Legends of the Old West - OUTLAWS Ep. 2 | “Black Bart: End of the Road”

Episode Date: March 26, 2025

By the early 1880s, Charley Boles – known as Black Bart – is one of the most prolific stagecoach robbers in the American West. Wells Fargo detectives have been chasing him for years with no luck. But when Charley suffers unexpected resistance during a robbery, he leaves behind key evidence. Detectives finally learn the identity of the gentleman outlaw and bring an end to Black Bart’s legendary career. 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

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for the season. Raise your game to the next level this year with BetMGM, a sports book worth a celly and an official sports betting partner of the National Hockey League. BetMGM.com for terms and conditions. Must be 19 years of age or older to wager. Ontario only. Please play responsibly. If you have any questions or concerns about your gambling or someone close to you, please contact Connex Ontario at 1-866-531-2600 to speak to an advisor free of charge. BetMGM operates pursuant to an operating agreement with iGaming Ontario. Stagecoach drivers dealt with stressful situations regularly. The work was exhausting and there were potential hazards everywhere.

The terrain was often treacherous and the weather was unpredictable. During the earliest decades of heavy westward expansion, the 1850s, 60s, and 70s, Native American war parties were constant threats. By the 1880s, bandits, who were often called highwaymen or road agents, were the chief antagonists. For drivers in Northern California, there had been a rise in holdups over the past five years. Since July 26th, 1875, a man donning a mask and wielding a shotgun had robbed stages across seven counties. Although he was generally

polite and he took the express boxes and mail bags instead of the property of passengers, the bandit who called himself Black Bart was causing major headaches for Wells Fargo and Company. Despite their best efforts, they could not identify or catch the outlaw who himself Black Bart was causing major headaches for Wells Fargo and company. Despite their best efforts, they could not identify or catch the outlaw whose real name was Charlie Bowles. Charlie was a former prospector, farmer, and soldier who had abandoned his wife and four kids in Illinois to try to find gold in Montana. In his final letter to his wife, he said he had been working a successful gold claim,

but then two men, who were somehow associated with Wells Fargo, ruined his operation. After that letter, she never heard from Charlie again. He had moved west to California and become the most infamous stage robber in the state, maybe the entire west. He had hijacked 12 stagecoaches and the money from his robberies funded his fancy lifestyle in San Francisco. There he pretended to be a rich mine owner named Charles Bolton. But to continue to afford the finer things in life he needed to continue robbing stagecoaches. In September 1880, Charlie

left San Francisco and traveled by train and by foot to unfamiliar territory. He arrived in Jackson County, Oregon and staked out a popular stretch of highway. He set up camp near a bend in the road and waited for stages to rumble by. Southbound stages were coming from the prosperous mines that littered southern Oregon, and Charlie believed they may be loaded with gold or cash or both. At about 10 p.m., he spotted a stagecoach nearing his position. Jimmy Smithson was the driver, and the glowing lanterns on the front of his stage cast their

light upon Charlie as he stepped out of the darkness. He walked into the road wearing his typical flower sack mask and holding his typical double-barrel shotgun. Charlie made two demands of the driver, hold up your hands and throw down the mail sacks and the box. Jimmy told Charlie that the box was bolted to the stage, so Charlie handed him a hatchet and told him to get cracking. Jimmy was unable to detach the box, so Charlie told the driver to get off the stage. Charlie climbed up onto the bench and broke out the box. Unfortunately for him, there was little inside to justify the effort. Charlie found $1,400 in a mail pouch, which would be about the equivalent of $43,000 today,

but he was disappointed that the express box didn't contain any golden riches. Charlie jumped down and told Jimmy Smithson to get moving. Two days later, Charlie held up another stagecoach in Oregon. Although the express box was empty, the mail contained $1,300. With the pair of robberies, he had stolen the equivalent of more than $80,000 in today's money. The alarm went up throughout Jackson County, Oregon. Newspapers reported that the notorious operator known as Black Bart had waylaid two coaches in the area. Wells Fargo assembled a posse, which included a Native American tracker. But after following the outlaws' trail for 25 miles,

the posse lost their man. Black Bart had vanished again, but unlike previous years, he wouldn't stay dormant for long. From Black Barrel Media, this is Legends of the Old West. I'm your host, Chris Wimmer, and this season we're telling the stories of infamous outlaws Charlie Bowles, better known as Black Bart, Dirty Dave Rudabaugh, and the Doolin Dalton Gang. This is episode 2, Black Bart, part 2 of 2. End of the road.

