Legends of the Old West - PINKERTONS Ep. 4 | “Charlie Siringo: Cowboy Detective”

Episode Date: August 13, 2025

Charlie Siringo grows up driving cattle in Texas, Oklahoma, and New Mexico. In the early 1880s, Charlie retires from the cowboy life, writes a book about life on the range, and moves to Chicago. But after the Haymarket Affair, Charlie decides on a career change and becomes an agent for the Pinkerton Detective Agency. Charlie moves to Denver and finds himself tackling political problems in Colorado and infiltrating an outlaw gang in Wyoming. Thanks to our sponsor, HelloFresh! To get started, check out our plan: HelloFresh.com/legends10fm Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial. For more details, visit our website www.blackbarrelmedia.com and check out our social media pages. We’re @OldWestPodcast on Facebook, Instagram and Twitter. On YouTube, subscribe to LEGENDS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage. Learn more about your ad choices. Visit megaphone.fm/adchoices

In the years following the bloody and destructive civil war, the United States experienced an unparalleled period of economic growth. While the South tried to rebuild under the controversial reconstruction acts, the rest of the country flourished. Manufacturing in textiles and steel boomed, while oil, production skyrocketed. Railroads united the country, which sent floods of settlers into the Western territories. But as the economy boomed, a dividing line quickly formed in urban society. Throughout the 1870s and early 1880s, wealth became concentrated in the hands of a few. Andrew Carnegie dominated steel, John D. Rockefeller controlled oil, and J.P. Morgan lorded over Wall Street.

those titans of industry created monopolies that lined their pockets with millions of dollars. But to those who worked for the Titans, the Titans earned another nickname, Robber Barons. By the mid-1880s, as wealth grew for the bosses, laborers demanded wage increases and better working conditions. Before long, a labor movement arose, as strikes and protests hit major cities. And it was only a matter of time before blood. was spilled. On May 1st, 1886, tens of thousands of laborers across Chicago put down their tools for a general strike.

Their demand was simple. They wanted an eight-hour workday. And Chicago wasn't the only city affected. New York, Detroit, Cincinnati, and Milwaukee all saw men walk off the job. In Chicago, on the third day of the strike, unarmed workers gathered in front. of the McCormick Reaper Works for a rally. August Spears, a German immigrant and anarchist, bellowed to the crowd to stand strong and to not give in.

Only if they remained with the union would they win their call for an eight-hour workday. Later that afternoon, the doors to the factory opened and the strikers watched as temporary workers, nicknamed Scabs, and strikebreakers, spilled out. Anger ran through many of the strikers. Someone grabbed a rock and threw it, which led to an all-out brawl. Police officers descended into the melee.

Soon, gunshots rang out. Several strikers were wounded, and between two and six were killed. The following evening, May 4th, a rally was held at Haymarket Square on the west side of Chicago. August Spears and roughly 2,000 strikers and activists gathered together to remember those who died at McCormick Reaper Works the day before. Among those in attendance was the mayor of Chicago, who wanted to make sure the rally didn't escalate into violence. As the rally drew to a close, 180 police officers arrived to disperse the crowd. Suddenly, a thundering boom roared across the square. A bomb had been thrown into the crowd.

Confusion and chaos took hold as police officers opened fire on the crowd, only to be met with bullets coming from some of the strikers. The madness lasted just two minutes, but seven police officers and four civilians died and dozens more were injured. The violence became known as the Haymarket Affair, or the Haymarket Riot. Just a few blocks from the square, a retired cowboy and author named Charles Seringo heard the explosion and the gunshots. When Seringo read about the events the next day, he was convinced he needed to find the person who threw the bomb. He decided to change professions and become an operative for the Pinkerton Detective Agency. From Black Barrel Media, this is Legends of the Old West.

