to deploy armed men against its own workforce. Carnegie himself, still in Scotland, throughout the confrontation, emerged looking particularly bad. His absence from the decisive moments of his own company's most controversial action appeared to many observers as a deliberate attempt to maintain his reformist public image, while allowing Frick to take the public criticism for the decisions that Carnegie had himself approved in advance. Editorials in newspapers from Boston to San Francisco noted the convenience of his absence and drew obvious conclusions.
Starting point is 02:49:40 The great philanthropist who funded libraries and wrote essays on the moral responsibilities of wealth had, it appeared, also personally authorised the hiring of a private army to break a union, and had then taken care to be thousands of miles away when the inevitable violence occurred. The cognitive dissonance this produced in the public image of Carnegie was one that he never fully recovered from, and his biographers have been forced to wrestle with it ever since. Frick, for his part, was shot a few weeks after the Homestead Confrontation, by a young anarchist named Alexander Birkman, who had travelled to Pittsburgh specifically to assassinate him as a political statement in solidarity with the homestead workers. Frick was badly wounded but survived,
Starting point is 02:50:23 returned to work within a few days, and continued to run the company as if nothing had happened. The assassination attempt, which Frick handled with his characteristic coldness, did nothing to soften his public image or to rehabilitate the agency's reputation. It did, however, introduce into the American political consciousness the specter of political violence emerging from the Labour movement, which would recur in various forms over the following decades, and which the agency would find itself increasingly tasked with investigating. The Homestead Confrontation produced legislative consequences that would permanently reshape the legal environment in which the Pinkerton Agency operated.
Starting point is 02:51:01 In 1893, the United States Congress passed what became known as the Anti-Pinkerton Act, formerly titled as a provision prohibiting the hiring of employees of private detective agencies by the federal government. The law was specific, though its origins were general. It grew directly out of the outrage over the Homestead Battle, and it reflected a widespread congressional consensus that the federal government ought not to be in the business of hiring what amounted to private armies to enforce its laws or protect its property. The law remained on the books, in modified form for the next century and beyond,
Starting point is 02:51:34 and it would occasionally be cited in later disputes about the use of private security contractors in various federal contexts. The states were not far behind. Within a few years of the Homestead battle, 23 state legislatures had passed their own versions of the Anti-Pinkerton Act, restricting in various ways the ability of state and local governments to hire private detective agencies for law enforcement purposes. Some of the laws went further, prohibiting even private employers from hiring out-of-state private security personnel during labour disputes in an attempt to prevent the kind of armed interventions that had characterised the homestead affair. The legal landscape that had allowed Frick to secretly contract for 300 armed men and transport them by barge to his own
Starting point is 02:52:19 factory was, within a decade substantially more restricted, though plenty of loopholes remained and the agency continued to find ways to provide similar services under different structures and legal fictions. The longer-term consequences of homestead for the agency itself were mixed. In the short term, business suffered. Several clients who had been considering hiring the agency for various projects quietly backed away, concerned about the public relations implications of being associated with the Homestead affair. The agency's name, which had for decades been a mark of quality and professionalism,
Starting point is 02:52:55 now carried a distinct taint of corporate violence and anti-worker activity, and this taint would never fully be removed. Recruiting new agents became more difficult because the work was now publicly associated with being hired muscle in labour disputes, rather than with the prestigious detective work that had been the agency's original identity. At the same time, the agency's basic business model
Starting point is 02:53:18 continued to generate enormous revenues. The industrial conflicts of the late 19th and early 20th centuries did not diminish after homestead. They intensified. and industrial employers, despite the new legal restrictions, continued to need the kinds of services the agency provided, whether for actual criminal investigation, for internal corporate security,
Starting point is 02:53:39 or for the more controversial work of infiltrating unions and monitoring workers. The agency adapted, shifted more of its labour-related work into the shadows, and continued to grow through the 1890s and into the new century. Its reputation was compromised, but its client base was substantial, and the fees it could charge for its increasingly specialised services remained high. William and Robert Pinkerton, running the agency their father had built, took the public criticism in stride and quietly began the process of rebranding the agency for a new era. They could not undo homestead, but they could try to shift the company's identity back toward its criminal investigation routes,
Starting point is 02:54:18 emphasize the agency's long history of legitimate detective work, and downplay the labor dispute work that had produced the controversy. Over the following decades, the labour-related operations continued, but they were conducted with less public visibility and under more carefully constructed legal covers, and the agency gradually re-established itself as a large-scale security provider rather than a detective agency in the classical sense. The barge load of armed men floating up the Monongahela River
Starting point is 02:54:46 in the dark hours of a July morning in 1892 had marked, though nobody quite understood it at the time, the end of one era in American industrial relations in the beginning of another. The open use of a large-scale private-armed force against organised workers had proven to be politically unsustainable. The era of the forced landing, the fortified mill, and the company-hired army had ended in a cloud of gunpowder and public outrage. But the underlying conflict between industrial capital and organised labour was not resolved by homestead. It was merely forced into new and less visible channels, where it would continue to be fought with different tools for decades to come, and where the agency would continue to play a significant, if more discreet role for most of the 20th century.
