Legends of the Old West - PINKERTONS Ep. 6 | “Charlie Siringo: The Wild Bunch”

Episode Date: August 27, 2025

In June of 1899, an outlaw gang robs a train outside of Wilcox, Wyoming. The gang is the Wild Bunch led by Butch Cassidy and the Sundance Kid. The Pinkerton agency receives the assignment to stop the gang once and for all, and Charlie Siringo conducts a 4-year manhunt for the elusive thieves. 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 middle of July, 1989, 44-year-old Pinkerton agent Charlie Seringo stepped into James McParland's office and received his next assignment. Seringo assumed he would have to infiltrate another mining union. McParland, Seringo's boss in the Denver office of the Pinkerton, detective agency had been an undercover operative in unions 20 years earlier. For the better part of a decade, the bulk of Seringo's cases involved mining unions. Of all the cases Seringo had undertaken, probably the most dangerous had involved infiltrating a union in the Idaho

panhandle. For 14 months, Seringo lived and worked with the miners around Cordillane. While he sympathized with their plight, he believed their leaders were exploitative and our During the case, he was accused of being a traitor and was nearly lynched. That had been seven years ago. And now, six months before the dawn of the new century, McParland had a big job for Seringo, and it was not another mining case. Instead, Seringo learned he would need to catch the men who recently robbed a train outside Wilcox, Wyoming. In the early morning hours of June 2nd, the Overland Flyer No. 1, a Union Pacific train barreled west through a mighty storm. Around 2.15 a.m., the engineer looked outside and spotted

a red signal lantern waving in the distance. The engineer knew he was approaching a bridge, and he figured the signal was to let him know the bridge had been washed out. He hit the brakes, but no sooner had the train come to a stop than the engineer turned around and discovered he was staring down the barrel of a pistol. A masked man was pointing a gun at his face, and out of the darkness, four more masked men appeared with rifles. They instructed the engineer to unhitch the locomotive and drive on to the bridge. The engineer complied, and the gang of five men moved to the mail car. They demanded that the men inside opened the door, but the men refused. The robbers fired at the door, but the men inside refused to open.

So, the robbers placed dynamite against the door and blew it open. In the mail car, the thieves found little that satisfied them, and they moved down to the express car. They shouted for the man inside to open the door. But the man behind the door, a clerk named Charles Woodcock, refused. Once again, the thieves dug dynamite to the door and blew it open. The thieves found the now concussed Woodcock in a daze. Instead of killing him, they let him out of the train and over to the other clerks.

The robbers rigged the safe in the express car with dynamite and lit the fuse. The explosion was massive, greater than anyone anticipated. It not only blew open the safe, it shredded the door and the roof of the express car. When the smoke and debris cleared, the robbers filled their sacks with banknotes, cash and gold valuables. The hall was valued at around $50,000, today worth nearly $2 million. With their sacks loaded, they hopped onto their horses and disappeared. Word of the robbery quickly spread, and it was one of many in a frustrating pattern. The Pinkerton agency was hired to catch the thieves, and Charlie Seringo was now on the hunt for Butch Cassidy and the Sundance Kid.

From Black Barrel Media, this is Legends of the Old West. I'm your host, Chris Wimmer. In this season, we're focusing on the famous Pinkerton Detective Agency and two of its most famous operatives, James McParland and Charlie Sorringo. This is episode six, Charlie Seringo, Part 3, The Wild Bunch. The June 1899 Wilcox heist was by no means the Wild Bunch's first train robbery, but it was the one that made national headlines. The gang was a loose federation of desperadoes that was formed in large part by Butch Cassidy,

born Robert Parker, sometime in the early 1890s. Cassidy began his criminal career at a young age, first as a cattle rustler, then as a bank robber. As he grew older, he earned a reputation for being. being charming and clever, and he was able to recruit a gang of thieves to help him to expand into train robbery. Among those, the two most famous were Harry Longbaugh, also known as the Sundance Kid, and Harvey Logan, known as Kid Curry. Sundance was a reputed gunfighter, but Kid Curry had the reputation for being a cold-blooded killer, the deadliest man of the wild bunch. Together, the three men oversaw one of the smartest and most successful gangs in the closing days of the

Old West. In the summer of 1890, after robbing a Union Pacific train near Wilcox, Wyoming, they became Charlie Seringo's next assignment. When James McParland gave Seringo the case, he said Seringo wouldn't be working alone. Given the scope of the manhunt and the fact that they were several weeks behind the heist, the agency knew it would need to double the effort. Seringo was given a partner, Billy Sales. Sales was another well-respected Pinkerton operative who had worked with Soringo on a few cases. In 1895, three years after Syringo's Idaho mining case, they worked in Alaska to track down $10,000 worth of stolen gold bullion.