After Charlie Bowles robbed a pair of stagecoaches in Jackson County, Oregon, he returned to California where he stayed for the remainder of his criminal career. Although Charlie was an expert bandit, robbing stagecoaches was feast or famine, and there was always a chance that his next robbery could be his last. Charlie returned to the sites of previous holdups because he was familiar with the locations and he knew the avenues of escape. Since he often traveled by foot, it was impressive to understand how quickly a wiry man in his

50s could move. Apparently, he was also unfazed by frigid temperatures because he robbed a stage on November 20, 1880, when the weather was icy and freezing. During the holdup, the driver tossed down the mail bags, but he claimed the express box was too heavy and he couldn't pull it out from under his seat by himself. Cautiously, Charlie stepped onto one of the front wheels of the stage and offered to help lift the box. At that moment, the driver pulled a hatchet from between his feet and swung it at the bandit. The hatchet passed within an inch of Charlie's head.

The robber fell backward off the front wheel and crashed to the ground. The stagecoach raced away, and Charlie Bowles was left with only mailbags and a racing pulse. The cycle of Charlie being flush with cash and then being nearly destitute repeated again in the summer of 1881. The money from the three heists in 1880 had lasted for eight months. Charlie hopped a train and traveled up to the California-Oregon border. He set up camp near a trail to wait for oncoming stage coaches, and this time he planned to try a new tactic. On the night of August 31, an unsuspecting stage rolled into Charlie's ambush site,

and the driver spotted a fire burning by the side of the road. When the driver slowed his team of horses, Charlie confronted the man with his shotgun. The stage wasn't carrying passengers, but it was carrying an express box and nine mailbags. Charlie scored a decent haul and sent the driver on his way. Two months later, in October 1881, Charlie robbed two more stage coaches. He had gone from committing one heist per year, usually in the summer, to committing at least three per year. He was stealing more money, but he was also drawing more attention to his activities.

And at least to some degree, he was encountering stagecoach drivers who were more bold than previous victims. The driver in August had nearly smashed Charlie in the head with a hatchet. After the second robbery in October, the driver drove his stage away from the robbery site as instructed, but then he grabbed his gun, turned his stage around, and hurried back to the spot of the encounter with the intent of killing the bandit.

Charlie had maintained his discipline and fled the area quickly, but the trend would continue over the next two years. Meanwhile, the media attention rose exponentially in 1881. Newspapers like the Sacramento Union regularly relayed information about a ghostly highwayman called Black Bart who held up stagecoaches all over Northern California. There seemed to be no way to predict when or where the bandit would strike, which no doubt delighted newspaper editors

because it ensured they could write more stories. But it continued to frustrate lead detective James Hume. He decided to bolster his team of investigators, and he brought in successful lawmen Joseph Thacker and Charles All to help him catch Black Bart. Unfortunately, none of them were near the village of Dobbins in Yuba County on December 16, 1881. But Charlie's experience that day was also unfortunate. He had ventured into the foothills of the Sierra Nevada mountains in search of a lucrative

prize. Instead, he found exhaustion, hunger, and frustration. When he stopped to stage coach on December 16th, he was tired and irritable. His gentlemanly persona slipped, and he used crass language to convince the driver to throw down the Wells Fargo box and the mailbag. He was also timid, and he tried to keep himself concealed because he noticed that the stage had a lot of passengers who may have been carrying guns. No shots were fired and the stage moved on. But Charlie found no money in the express box and very

little of value in the mailbag. It was the beginning of the low point for the infamous black Bart. You just realized your business needed to hire someone yesterday. How can you find amazing candidates fast? Easy! Just use Indeed. Stop struggling to get your job post seen on other job sites. With Indeed Sponsored Jobs, your post jumps to the top of the page for your relevant candidates,

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along a stage route. He spent Christmas camped beneath a bridge like a troll from a folklore story. Two days after Christmas, Charlie stopped to stage and took its express box and mail. To Charlie's exasperation, the items had little in the way of cash. But Charlie was relieved that the coach had no passengers. Some historians believed that it was during this time that Charlie decided if he was gonna keep robbing stages, he was gonna prioritize holding up coaches that had no passengers. Charlie's luck finally changed when, on January 26, 1882, he held up a stagecoach that carried

two express boxes, three mailbags, and not a single passenger. The bandit now had hundreds of dollars in cash and he could finally take a train to Sacramento or San Francisco where he could enjoy hot food and have a roof over his head. Behind him, Detective James Hume was slowly making progress. Hume arrived at the site of the January 26th robbery and tracked Bowles by foot through the Sacramento Valley. But when Bowles boarded a train, Hume lost the trail. Hume didn't know it at the time, but he was playing the long game. It would take another year and a half for the detective to find some success.