Starting point is 02:55:30 The story of the agency's decline from that point onward would be a story of adaptation rather than catastrophe. The agency would survive Homestead, survive the Anti-Pinkerton Act, survive the various state regulations, and continue to operate and grow through the 20th century. But it would never again be what it had been in the mid-19th century, a respected detective organisation with a sterling reputation and a national, beloved brand. It would become, instead, something more practical and less romantic, a private security and investigation firm with a long history, a famous name, and a complicated legacy that its modern successors would sometimes acknowledge and sometimes quietly try to forget.
Starting point is 02:56:12 The transition from the world of Alan Pinkerton to the World of Pinkerton, Inc., the corporate security contractor, was about to accelerate, and the 20th century was about to demonstrate that even the most famous and most controversial private agency could adapt to almost any new era if it was willing to change its branding, its practices, and eventually even its ownership. The 20th century arrived in the United States with a cluster of structural changes that would, over the course of a few decades, fundamentally reshape the business environment in which the Pinkerton Agency operated. Some of those changes were direct consequences of the public outrage over the events we have been following. Others were unreliable.
Starting point is 02:56:52 developments that happened to coincide with the shifting political mood and amplified its effects. Taken together, they meant that the agency which had dominated American private investigation for the second half of the 19th century was about to find itself sharing a much more crowded field and competing for a much more limited set of legitimate clients than it had ever done before. The most consequential of these structural changes was the creation in 1908 of a small investigative office inside the United States Department of Justice. The office was initially given the uninspiring name of the Bureau of Investigation, a title that suggested the founders were not particularly interested in generating headlines.
Starting point is 02:57:35 Its first director was a man named Stanley Finch, who had been a Justice Department examiner before taking the new job, and its first staff consisted of approximately 34 agents, most of them transferred from other federal agencies. The Bureau's mandate was narrow. It was initially authorized to investigate, anti-trust violations, land fraud, and a handful of other federal offences that had previously been investigated by ad hoc arrangements involving secret service agents borrowed from the Treasury
Starting point is 02:58:02 Department. The Bureau was not, at its founding, particularly impressive by any measure. It had a small budget, limited legal authority, and a mandate that seemed almost deliberately modest. What it did have, however, was the institutional template that Alan Pinkerton had developed over the preceding half century. The men who designed the new federal agency, including Attorney General Charles Bonaparte, who was, in one of those historical oddities that history occasionally produces, the grand nephew of the French Emperor Napoleon Bonaparte, had spent careful time studying how effective private investigation was actually conducted in the United States. They had examined the Pinkerton operational manuals where those could be obtained. They had
Starting point is 02:58:45 interviewed former Pinkerton agents who had moved into government work. They had looked at the agency's organizational structure, its reporting systems, its criminal archives, its training procedures, and its interagency communication protocols. What they borrowed, they borrowed without particular attribution, which is the standard way of these things. What they built, once the borrowing was complete, was essentially a federal agency modelled on the Pinkerton template, scaled up over time to national proportions, and eventually supplied with legal authority that the private agency had never possessed. The Bureau would, under J. Edgar Hoover, beginning in 1994, be renamed the Federal Bureau of Investigation, grow enormously and become the dominant law enforcement organisation in the
Starting point is 02:59:29 United States. This expansion, however fortunate for American Public Safety, was not particularly good news for the Pinkerton Agency. The federal authorities were now doing, at taxpayer expense, the kind of cross-jurisdictional criminal investigation work that had been the private firm's monopoly since the 1850s. Banks, railroads, and express companies that had once hired Pinkerton's because no one else could do the work, now had a federal alternative available and the federal alternative came without a fee. The market for the agency's most prestigious and most profitable services, criminal investigation of serious cases involving interstate dimensions, was shrinking rapidly. The agency responded by moving further into the two areas
Starting point is 03:00:14 where the federal government was not competing with it. The first was ordinary private security, the provision of uniformed guards for industrial facilities, warehouses, banks, and other commercial clients. The second was the labour surveillance work we have already discussed, which remained enormously lucrative, despite the bad publicity and the legal restrictions. Throughout the first three decades of the 20th century,
Starting point is 03:00:37 the agency's revenue mix shifted progressively away from classical detective work and toward a combination of security guarding and anti-union operations, a shift that was largely invisible to the public, but that had significant consequences for the agency's internal culture and professional identity. The labour work reached what can only be called its confessional moment in 1936, during a series of hearings held by the United States Senate's Civil Liberties Subcommittee, chaired by Senator Robert M. LaFolette Jr. of Wisconsin. The Lafellette hearings, as they came to be known,
Starting point is 03:01:11 were an extended investigation into what the Senator and his staff called industrial espionage, the practice by which large industrial employers hired private agencies to infiltrate their own workforces and spy on labour organising activities. The hearings were unprecedented in American history for the depth of their inquiry and the volume of documentary evidence they forced into the public record. Corporate files were subpoenaed, payment records were produced, surveillance reports were examined, and the principal figures of the private detective industry were called to testify under oath about practices that had until that point been conducted almost entirely in secret.