I'm your host, Chris Wimmer, and this season we're focusing on the famous Pinkerton Detective Agency and two of its most famous operatives, James McParland and Charlie Seringo. This is episode four, Charlie Seringo Part 1, Cowboy Detective. Two months after the Haymarket Affair, 31-year-old Charlie Seringo walked into the Pinkerton agency's Chicago office and handed over a letter of recommendation. Later that day, Seringo interviewed with William Pinkerton, the son of the agency's founder. William liked what he saw. More importantly, he liked Seringo's background, which made sense because prior to applying to the agency, Charlie Seringo had lived a completely different life.

Seringo hailed from Madagorda Bay, Texas, just off the Gulf Coast. His father, Antonio Seringo, was an Italian immigrant who aspired to be a rancher. In 1852, Antonio married Bridget White, an Irish immigrant, and later bought a ranch in Madagorda. Antonio had big dreams for himself and his family. He could see right away that Texas was a land of opportunity, especially in the growing cattle industry. Sadly, in 1856, a year after Charlie was born, Antonio Seringo died. Antonio's dream had been to settle down and work a profitable cattle ranch. His son Charlie inherited a love of working with cattle, but not the desire to settle down and become a steady rancher.

From an early age, Charlie showed signs of an inquisitive nature and a yearning for adventure. But as he grew older, he never lost sight of wanting to work with cattle. Seringo got his first chance to become a cowboy when he was 12, driving Texas longhorns alongside Vaccaros. He learned everything about being a cowboy, the land, the cattle, how to lasso, how to speak a little Spanish, and mavericking, that is, the process of branding allegedly stray cattle. It was a life young Seringo loved, but it didn't last very long. A few months after his first experience on the trail, Seringo learned that his mother, Bridget, married a man named William Carrier. The plan was to move from Texas to Michigan, so Seringo's mother sold the ranch, packed their things, and boarded a steamboat to head for the Mississippi River,

which would take the family north to Michigan. But neither the marriage nor the trip lasted long. William Carrier was a drunkard who fell prey to con artists and gamblers. By the time the steamboat journey had reached the area around St. Louis, Carrier had thrown away much of Bridget's money. Supposedly, a drunken carrier got into a fight with a crowd in a small town on the Illinois side of the river and ran off. Charlie Seringo never saw William Carrier again.

With Carrier gone for good, Bridget eventually decided to take her daughter, Charlie's sister, and head to St. Louis. Meanwhile, 13-year-old Charlie Seringo stayed in Illinois for a few more months and worked a series of odd jobs. After not hearing from his family for quite a while, Seringo decided to start making his way back to his home. in Texas. While traveling south, Seringo met a shipping agent named William Myers, and Myers

offered to take Seringo in. Seringo moved in with Myers in New Orleans and attended the widely respected Fisk school. But while Seringo appreciated Myers' hospitality, he couldn't stand the Fisk School, and he often got into fights with the other boys. With each passing day, Seringo learned how to hold his own in a strange land, and earned a reputation as someone not to be messed with. But Seringo couldn't ignore the pull of Texas. Around the time he was 15,

Seringo abruptly left New Orleans and sailed back to Texas. In his hometown of Madagorda, he found work as a cowboy for a cattle baron named Abel, Shanghai Pierce. For the next 15 years, Charlie Seringo worked as a cowboy. He herded tens of thousands of cattle across thousands of miles of territory.

He learned how to track and read the terrain, and he also had run-ins with a few of the Old West's famous citizens. In 1878, he worked as a foreman for the LX ranch in the Texas panhandle north of Amarillo. Supposedly, Soringo came across a group of strangers near the ranch's land. One of those strangers, as it turned out, was Billy the kid. Suringo and Billy seemingly got along, and Soringo allowed Billy and his friends to squat on the ranch for a short time. time. But after Billy became a wanted man, Seringo turned on him. At the end of 1880, Sheriff Pat Garrett and a posse came to the area looking for Billy. Seringo decided to help in the manhunt, and he loaned some men from the ranch to Garrett. A few of the ranch hands were

present when Garrett captured Billy in New Mexico. And at about that time, Syringo was growing tired of the cowboy life. In the early 1880s, he met and married Mamie Lloyd. and called it quits as a cowboy. During retirement, he got the idea to write a memoir about his cowboy days. In 1885, he published the first edition of A Texas Cowboy. At the time of its publication, there weren't many firsthand accounts of life on the range, and the book became a minor hit. Realizing he might have talent as a writer,