The money Charlie stole on January 26th was enough to sustain him until June. On June 14th, 1882, he robbed his unprecedented 22nd stagecoach. The express box was empty, but he grabbed a little money from the mailbag. After that, he headed deeper into the pine forests of the Sierra Nevada mountains, east of the town of Oroville. He targeted one of the many small towns in the mountains that sprang up around gold strikes. Charlie wanted a big score, and he hoped to steal a gold shipment as it moved down out of the mountains. But Charlie should have known that gold was bound to be more protected than express boxes and mail bags. On July 13th, five miles outside of town, Charlie held up a stagecoach that was laden

with gold. The driver was Hank Helm, and the guard was George Hackett. Hackett was formidable, and he had never lost a gold shipment to a bandit. Charlie didn't know that he faced two men who would not be easily intimidated. He leapt onto the road with his shotgun, but the two men on the rig didn't hesitate. Helm shouted to Hackett, socket to him, and Hackett let fly with his shotgun. The bandits spun around and ran back into the trees.

George Hackett jumped down from the stage and chased the robber, but the outlaw escaped into the pine forest. When Hackett walked back to the waiting stage coach, he noticed the highwayman's bowler hat on the ground. Hackett picked up the hat and saw four small holes in it. There were traces of blood on the inside and strands of grayish-white hair. Some of Hackett's buckshot had struck the bandit, but evidently not enough to do major damage. Hackett and Helm continued

their trip, and Hackett was secure in the knowledge that his streak continued. He still hadn't lost a shipment of gold. And given the newspaper coverage of the prolific robber who wore a flower sack mask and a bowler hat, it was possible that Hackett knew he nearly took down the infamous Black Bart. Charlie worked his way back to San Francisco, and he recuperated from his superficial wounds. He was not a young man, and he took his time before venturing back into the familiar grounds of Shasta County, California. When he held up a stagecoach on September 17th, the driver told him that he was going to get caught one of these days. Charlie responded, Perhaps, but in the meantime, give my regards to J.B. Hume, will you?

Detective Hume received word of the holdup and he raced to the scene. But as usual, he was way too far behind Black Bart. The bandit struck again three months later in Sonoma County. It was robbery number 25 in an eight-year period, and Detective Hume was still no closer to catching his prey. Despite being 54 years old, Charlie Bowles set out to rob more coaches in the spring of 1883. From April to June, he took two stages, but neither gave him the amount of cash he wanted. Detectives Hume and Thacker hurried to the sites of the robberies and confirmed that both were the work of Black Bart. But that knowledge didn't help much. Even though the bandit had experienced a couple close calls, he hadn't made any serious mistakes, and he was still in control of his own destiny.

For the bandit, Black Bart, he was still in search of the elusive big score. Near the end of 1883, Charlie decided to return to the place where his career had started. He traveled to Funk Hill in Calaveras County, and on November 3, he conducted robbery number 28. But number 28 would end far differently from number 1. That day in 1883, a 31-year-old stagecoach driver named Reason McConnell urged his team of horses up Funk Hill. McConnell was a seasoned frontiersman who had battled Native American warriors.

That was why he'd been entrusted with a shipment of gold worth $4,200, which would be worth more than $100,000 today. In addition, he carried just one passenger, 19-year-old Jimmy Rillery, whose mother ran a hotel in the area. Jimmy wanted to go hunting with his.44 caliber Henry rifle, and he hitched a ride with McConnell up in the area. Jimmy wanted to go hunting with his.44 caliber Henry rifle, and he hitched a ride with McConnell up into the hills. Halfway up Funk Hill, Jimmy hopped off the stage to start his hunt. McConnell urged his team onward, and Charlie Bowles prepared to jump out of his hiding spot and stop the stage. McConnell's team sensed Charlie hiding behind a boulder. The lead horses stopped and their

ears leaned forward. As McConnell scanned for a predator, the bandit stepped into the road. Black Bart was wearing his customary flower sack mask, but it was now crowned with a slouch hat instead of a bowler hat. Charlie leveled his shotgun at McConnell, but McConnell wasn't intimidated. He shouted, What in the hell are you looking for? Charlie ordered McConnell to unhitch the horses. McConnell wasn't scared, but it also appears as though he wasn't armed, or at least he didn't have a weapon close at hand. He climbed down and unhitched the horses from the coach,

as instructed. Charlie ordered McConnell to lead the horses up the road and away from the robbery site. When McConnell was gone, Charlie crawled into the coach and began to smash open the express box with a hatchet. For whatever reason, it turned out to be slow work, and the delay would prove costly. While McConnell was leading his horses away, he saw Jimmy Rilary. McConnell told Jimmy about the holdup, and they worked their way back to the scene of the robbery. When they were about 100 yards away, they took cover and saw that the infamous Black Bart was still struggling with the Express box.