They posed as liquor salesmen, which allowed them to make quick friends and loosen lips. They eventually found the stolen bullion. on a schooner. The two had a harmonious relationship, and Seringo didn't mind having a friend to ride with. Seringo and Sails left Denver and made their way to Salt Lake City. The plan was to buy horses and start riding back along the borders of Colorado and Wyoming. At the time, it was well known that thieves and bandits hid in the nearby maze-like mountains. But when the two detectives made it to Salt Lake City, they met with an old friend named Cyrus Rivers, who told them some interesting developments.

According to Rivers, two of the alleged bandits had been seen in southern Utah, not Colorado or Wyoming. Allegedly, the men rode with 13 horses and were heading for robbers' roost, a hideout tucked away in a Utah canyon. With no other leads, Seringo and Sales bought their horses and rode south. When they made it to the town of Price, Utah, Seringo and Sales checked into a hotel and claimed to be prospectors. But the fact that they were heavily armed raised the eyebrows of Sheriff C.W. Alred. Sheriff Alred was already on edge because he knew outlaws like to hide in his county, and he, like many others, suspected the Wilcox train robbers were using the robbers' roost hideout. Sheriff Al Red had a feeling that the two newcomers weren't prospectors. They were

train robbers, so Alred assembled a small posse and headed to the hotel. Allred's posse greeted Seringo and Sales with loaded rifles and demanded to know why they were really in the area. Seringo and Sales repeated their cover story of being prospectors, and to prove it, they showed the posse their mining equipment. As Sheriff Allred studied Seringo and Sales, he decided they might be telling the truth. He told them that since the Wilcox robbery, any suspicious characters in the area needed to be questioned.

Syringo and Sales understood, and they left town the next morning. Over the next few weeks, Seringo and Sales rode all around southern Utah. In addition to hearing about sightings, the two discovered that some of the stolen bills were now being used in circulation. When one of the bills appeared at a hotel, Seringo asked for a description of the man who had paid with the cash. The description sounded a lot like Harvey Logan, alias Kid Curry. The detectives felt confident that at any moment they would find either Curry or another member of the Wild Bunch.

But as the days ticked by and the journey took them farther south to New Mexico, they began to feel like they weren't making progress. While resting in Lumberton, New Mexico, Seringo and Sails decided they could cover more ground by splitting up. After traversing a thousand miles together by horse and by train, the two parted ways. sales headed back north to Colorado with the hope of finding more stolen money circulating in the area and Seringo stayed in New Mexico to search for new leads This episode is brought to you by Defender With its 626 horsepower twin-turbo V8 engine

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Build it right, build it Rona. Conditions apply, details in store, and more offers at rona.ca. Okay, shut it off. Not long after Seringo and sales separated, Syringo received promising news from an old client named J.M. Archiletta. Seringo knew Archeletta from his first major assignment, when Seringo was sent to help Archeletta County, Colorado, stave off an insurrection. J.M. Archeleta was one of the county commissioners, but he lived in northern New Mexico. He was still a prominent politician in the area, and he told Seringo that a couple of men matching

the descriptions of Kid Curry or his gang were traveling down to Bland, New Mexico. The town was about 180 miles south in the heavily forested mountains outside Santa Fe. Seringo hopped on his horse and began probing the maze of rocky canyons of the Sangre de Cristo and Hems Mountains. But Seringo was chasing ghosts. For weeks, he circled the area and found no clues that led to Kid Curry or his companions in New Mexico. At some point, he got a tip that Curry was in Arkansas. So, Syringo dutifully headed east across the Texas Panhandle in Oklahoma. But when he made it to Arkansas, he learned the outlaw in question was a different Kid Curry.

The Kid Curry in Arkansas used the same nickname but spelled it differently. To make matters more confusing, he sometimes rode with the Kid Curry from the Wild Bun. After that long, frustrating, and fruitless detour, Seringo rode back to New Mexico. When he arrived, he found a telegram waiting for him. It was from his partner, Billy Sales, and Sales had a hot lead. While Saringo was chasing the wrong man, Sales had discovered Kid Curry's true identity. At the time, the Pinkertons did not know that Curry's real name was Harvey Logan.