Seringo moved his family to Chicago in the early spring of 1886. Soringo planned on expanding the book for a second edition. But no sooner had he arrived in the windy city, then violence caused him to change his career path. It didn't take long for Seringo to see that Chicago was a pot ready to boil. Seringo recognized that tensions were high between the workers and the bosses. So when he and Mamy went to bed on the evening of May 4th, He expected the rally in Haymarket Square to turn violent, but he didn't expect the bomb or

the gunfire. The day before, on May 3rd, striking workers led by August Spears held a rally outside of McCormick Reaper Works, a company which manufactured harvesting equipment. The peaceful demonstration turned violent when strike breakers arrived and laborers began throwing rocks at them. Police entered the fray, which resulted in the death of several men and many more wounded. The next night, on May 4th, a rally was held at Haymarket Square to honor the fallen from the previous day. 180 police officers arrived to disperse the crowd of 2,000. As the men and women left, someone threw a bomb into the crowd. The explosion caused police and some armed strikers to open fire. When the smoke cleared, at least 10 people were dead and dozens more

were wounded. A few blocks away, Charlie Seringo awoke to the sound of the explosion and the ensuing gunfire. He reached for his pearl-handled colt revolver to join the fight, but Mamie stopped him. The next morning, Soringo learned new details of the deadly events in Haymarket Square, and he decided to become a detective to find the man who threw the bomb. The Pinkerton Detective Agency's longtime headquarters was in Chicago. On June 29th, Seringo walked into a local bank that he was acquainted with and asked the banker for a letter of recommendation. The banker obliged, and with the letter in hand, Seringo walked over to the Pinkerton office and asked to see William Pinkerton, the eldest son

of the agency's founder. But as a newcomer, Seringo couldn't. see William Pinkerton right away. Seringo's letter of recommendation earned him a meeting with Captain Mike Farley. According to Seringo, Captain Farley put him through the test, though unfortunately Seringo never explained the so-called test. Whatever it was, Soringo passed with flying colors and then interviewed with William Pinkerton. Pinkerton liked Seringo, especially Seringo's background as a cowboy. Pinkerton had spent some time in the West while chasing various train robbers during the 1870s, and he liked the idea of a home-grown cowboy as a detective. Pinkerton asked Seringo for more references, and Seringo gave him a few names, including Sheriff Pat Garrett.

In short order, Charlie Seringo was hired by the Pinkerton Detective Agency. Seringo desperately wanted to bring the Haymarket bomber to justice. But by the time he was hired by the agency, eight alleged conspirators were already arrested. and on trial. So Seringo's first job as a detective was to keep an eye out for potential jury bribes. Throughout the summer and early fall, Seringo tailed jury members with the hope of seeing money exchange hands, but he saw no evidence of jury tampering. At the end of the trial, the eight defendants, including August Spears, were found guilty of accessory to murder. Five defendants, including Spears, were sentenced to hang. Two were sentenced to life.

in prison, and one was given 15 years. Though to this day, no one knows who actually threw the bomb in Haymarket Square. And Charlie Sorringo would never get the chance to find out. Shortly after the trial, Sorringo was reassigned to the brand-new office in Denver. William Pinkerton needed a cowboy detective, and Seringo fit the bill. So in October 1886, Charlie and Mamie packed up and headed to Chicago. While briefly working in Chicago, Soringo learned how to be a city detective, which involved a lot of shadowing people.

But as a cowboy detective, he knew he'd be infiltrating gangs in rugged landscape. As he started to reacclimate to life in the West, he quickly discovered the most irritating aspect of his transfer to Denver. His supervisor, Charles Eames, had turned the Denver office into nothing more than an extortion racket. Soringo refused to participate in the corruption. He didn't hide his disdain, and he would be forced to endure Charles Eames for two long years before a change was made.