It had taken Charlie 30 minutes to break into the box, and when he finally stepped down from the coach with the gold, he spotted McConnell and Jimmy in the distance. McConnell grabbed Jimmy's rifle and fired two shots. Then Jimmy took the rifle and fired more shots. As Charlie dashed into a nearby thicket, a bullet struck him in the hand. He crouched and waited to see if he would be pursued. When McConnell and Jimmy didn't approach, Charlie snatched some of the gold coins out of the stash and stuffed the rest into a hollow tree. Then he made it out of Calaveras County, took a train to Sacramento, and eventually made it back to San Francisco.

He checked into one of his favorite establishments, the Webb House, and nursed his wound. The injury didn't keep him from enjoying the lifestyle he had grown accustomed to, but he didn't know that trouble was brewing on Funk Hill. After the heist, a posse had returned to the scene of the robbery. Detectives James Hume and other lawmen scoured the area and found a wealth of clues. The motherlode was a leather satchel that Charlie had forgotten in his haste. In it were scraps of food, shirt cuffs, a belt, a razor, a set of field glasses, and flower sacks that would be used for future masks.

But the most important item was an old handkerchief. The handkerchief was marked FXO7. The code was a laundry mark. It identified the business that had cleaned the bandits' clothes. With a single old handkerchief, Detective Hume finally had the piece of evidence that would lead him to the identity of Black Bart. We asked actual visitors what they loved about Nova Scotia. They had a lot to say. Nova Scotia is majestic, yet also warm and welcoming. The vineyards, the towns, the rolling hills and the ocean.

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Charles Bolton. Meanwhile, Detective Hume and one of his top associates, Detective Harry Morse, began the hunt for the laundry that was used by the outlaw. The men were convinced that only a laundry in a large city would need to use such a mark. A laundry in a large city would have lots of customers, so logically, the laundry would need to mark the items to make sure the proper item went to the proper person. The mark was like a fingerprint, but it would still be a tough task. There were 91 laundries in San Francisco,

and there was no guarantee that the bandit was in San Francisco. But the detectives had to start somewhere, so they began the methodical process of visiting each laundry. Nine days after the robbery, Detective Morse went to a place called Biggs, California Laundry at 113 Stevenson Street. The owner told him that he recognized the laundry mark, and he said it was assigned to a Mr. C.E. Bolton. The owner further told Morse that Mr. Bolton's clothing was dropped off at a tobacco shop

three blocks away. Detective Morse hurried to the tobacco shop and told the owner that his name was Hamilton. He was trying to track down a Mr. Bolton because he was interested in getting into the mining business. The tobacco shop owner said Mr. Charles E. Bolton, who lived at the Webb House, would be at the shop the next day. Detective Morse returned to the tobacco shop on November 14th, and sure enough, he met Charles Bolton.

Detective Morse kept up his ruse of being a businessman named Hamilton, and the lawman and the bandit had a pleasant, though guarded conversation wherein they both tried to keep their true identities secret. Morse suggested they go to his office to continue the chat. Charlie agreed, and the two men then walked a few blocks down the street. To Charlie's shock, the office belonged to Wells Fargo, and inside was Detective James Hume. Charlie quickly braced for an interrogation. Charlie's false persona, Charles Bolton, was supposed to be a rich mine owner. But when Morse and Hume asked pointed questions about the locations of the mines, Charlie

flubbed his words. Charlie started to sweat as Morse asked more demanding questions. The final nail in Charlie's coffin was when Morse noticed a small cut on Charlie's right hand, which Morse presumed small cut on Charlie's right hand, which Morse presumed was a wound from the last robbery. When Morse asked Charlie how he got hurt, Charlie changed the topic. Charlie probably knew he was doomed when Hume summoned San Francisco Police Captain Appleton Stone into the room.

Stone and another officer joined the two detectives, and they all followed Charlie to the web house. They marched upstairs to Charlie's room, room number 40, and Charlie was indignant as the lawman sifted through his belongings. Hume opened up a Bible, and inside was an inscription to, First Sergeant Charles E. Bowles, 116th, Illinois. Detective Hume accused Charlie of using a fake name, and Charlie responded by trying to give yet another fake name. The lawman disregarded the weak attempt, and then Hume ramped up the pressure. He threatened to place Charlie before a witness who claimed to be able to identify the bandit

despite the fact that Charlie always wore a mask. At that point, Charlie, a tired and aging robber, decided to confess. He confirmed his true identity as Charlie Bowles, and he was the prolific stagecoach robber known as Black Bart who had prowled the back roads of Northern California for eight years. Wells Fargo decided to charge Charlie with only the most recent robbery, likely because the evidence was overwhelming and unimpeachable. It was an open and shut case, and Charlie was convicted and sentenced to six years at