Salis not only discovered the real name, he learned that Logan had family in Montana. Sales also found out that Logan had a ranch in Montana, which he used for a horse thieving operation. Sales and Seringo would have to divide and conquer. Harvey Logan's brother Lonnie had learned that a Pinkerton was in the area and he fled before Sales could catch him. So, Sails wanted to chase Lonnie while Seringo infiltrated the ranch and tried to catch Harvey. In February 1900, Seringo headed to the ranch, about 160 miles north of Billings. As always, Seringo went straight to the nearest saloon to cultivate relations with the locals.

Shortly after Seringo arrived, he met a man named Jim Thompson. Thompson, as it turned out, helped run the horse ranch that was partially owned by Harvey Logan. Seringo identified himself as Charles Carter, a man who was wanted in Old Mexico. Soringo told Thompson that he was a good cowboy, and when he showed off his skills, Thompson offered him a job at the ranch. Over the next few weeks, Seringo became close with Thompson and helped break and brand horses. As weeks turned to months, Seringo was no closer to catching either of the Logan brothers. Then in June 1900, Seringo learned of a big development.

Lonnie Logan was dead. Apparently at the end of February, at about the same time, time Seringo arrived at the Montana ranch, Pinkerton agents tracked Lonnie to a farmhouse in Missouri. When the agents tried to arrest Lonnie, he opened fire. The agents returned fire and killed Lonnie Logan. Unbeknownst to Seringo at that time, his partner, Billy Sales, was at the shootout. Sales had successfully completed his half of the mission. At the Montana ranch, Jim Thompson said Lonnie's brother, Harvey Logan, knew that the Pinkerton agents who killed Lonnie, had been hired by the Union Pacific Railroad.

Lonnie said Harvey Logan, Kid Curry, was hell-bent on vengeance, and the best way to get even with the Union Pacific was to rob another train. On August 29, 1900, the Wild Bunch, including Butch, Sundance, and Kid Curry, Harvey Logan, held up the Union Pacific No. 3 train outside Tipton, Wyoming. In a strange twist of fate, the gang ran into a familiar face. The crew told the men in the express car to open the door, or they would blow it open. One of the men in the express car was Charles Woodcock, a clerk from the Wilcox train robbery, and he readily opened the door.

The gang quickly robbed the train. There's never been solid confirmation about how much money they stole, but the estimates are usually in the same range as the Wilcox robbery, about $50,000 worth of cash and or gold. When the loot was packed, the gang fled to Colorado. Not long after the tipped-in robbery, Sorringo was called back to Denver. His time at the Montana Ranch hadn't led to much, and it was unlikely that Harvey Logan would return to the ranch so soon after a big robbery.

Seringo learned that the agency received a tip about Logan's movements. An ex-convict claimed to have spoken to the outlawful, known as Kid Curry, and Curry revealed he was heading south. So Syringo packed up and journeyed back to southern Utah. Charlie Seringo spent weeks riding through Southern Utah in search of members of the gang. His traveling companion was a man known as Pegleg. Pegleg claimed to have recently met Kid Curry and Pegleg guided Syringo around the region. They checked possible hiding spots, including the infamous robber's roost, but they found no sign of the bandits.

They did learn that stolen money was being spent in the area, but they couldn't trace it to its source. Eventually, Seringo received instructions from Denver to go to Circleville, Utah, where Butch Cassidy's family lived. The agency hoped that Seringo could learn more about Cassidy himself and maybe discover if the family was in contact. Soringo spent a week with Cassidy's family, but he learned nothing useful. After more weeks of feudal searching, Seringo headed north to Grand Junction, Colorado, where he made a hopeful discovery. He met a man named Jim Foss, who was a friend of the Wild Bunch. From Foss, Saringo discovered an important clue about how the boys evaded capture. They used a complex set of cipher codes when writing messages to each other, and they used a system of so-called

blind post offices in New Mexico, Colorado, Utah, and Wyoming. The blind post offices were similar to what spies today might call dead drops. The gang hid messages in rock crevices or under fake boulders. And while an understanding of the system of communication was nice, it still didn't lead to any of the robbers. Seringo's closest call occurred sometime in late 19, One evening, Seringo sat in a saloon in Rollins, Wyoming. At the time, he was going by Harry Blevins, a name Jim Foss had given him. As Seringo sipped a drink in the saloon, he didn't