Six months after Seringo's transfer, he received his first major assignment, one which would gratefully take him away from Denver and Charles Eames. There was trouble in Pagosa Springs, Colorado, along the border of Colorado and New Mexico. Pagosa Springs was in Archoleta County. Pagosa Springs, and at the time, the county had an unusual dynamic. Most of the commissioners who ran the county didn't live in Colorado. The majority, including the Archeletta Brothers, lived several miles south in New Mexico. The Archeletta brothers were wealthy sheep ranchers who held the most power in the county, and they didn't always acquire that power through legitimate means.

The Archeletta Brothers were known to buy a left, or to send their sheep herders to town on election day to stack the vote. In early 1887, Archeletta County held an election for various positions. To no one's surprise, the Archeletta brothers, as well as other corrupt commissioners, one. The county had a rule which required all five commissioners to go to Pagosa Springs within 60 days in order to accept and keep their positions. But by that time, the rule didn't really matter. the people of Archeletta County were fed up with the commissioners, and they decided to rebel.

The insurgents drove the commissioners out of Pagosa Springs. They burned down a commissioner's house and forced another to resign his post under the threat of a bullet to his head. Before long, anarchy took hold of Archeletta County, and the commissioners hired the Pinkerton agency to help put down the rebellion. The Pinkerton sent Charlie Seringo. Soringo traveled down to Pagosa Springs under the name Charlie Anderson. His cover was that he was a wanted man from Texas who had killed three Mexicans. Seringo's contact was a woman named Mrs. Skace. Mrs. Skase was the wife of a county commissioner who had been run out of town.

Though Commissioner Skace was gone, his family was allowed to stay. Shortly after arriving, Seringo rode to the ranch of a rebellion member known as Gordon G. Using his fake backstory, Seringo was easily able to convince Gordon G that he was a ruffian and a hired gun looking for work. Gordon G. introduced Soringo to the rebellion's leader, E.M. Taylor. Taylor was desperate for help, and he welcomed Seringo with open arms. Over the next few days, Seringo learned that the rebels and the commissioners had gathered on opposable. sides of the San Juan River which ran through town. In total, the rebels were 75 strong, while the commissioners had an army of around 60. But neither side engaged in battle because the rebels had barricaded the bridge across the river. One night, Seringo discovered that the rebels

were planning a surprise attack. The plan was to sneak across the bridge in the early morning hours and start a fire where the commissioners slept. While the commissioners reacted to the blaze, The rebels would open fire with weapons. Seringo knew he couldn't let that happen. Hours before the attack, Seringo snuck across the river and warned the commissioners. Some of the commissioners panicked and fled. Word of the fleeing commissioners made its way to the rebels,

and there was talk of a traitor in their ranks who had revealed their plan to the enemy. Some wondered if Mrs. Skase was the culprit, and they stationed men outside her house to watch her. Seringo knew the house was being watched, but for whatever reason, he decided he needed to leave messages in the home later that same night. His secret routine for communication was to leave messages behind a painting in her house. That night, while the rebels were having a dance, Seringo managed to sneak around the back of the house and slip inside. After leaving his message,

Seringo returned to the dance. When Seringo got back to the dance, he was surrounded. by angry rebels. His absence had been noticed, and allegedly someone saw Seringo near Mrs. Scace's house. Many of the rebels were now convinced that Charlie Seringo was the traitor, and they were ready to hang him. Seringo knew he wouldn't survive if he pulled his gun, so there was only one option. Deny, deny, deny. In a rage, Seringo demanded to know who claimed to have seen him. A man stepped forward, and Seringo yelled at him. Seringo's performance was so convincing that the accuser retracted his statements. Charlie Seringo lived to see another day, but he was on thin ice.