San Quentin Prison. Newspapers loved the story and spread it far and wide. Arguably the greatest stagecoach robber in American history had been caught and convicted. The news spread across the country. Charlie's sister in Reno, Nevada read the news, as did his veteran buddies in Illinois. Last but not least, Charlie's wife, Mary,

who had relocated to Missouri, realized her long-lost husband was not dead. Instead, he was a successful criminal, a gentleman bandit, and a poet whose verses would be mimicked by at least one other outlaw. On November 21, 1883, Charlie Bowles was escorted into San Quentin Prison, which had been built in 1852 and was the most prominent prison on the West Coast. Despite being incarcerated as prisoner number 11046, Charlie did not stop being polite, well-spoken, and amicable.

He didn't cause trouble, and he stayed away from the hardened criminals. He wasn't wild about the hard labor at his advancing age, but he did it nonetheless. He also became a prolific letter-writer, and he wrote to his wife, his children, his friends, and even some of the stagecoach drivers he held up. Charlie was a celebrity prisoner, but when he was given an early release for good behavior on January 21, 1888, he left with little fanfare. For whatever reason, Charlie chose not to reunite with his family. After his release, his life becomes hard to track. Rumor and gossip about the infamous Black Bart was prevalent, but most of the stories

were hard to verify. Some people claimed he traveled to exotic destinations like China, Japan, and Australia. Others said he left the country but stayed closer to home by going to Canada or Mexico. Still others said he spent his remaining years in Northern California. One account suggested Charlie settled in Marysville, in Yuba County, and became a pharmacist. In March 1888, three months after Charlie's release, a guest checked into the Visalia Hotel in Visalia, California, a small town in the Central Valley about halfway between Fresno and Bakersfield.

The man signed the guest book as Mr. Moore. He stayed just one night, and he was never seen again. That is presumed to be the last mostly credible sighting of Charlie Bowles, also known as Black Bart. But the rumor mill exploded to life eight months later when a Wells Fargo stagecoach was robbed by a masked outlaw. On November 14, 1888, the bandit held up the stage and also left behind a brief poem. The lone verse read, So here I've stood while wind and rain have set the trees a-sobbing, And risked my life for that box that wasn't worth the robin."

The robbery stoked concerns that Black Bart was back at it. Detective Hume examined the note and compared it to the two previous poems written by Charlie Bowles. To Hume, the handwriting didn't match. He considered the recent robbery to be the work of a copycat and not the infamous Black Bart. More robberies occurred in the following weeks, and Black Bart was naturally the prime suspect. But descriptions of the new robber were so vague that the criminal could have been anyone. Detective James Hume was confident that Charlie Bowles was no longer an active outlaw.

Graham was confident that Charlie Bowles was no longer an active outlaw. He was probably right, and if so, then the life of Charlie Bowles after March of 1888 remains a mystery to this day. He robbed 28 stagecoaches between 1875 and 1883, and he did so with flair, guile, and he never once fired a shot. No one knows how much money he stole, but he ensured that his name and his alias would live forever. Next time on Legends of the Old West, it's the first of a pair of episodes about an outlaw who seemed to be everywhere in the West.

He was in Dodge City while Wyatt Earp and Bat Masterson were lawmen. He played poker with Doc Holliday in Texas. And most famously, he ran with Billy the Kid after the Lincoln County War. The story of Dirty Dave Rutebaugh begins 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 series was researched and written by Michael Meglish. The producer was Joe Guerra. Original music by Rob Valier. I'm Chris Wimmer. Thanks for listening. Have you ever heard about the 19th century French actress with so many lovers that they formed a lovers union? Or what about the Aboriginal Australian bandit who faked going into labour just to escape the police, which she did escape from them, it was a great plan. How about the French queen who murdered her rival with poison gloves? I'm Anne Foster, host of the Feminist Women's History comedy podcast Vulgar History. Every week I share the saga of a woman from history

whose story you probably didn't already know, and you will never forget after you hear it. Sometimes we re-examine well-known people like Cleopatra or Pocahontas, sharing the truth behind their legends. Sometimes we look at the scandalous women you'll never find in a history textbook. Listen to Vulgar History wherever you get podcasts. And if you're curious, the people I was talking about before, the Australian woman is named Maryanne Bug and the French actress was named Rochelle, no less name, just Rochelle. And the queen who poisoned her rival is Catherine de Medici. I have episodes about all of them.