know that a man was watching him intently from a backroom hiding spot. That man was Harvey Logan, alias Kid Curry. Seringo eventually left the saloon, having no idea that he was just a few strides away from the man he had been hunting for more than a year. And Seringo wouldn't learn about the near miss for several more years. In the meantime, Seringo chased the wild bunch for an additional two years with no success. He met friends and associates of the gang, but he never got close to the members themselves. By 1903, Charlie Seringo had had enough. In his own estimation, he traveled more than 25,000 miles by horse, rail, stage, and foot. For four years, his sole assignment was to search for the men who robbed the Wilcox train

at 1890, and it was clear he wasn't going to catch them. When Charlie Seringo finally closed the book on the case, he didn't know how right he was. In February, 2001, just a couple months after Seringo's close call with Harvey Logan in Wyoming, Butch and Sundance left the U.S. for South America. Legend has it, the two men died in a hail of bullets during a shootout with Bolivian soldiers. Meanwhile, Harvey Logan bounced around the U.S. and continued to evade law enforcement until June 1904, when he shot himself after a botched train robbery. To the end of Seringo's days, he never believed it was the real Kid Curry who died that day in 1904.

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Is every fabulous item I see from winners? Like that woman over there with the designer jeans. Are those from winners? Ooh, are those beautiful gold earrings? Did she pay full price? Or that leather tote? Or that cashmere sweater? Or those knee-high boots?

That dress, that jacket, those shoes. Is anyone paying full price for anything? Stop wondering. Start winning. Winners Find Fabulous for Less. The Wild Bunch assignment was Charlie Seringo's longest active case, and it ended with an unsatisfactory conclusion. If there was one positive,

Seringo gathered an immense amount of knowledge on ciphers and blind post office drops that the Pinkerton agency was able to use for other cases. But in terms of bringing the robbers to justice, the case was a bust, though Seringo had little time to dwell on the end. outcome. In November 1903, Soringo accepted a case that he called the strangest of his career. A wealthy young man named Edward Wence had recently disappeared in the Cumberland Mountains around the Virginia, Tennessee border. Wence was the son of a prominent wealthy landowner, and the rumor was that Wence had been kidnapped from Virginia and taken to Kentucky to be held for

ransom. Everyone warned Seringo that it was a dangerous case in a dangerous land. That was Hatfield-McCoy country and the home of a dozen other violent feuds. The people in those mountains had been fighting agents of one kind or another for more than a hundred years, and if they felt threatened, they might not think twice about disappearing a nosy detective. Seringo arrived in eastern Kentucky and quickly realized it was not going to be like any other case in his career. He attempted to cultivate favor with the locals using his tried and true Texas cowboy cover, but no one was impressed. In fact, everyone suspected Seringo was a Pinkerton who was looking for Wenz, or a federal agent poking around about illegal alcohol production. A few days in

Eastern Kentucky revealed nothing. So Seringo ventured into Virginia where Wence had been taken. About a month or so into his time in Virginia, Seringo became friendly with a woman named Lottie. In early 1904, she revealed that Edward Wentz was already dead. According to Lottie, Wince's kidnapping had nothing to do with his family's wealth. It was because Wence opposed saloons operating near the coal fields the Wens family owned. Wence, it seemed, didn't like the idea of his coal miners getting liquored up before, during, or after work. A feud broke out between Wentz and the saloon owners, and the saloon owners killed Edward Wentz. A couple months later, Wence's body was found in the woods near Kellyville, Virginia,

and had been made to look like Wence took his own life. He suffered a single gunshot to the chest from a 32-caliber pistol, which was found nearby. Most people believe the scene was staged, but no one was charged with the murder of Edward Wence. A grand jury ruled the death was accidental, and declared the pistol. pistol had misfired. Seringo was certain the case was murder, but in the tight-knit communities of the Appalachian Mountains, he could take the case no further. Seringo returned to Denver and continued to work on various cases out west for the next couple years. But the few months he spent in Kentucky and Virginia made him seriously consider

how long he could keep chasing outlaws. He began to wonder if it was time to turn to in his Pinkerton badge. In the summer of 1907, 52-year-old Charlie Seringo accepted his final assignment. He was tasked with being the bodyguard for a confessed killer named Harry Orchard. Orchard was a minor in Idaho, and two years earlier, he assassinated the former governor of Idaho, Frank Stunenberg. The assassination was linked to ongoing labor disputes between the miners and the mine owners in the Idaho Panhandle, a dispute Seringo was all too familiar with. Seringo had infiltrated the miners' unions in the Cordillane region 15 years earlier in 1892. The case eventually led to the conviction of several union leaders, including