The two sides continued their standoff at the bridge, but after days of a stalemate, the rebels decided to compromise. They proposed that they were willing to share power with the commissioners, and the commissioners agreed to the proposal. But it was also a ploy. As soon as the commissioners felt safe, they arrested 16 rebels and had them indicted by a grand jury for burning property and expelling city officials from town.

The indictments all came from Charlie Seringo's testimony. He accomplished his mission and restored order on behalf of the county commissioners. And with that, he rode back to Denver for the next job. Newspapers claimed a man named Bill McCoy was a Texas desperado of the worst kind. In January, 1887, McCoy was in a rage when he barged into a saloon in Lusk, Wyoming. The night before, McCoy had gotten into a fight at a dance, and now McCoy wanted to settle the score.

Deputy Sheriff Charles Gunn intervened and tried to de-escalate the situation, but McCoy's temper could not be cooled. He shot Deputy Gunn twice, once in the stomach and once in the head. McCoy went into hiding for about a month. And then for reasons that have only been described as foolishness, he decided to return to Lusk. While eating at a restaurant, a small group of citizens jumped McCoy and arrested him. McCoy was handed over to lawmen

and transported to a jail in Cheyenne. For the next six months, McCoy quietly plotted his escape. He enlisted friends on the outside as well as other cellmates, and in August 1887, he made an unsuccessful attempt to break free. Two months later, at the start of October, McCoy cut a hole in the roof of his cell and slipped out into the Wyoming night. He was a fugitive on the run,

and Charlie Sorringo was sent to Wyoming to find him. Seringo arrived in Cheyenne and sat down with District Attorney Coulter Scholl. Skull explained the events leading up to McCoy's escape, but also gave Seringo the name of an accomplice. Skoll told Seringo that the night McCoy escaped, a man named Tom Hall was waiting for McCoy with an extra horse. It was believed that the two made their way to a ranch along the Laramie River, which Tom Hall operated. Scull warned Seringo that the place was heavily guarded by wanted Texas desperadoes. In fact, another detective agency had recently said, sent three men to the ranch, and they had been lucky to escape with their lives.

After gathering the information, Seringo saddled up and started toward the ranch. Along the way, he paused at the Roundup No. 5 saloon. With a drink in hand, Seringo became acquainted with the saloon's owners, an older couple with the last name Howard. Over the next few hours, Seringo drank with the Howard's. He claimed he was from Texas, and he was on the run. Seringo told Mr. Howard that he was on his way to nearby Fort Douglas, and he would feel more comfortable if he could spend the night somewhere in the safety of his fellow Texans. Mr. Howard knew that Soringo was referring to Tom Hall's ranch and warned him to stay away.

The man holed up there would kill a stranger on site, Texan or no Texan. But Seringo wasn't scared. If anything, he was satisfied to know that Tom Hall and maybe Bill McCool, was still at the ranch. So he bought a bottle of whiskey from Mr. Howard and rode toward the ranch. As Seringo trotted along, he devised a plan to ingratiate himself with the desperadoes. He'd fake a broken leg. Near the ranch, Soringo hopped off his horse, tore his jeans, and scratched his leg and knee to make them look injured. Luckily, an old bullet wound would help sell the deception. Then Seringo got back on his horse and tied his boot in a way

that made it look like it was dangling. Not long after creating the ruse, Soringo spotted a few cabins in the distance. As he approached, a dozen armed men filed out of the cabins. They surrounded the newcomer on horseback, and then a tall, lanky man stepped forward and said, What in the hell are you doing here? The tall lanky man was Tom Hall,

and now Charlie Seringo had to pray he was a good liar. Seringo said his name was Henderson and that he had a broken leg. Instantly, Hall's gruff, intimidating attitude changed. He and his men helped Soringo off the horse and carried him into a cabin. Hall inspected Seringo's knee and informed him that it was only sprained. While huddled around a fire, Seringo recognized a man from his childhood in Texas, a guy named Jim McChesney. Seringo feared that McChesney would also recognize him,