Starting point is 03:01:50 Robert Pinkerton, too, who was the son of William Pinkerton and the grandson of the original Alan, appeared before the subcommittee and delivered testimony that, while legally careful, effectively confirmed the scope of the agency's labour-related operations. He acknowledged, with the reluctant precision of a man who understood, stands that lying under oath would be worse than the truth, that the agency had between 1933 and 1936 been paid approximately $1.75 million by various industrial corporations for labour surveillance services. He acknowledged, under direct questioning, that agents of the firm had been placed inside specific labour unions for the purpose of reporting on their activities
Starting point is 03:02:31 to the paying clients. The numbers he disclosed were in their way astonishing. Fifty-five Pinkerton agents had been embedded inside the United Auto Workers, the union that represented the enormous workforce of the American automobile industry. 17 more had been embedded inside the United Textile Workers. Smaller numbers had penetrated various other labour organisations across the industrial landscape. The most remarkable single revelation to emerge from the hearings was that the agency had, at one point, been engaged in surveilling a senior official of the United States government itself. Specifically, the firm had been hired to follow and report on the activities of the Assistant Secretary of Labor, Edward McGrady,
Starting point is 03:03:11 who'd been considered insufficiently hostile to labour unions by some of the agency's corporate clients. The idea that a private detective agency had accepted money from private corporations to spy on a sitting federal official responsible for labour relations was, even by the standards of 1930s, American industrial corruption, a step too far for much of the senatorial audience. The subcommittee used the revelation and the broadening. a pattern of which it was a part to argue for legislation that would further restrict the use of private labour spies by industrial employers. The resulting legislation combined with the growing strength of the Labour movement under the New Deal and the passage of the National Labor Relations Act
Starting point is 03:03:52 in 1935, which for the first time provided federal legal protection for union organising activities, effectively ended the agency's labour surveillance business as a significant line of work. By the end of the 1930s, the enormous machinery of agent placement, union infiltration, and confidential reporting that the agency had built up over four decades had been dismantled. Some of it was dismantled voluntarily by the firm itself, which could see the legal and political writing on the wall, some of it was dismantled by direct legal action, and some of it simply withered away, as the corporate clients who had once been willing to pay substantial fees for the service concluded that the costs of being caught were no longer worth the benefits of the information.
Starting point is 03:04:35 The decade of the 1940s found the agency adjusting to a significantly reduced operational footprint. The United States entered the Second World War in 1941, and many of the agency's remaining field agents were drawn into military service or into federal intelligence work that had been vastly expanded to meet the demands of the conflict. The firm itself did contract work for various defence industries, providing security at factories producing military equipment, but this work was routine security guarding rather than detective work in any classical sense.
Starting point is 03:05:08 The agency that had once protected presidents and pursued train robbers across two continents was now, in many of its operations, essentially a large provider of uniformed men standing at factory gates checking identification cards. The leadership of the firm passed through several generations during this period, with the direct Pinkerton family involvement gradually diminishing.
Starting point is 03:05:28 Robert Pinkerton, too, who had testified before the La Follette Subcommittee, died in 1967, and with his death the direct line of family management effectively ended, though various Pinkerton descendants would retain advisory roles and shareholdings for some time afterward. Professional managers without family connections took over the day-to-day operations, and their instinct, as professional managers of declining legacy firms usually instinct is, was to focus on what was growing rather than what was shrinking. What was growing through the 1950s and 1960s was the corporate security industry. American businesses were expanding at unprecedented rates, building new offices, factories,
Starting point is 03:06:10 and warehouses across the country, and each of these facilities needed some form of security arrangement. The Pinkerton firm, which had the advantage of a nationally known brand and a long history in the security field, was well positioned to capture a significant share of this growing market. The management refocused the company's efforts accordingly. In 1965, as part of a broader rebranding effort, the word detective was quietly removed from the company name. The firm, which had been legally known as Pinkerton's National Detective Agency, since the 1850s, was renamed simply Pinkertons Incorporated. The change was for anyone who understood the history significant. The detective agency, as a distinct institutional category, was being retired.