George Pettybone. But Pettybone's 1892 conviction had been overturned. When he was released, he helped create the Western Federation of Miners, with an activist named Bill Haywood, simmering tensions between the WFM and the mine owners boiled over, and eventually Governor Stunenberg was killed. Harry Orchard confessed to the crime, but he said he was acting on orders from Bill Haywood. Now, in the summer of 1907, Orchard was ready to testify against Haywood, and Charlie Seringo was supposed to make sure Orchard lived to take the stand. To defend Bill Haywood and George Pettybone, the Western Federation of Miners employed its go-to attorney, the soon-to-be legendary lawyer Clarence Darrow. Darrow had been making a name for himself as a labor lawyer, and he would continue to do so for a few more years, during which he defended

the McNamara brothers for bombing the L.A. Times building in 1910. After that trial, the unions severed ties with Clarence Darrow, and Darrow turned to criminal law. He became a household name for defending murderers Nathan Leopold and Richard Loeb and defending Tennessee teacher John Scopes in the famous Scopes Monkey Trial. In Idaho, from 1906 to 1908, Clarence Darrow delivered impassioned speeches to juries, and he won acquittals for Bill Haywood and George Pettybone. As it happened, Charlie Soringo's job as a bodyguard for the confessed killer Harry Orchard, wasn't very eventful. But shortly after the trial,

Seringo heard whispers that a lynch mob was forming to kill Clarence Darrow and Bill Haywood. The mob's plan was to intercept them as they waited for the train.

Seringo warned his boss James McParland about the mob, and McParland warned the governor of Idaho. McParland then went to the train station and confronted the mob. McParland managed to talk the angry men out of delivering vigilante justice. Warning McParland about the lynch mob would be the last thing Charlie Seringo did as a Pinkerton.

After Haywood's trial, Sorringo returned to Denver and resigned from service. McParland tried to convince Sorringo to stay as a superintendent at another office, but Seringo declined. Now in his 50s, Syringo couldn't keep up with bandits anymore. His 20-year career as a Pinkerton agent was over. Seringo moved to a ranch in New Mexico with his second wife, Grace, but he quickly realized that life as a rancher was too slow. For a few years, Seringo freelanced for various detective agencies, mostly gathering information related to cattle rustling.

During that period, Seringo decided to write about his experiences as a detective, similar to his previous book about life as a Texas cowboy. In 1910, Soringo wrote, A Pinkerton's Cowboy Detective, a true story of 22 years with the Pinkerton's National Detective Agency. The book promised to be an exciting, firsthand account of life working with the most famous detective agency in the country. But the Pinkertons didn't want their secrets revealed to the public, and they filed an injunction to stop Seringo from releasing the book.

Seringo grudgingly agreed to change some names, and in 1912, he published. a cowboy detective. A few years later, under a cloud of failing health and financial problems, Seringo, like other prominent figures of the Old West era, such as Wyatt Earp, moved to Los Angeles during the early years of the movie business. Charlie Seringo, the cowboy detective, passed away in 1928 and was buried at Englewood Cemetery. The old grounds sit directly across the street from the L.A. Forum, the home of the L.A. L.A. Lakers during the showtime years, and a couple blocks away from the colossal Sofi Stadium, the current home of the L.A. Rams and the L.A. Chargers. Charlie Seringo lies in good company with other legends, like Boxer Sugar Ray Robinson,

musicians Ray Charles, Chet Baker, Edda James, and Ella Fitzgerald, actress Betty Grable, and Father Hunipiro Sarah, the priest who rode with Spanish conquistadors in the 1700s, and established missions throughout California. Next time on Legends of the Old West, it's the second installment of our American Frontier sub-series. The first set of stories covered legendary mountain men Jedediah Smith, Hugh Glass, and Liver-Eating Johnson. This time we go east to tell the stories of Earth,

frontiersman Daniel Boone and Davy Crockett. That's next time 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 of 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. Thank you.