and Soringo tried to get ahead of it. He asked McChesney about a girl they both knew, which confused McChesney. It was clear that McChesney did not recognize Charlie Seringo. McChesney, like the others, believed Seringo was a cowboy outlaw who called himself Henderson. As Seringo and McChesney talked, Seringo insinuated that he was a man from their

passed, who had killed a family back in 1872. McChesney bought the lie, that Seringo was a killer from Texas, whose name was Henderson. That evening, Seringo was given Hall's room to rest. Unbeknownst to him, Hall and the rest of the men quietly debated what to do with Seringo. Three of the men feared Seringo was a detective and wanted to hang him. But McChesney vouched for Seringo, and Seringo was spared the noose. Soringo would only learn a few days later how close he came to being killed, but by that time, he was well on his way to earning the trust of the other men. In the weeks following their initial meeting,

Seringo continued to play up his bum leg, and he slowly won the confidence of the gang. Eventually, talk around the campfire turned to Seringo's target, Bill McCoy. Unfortunately, for Seringo's target, Bill McCoy. Bill McCoy was nowhere near Wyoming. In fact, he likely wasn't even in the United States. Tom Hall said that after McCoy escaped jail, McCoy headed east to New Orleans. From there, he was going to sail south to Buenos Aires, Argentina, and join a gang of Texas outlaws. Soringo also discovered that he actually knew McCoy from his cowboy days in Texas,

but at the time, McCoy had been using a different name. Despite the development, Soringo knew there was a chance that McCoy might still be in the country. Soringo needed to get a message to his bosses as quickly as possible, but he couldn't sneak off without raising suspicions, so he waited. Luckily, the gang wanted to have a little fun, and they all rode out to a gambling hall near Fort Laramie. While the gang drank and danced, Soringo saw an opportunity to slip away. He found a hotel and wrote a message to the Denver office

which advises the agency to send a posse to New Orleans. Maybe they could catch McCoy before he sailed out of the country. Seringo remained with Hall and the gang for at least a few more weeks, drinking and getting to know their various misdeeds. But as time passed, Seringo realized he was never going to catch McCoy in Wyoming. And the fact that he hadn't received secret correspondence out of New Orleans solidified the idea that McCoy successfully fled to South America. But all was not lost.

Seringo had gained enough information on Tom Hall, Jim McChesney, and the others to make a solid case against them. One night, while the others were asleep, Seringo sneaked away and sent a message to law enforcement in Cheyenne. The next morning, a posse arrived and arrested Tom Hall and the gang. Realizing that Seringo wasn't around, Hall allegedly said, said, that damned Henderson is at the bottom of this. Seringo did eventually testify to a grand jury about the men he helped arrest, but he didn't like it. Seringo became fond of Hall and McChesney, and he felt guilty about turning them in. He soon realized that attachment was a real danger of undercover work. If there was any consolation for Seringo, unknown legal technicalities

caused the case to collapse, and Tom Hall, Jim McChayette. Chesney and the others walked free. Charlie Seringo returned to Denver and awaited his next assignment. Eventually, he would come to learn that Bill McCoy did make it to South America and rode with a new gang. Such was the life of a detective. You win some, you lose some, especially in a region as expansive as the American West.

Next time, on Legends of the Old West, famed Pinkerton detective James McParlin takes over the Denver office and starts sending Charlie Seringo on assignments that require him to infiltrate mining unions. Those assignments would put him in danger, but they would also cause him to question his work. It was one thing to hunt down bombers and gunmen and thieves, but it was a very different thing to work against miners who just wanted to make a decent living. That's next week on Legends of the Old West. Members of our Black Barrel Plus program don't have to wait week to week to receive new episodes.

They receive the entire season to binge all at once with no commercials. And they also receive exclusive bonus episodes. Sign up now through the link in the show notes or on our website, blackbarrelmedia.com. Memberships are just $5 per month. This episode was researched, written, and produced by Joe Gera. Original music by Rob Valier. I'm Chris Wimmer. Thanks for listening.