Starting point is 03:06:54 What remained was a security company, with a famous historical name but a more prosaic content. temporary function. The transition from detective agency to security corporation proceeded steadily over the following decades, and it proved, from a purely financial standpoint, remarkably successful. The company grew. It acquired other security firms and merged their operations into its own. It expanded geographically, opening offices in Canada, Mexico and various international markets. By the middle of the 1990s, Pinkerton had become one of the largest private security firms in the world, with approximately 50,000 employees across its various divisions and revenues that dwarfed anything the original detective agency had ever generated.
Starting point is 03:07:37 The company had, in effect, reinvented itself as a modern security contractor, using the historical brand to differentiate itself in a market populated by newer and less distinguished competitors. But the reinvention, however successful in financial terms, had gone far enough that the company itself was no longer recognisable as the company itself was no longer recognisable as the reinvention. the firm Alan Pinkerton had founded. The detective work that had defined the original agency had been reduced to a relatively small division inside a much larger organisation whose primary business was guard services, loss prevention and corporate security consulting.
Starting point is 03:08:13 The famous eye logo and the slogan about never sleeping had been retained because they remained commercially valuable, but the operational reality they had once described was gone. The Pinkerton of 1995 was, in its actual. actual daily operations, a very different creature from the Pinkerton of 1865, and the distance between the two had grown steadily larger with every passing year. The final transformation came in 1999, when the company was sold to a Swedish security conglomerate called Securitas A-B for approximately $384 million. Securitas, which had been founded in 1934 in the Swedish coastal city of Helsingborg, and had grown through decades of acquisitions into one of the largest security firms in Europe
Starting point is 03:08:58 had been expanding aggressively into the North American market during the 1990s. The purchase of Pinkerton was, for Securitas, a major strategic move that instantly gave it a significant presence in the United States and a storied brand name that American corporate clients already knew. For the Pinkerton shareholders, the sale provided a substantial return on their investment and relieved them of the ongoing complications of running an independent security firm in an increasingly consolidated industry. For the historical Pinkerton Agency, in any meaningful sense, it was the end of the road. Securitus initially maintained the Pinkerton brand as a separate division within its corporate structure,
Starting point is 03:09:39 operating as Pinkerton Consulting and Investigations, and the brand continued to appear on corporate security services offered to clients who valued the historical association. the unblinking eye, that famous logo we have already encountered, continued to appear on letterhead, marketing materials and websites, though now as one brand among many in a much larger corporate portfolio, rather than as the defining identity of an independent company. The American private security industry had in its own way, completed its consolidation,
Starting point is 03:10:08 and the firm that had essentially invented the industry in the 1850s had ended its independent existence as a subsidiary of a Swedish multinational. The story might have ended there as a fairly standard corporate history of a 19th century American firm that evolved, adapted, and was eventually absorbed into a larger international entity. It did not end there. In 2020, the Pinkerton brand returned to public attention in a way that no one in the long legacy of the agency would have predicted through a series of news reports that revealed the brand was still being used for precisely the kind of work that had made it controversial in the
Starting point is 03:10:43 first place. The reports emerged through a combination of leaked internal documents and investigative journalism, and they concern the online retail giant Amazon. Reporters at the investigative news outlet motherboard, working from leaked Amazon security team documents, revealed that the company had hired Pinkerton operatives to gather intelligence on its own employees at European warehouse facilities, specifically to monitor and report on labor organizing activities that were developing at several of Amazon's enormous fulfillment centres. The Pinkerton agents, working under the circuitous corporate umbrella, but operating under the historical Pinkerton brand name, had been tasked with understanding which employees were involved in union organising efforts, what kinds of
Starting point is 03:11:25 actions were being planned, and how the workforce was responding to various Amazon management initiatives. The techniques described in the leaked documents were, to anyone familiar with the history we have been following, almost eerily consistent with the methods that had been developed more than a century earlier. Agents were being placed inside warehouse workforces undercover identities. Reports were being filed on specific individuals who had been identified as leaders or potential leaders of organising efforts. Intelligence was being provided to the client, in this case Amazon, on the internal dynamics of the workforce in ways designed to allow the client to intervene preemptively in developing labour situations. The documents did not describe any physical violence
Starting point is 03:12:08 or direct confrontation of the kind that had characterised the 19th century confrontations. The work was subtler, more carefully legally bounded, and conducted under much stricter procedural controls than the earlier operations had been. But the essential function, which was the private monitoring of workers by their employer using a specialised intelligence contractor, was recognizably the same function the agency had been performing since the 1870s. The story produced a burst of public attention in the United States and Europe, primarily because of the striking contrast between the ultra-modern nature of the client, Amazon, the largest online retailer in the world, operating some of the most advanced logistics facilities ever built, and the almost antique nature
Starting point is 03:12:52 of the service being provided. Surveillance of Workers by the Pinkerton's, a firm whose brand had been synonymous with exactly this kind of work since the Gilded Age. Commentators noted, with varying degrees of irony, that the March of technological progress had produced. a situation in which 21st century workers sorting packages for next day delivery were being watched by private detectives operating under a brand name that would have been familiar to their great-great-grandparents. The uniforms had changed, the hourly rates had changed, the basic relationship between capital, labour, and the private intelligence contractor that mediated between them had not. Amazon, when the reports were published, took the standard corporate position
Starting point is 03:13:34 that it did not discuss its relationships with security vendors. Securitas similarly declined to comment in detail on the specific contracts at issue. The Pinkerton brand, as managed within Securitas, did not issue a public response beyond generic statements about the professionalism of its operations and its commitment to legal and ethical standards. The story produced some parliamentary questions in several European countries, a few polite exchanges between regulators and the companies involved, and the kind of sustained but ultimately limited public attention that these sorts of revelations usually produce in the current media environment. No legal action of significance followed. The practices described in the leaked documents
Starting point is 03:14:16 appear to have continued in modified form at various Amazon facilities and elsewhere. What this final episode suggests, and what brings our long story to a kind of natural conclusion, is that the basic logic of private workplace surveillance has proven to be astonishingly persistent across the century and a half since Alan Pinkerton first hired James McParland to infiltrate the mining communities of Pennsylvania. The specific techniques have evolved with the available technology. The legal frameworks have shifted, sometimes in favour of workers and sometimes against them. The public's attention has waxed and waned. But the underlying commercial demand for a service that allows large employers to monitor their own workforces
Starting point is 03:14:57 through a specialised intelligence provider has remained remarkably constant. Where that demand exists and where the legal environment permits it, somebody is going to supply the service. Whether the supplier is called the Pinkerton National Detective Agency, or Pinkerton's Incorporated, or Pinkerton Consulting and Investigations under the Securitus Corporate Umbrella, or whatever name the next corporate reorganisation produces, the underlying function endures.
Starting point is 03:15:23 We began this story with a Scottish boy in the smoky industrial fog of Glasgow, watching his father come home from the streets bloodied, and we have followed the threads of his life and his creation across more than 150 years, through wars and assassinations and coal fields and silver canyons and river battles, and corporate boardrooms and warehouse floors. The threads lead finally into a present in which the original agency no longer exists as an independent entity, in which the famous brand has been absorbed into a Swedish multinational, and in which the work of watching workers continues much as it has. has for most of the period we have covered. The Scottish Cooper, who could not have imagined any of
Starting point is 03:16:02 this created, through the accumulated choices of his long career, a shape of institution that has outlasted him by more than a century, that has travelled into corners of the world economy he never would have heard of, and that has done work both legitimate and controversial in roughly equal measure across the long decades since his death. Which is why, in a sense, stories like this one matter. The past does not stay in the past if we keep paying attention to it. The institutions around us did not appear from nowhere. They were built by people with specific ambitions and specific contradictions, and they have travelled forward in time carrying those ambitions and contradictions into new forms that we can recognise if we know what to look
Starting point is 03:16:43 for. The next time you see an unblinking corporate logo designed to suggest eternal vigilance or read about a company hiring a discreet firm to monitor its own employees, you will know where the template came from. You will know about the Scottish. Cooper, and his first raid on a counterfeiting camp, and his first female detective, and his first fortified mill, and his first congressional investigation, and all the rest of the story that got us from there to hear. Thank you for staying with me through this long tale of a private agency that started with one man's attempt to make something honest out of the chaos of the 19th century American frontier, and ended as a multinational subsidiary watching warehouse workers in several
Starting point is 03:17:23 different countries at once. The arc from one to the other is stranger than any fiction, and the parts that are genuinely verifiable are stranger still than the parts that have been invented by later storytellers, which is saying something given how inventive some of the later storytelling has been. Rest easy, dear listener, sleep well and sweet dreams.

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