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In the middle of July 1899, 44 year old Pinkerton agent Charlie Siringo stepped into James McParlin's office and received his next assignment. Siringo assumed he would have to infiltrate another mining union. McParland, Siringo'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 Siringo's cases involved mining unions. Of all the cases Siringo had undertaken, probably the most dangerous had involved infiltrating a union in the Idaho Panhandle. For 14 months, Siringo lived and worked with the miners around Coeur d' Alene. While he sympathized with their plight, he believed their leaders were exploitative anarchists.
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During the case, he was accused of.
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Being a traitor and was nearly lynched.
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That had been seven years ago.
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And now, six months before the dawn of the new century, McParland had a.
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Big job for Siringo, and it was not another mining case. Instead, Siringo learned he would need to catch the men who recently robbed a train outside Wilcox, Wyoming.
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In the early morning hours of June 2, the Overland Flyer number one, a Union Pacific train, barreled west through a mighty storm. Around 2:15am 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 onto the bridge. The engineer complied and the gang of five men moved to the mail car. They demanded that the men inside open 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.
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They shouted for the man inside to.
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Open the door, but the man behind.
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The door, a clerk named Charles Woodcock, refused. Once again, the thieves stuck dynamite to.
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The door and blew it open.
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The thieves found the now concussed Woodcock in a daze. Instead of killing him, they led him out of the train and over to the other clerks.
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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, but 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 haul was valued at around $50,000 today, worth nearly 2 million. With their sacks loaded, they hopped onto.
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Their horses and disappeared.
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Word of the robbery quickly spread, and.
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It was one of many in a frustrating pattern. The Pinkerton Agency was hired to catch.
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The thieves and Charlie Siringo was now.
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On the hunt for Butch Cassidy and the Sundance Kid.
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From Black Barrel Media, this is Legends of the Old West.
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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 Siringo. This is episode six, Charlie Siringo part three.
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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 desperados that was formed in large part by Butch Cassidy, born Robert Parker sometime in the early 1890s.
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Cassidy began his criminal career at a young age, first as a cattle rustler.
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Then as a bank robber.
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As he grew older, he earned a reputation for 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.
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Cold blooded killer, the deadliest man of the Wild Bunch.
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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 1899, after robbing a Union Pacific train near Wilcox, Wyoming, they became Charlie Siringo's next assignment.
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When James McParland gave Siringo the case, he said Siringo 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. Siringo was given a partner. Billy Sales Foreign 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 and on a schooner. The two had a harmonious relationship and Siringo didn't mind having a friend to ride with. Siringo and Sales 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, Siringo and Sales bought their horses and rode south. When they made it to the town of Price, Utah, Siringo 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. allred. Sheriff Allred was already on edge because he knew outlaws liked to hide in his county. And he, like many others, suspected the Wilcox train robbers were using the Robbers Roost hideout. Sheriff Allred had a feeling that the two newcomers weren't prospectors. They were train robbers. So Allred assembled a small posse and headed to the hotel. Allred's posse greeted Siringo and Sayles with loaded rifles and demanded to know why they were really in the area. Siringo and Sayles repeated their cover story of being prospectors, and to prove it, they showed the posse their mining equipment. As Sheriff Allred studied Siringo 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. Siringo and Sayles understood, and they left town the next morning. Over the next few weeks, Siringo and Sayles 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, Siringo 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 far, farther south to New Mexico, they began to feel like they weren't making progress. While resting in Lumberton, New Mexico, Siringo and Sales decided they could cover more ground by splitting up. After traversing a thousand miles together by horse and by train, the two parted ways. Sayles headed back north to Colorado with the hope of finding more stolen money circulating in the area. And Siringo stayed in New Mexico to search for new leads.
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Not long after Siringo and Sales separated.
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Siringo received promising news from an old client named J.M.
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Archuleta. Siringo knew Archuleta from his first major.
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Assignment, when Siringo was sent to help Archuleta County, Colorado stave off an insurrection.
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JM Archuleta was one of the county commissioners, but he lived in northern New Mexico.
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He was still a prominent politician in.
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The area, and he told Siringo that a couple of men matching the descriptions.
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Of Kid Curry or his gang were.
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Traveling down to bland New Mexico. The town was about 180 miles south in the heavily forested mountains outside Santa Fe.
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Siringo hopped on his horse and began probing the maze of rocky canyons of.
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The Sangre de Cristo and Jemez Mountains.
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But Siringo 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 Siringo dutifully headed east across the.
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Texas Panhandle in Oklahoma. But when he made it to Arkansas.
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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 Bunch.
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After that long, frustrating and fruitless detour, Siringo rode back to New Mexico. When he arrived, he found a telegram waiting for him. It was from his partner, Billy Sayles, and Sales had a hot lead. While Siringo was chasing the wrong man.
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Sayles had discovered Kid Curry's true identity. At the time, the Pinkertons did not.
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Know that Curry's real name was Harvey Logan. Sayles 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 in Siringo 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 Sayles wanted to chase Lonnie while Siringo infiltrated the ranch and tried to catch Harvey. In February 1900, Siringo headed to the ranch about 160 miles north of Billings. As always, Siringo went straight to the nearest saloon to cultivate relations with the locals. Shortly after Siringo 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. Siringo identified himself as Charles Carter, a man who was wanted in Old Mexico. Siringo 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, Siringo became close with Thompson and helped break and brand horses. As weeks turned to months, Siringo was no closer to catching either of the Logan brothers. Then, in June 1900, Siringo learned of a big development. Lonnie Logan was dead, apparently at the end of February. At about the same time, Siringo 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 Siringo, at that time, his partner Billy Sayles was at the shootout. Sayles had successfully completed his half of the mission at the Montana ranch. Jim Thompson said Lonnie's brother Harvey Logan.
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Knew that the Pinkerton agents who killed.
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Lonnie had been hired by the Union Pacific Railroad. Lonnie said Harvey Logan, Kid Curry, was hell bent on vengeance.
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And the best way to get even with the Union Pacific was to rob another train.
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On August 29, 1900, the Wild Bunch.
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Including Butch Sundance and Kid Curry, Harvey Logan held up the Union Pacific number.
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Three train outside Tipton, Wyoming.
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In a strange twist of fate, the.
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Gang ran into a familiar face.
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The crew told the men in the.
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Express car to open the door or they would blow it open.
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One of the men in the express.
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Car was Charles Woodcock, a clerk from the Wilcox train robbery, and he readily opened the door.
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The gang quickly robbed the train.
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There's never been solid confirmation about how.
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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.
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When the loot was packed, the gang fled to Colorado. Not long after the Tipton robbery, Siringo 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. Siringo learned that the agency received a tip about Logan's movements. An ex convict claimed to have spoken to the outlaw known as Kid Curry.
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And Curry revealed he was heading south.
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So Siringo packed up and journeyed back to southern Utah. Charlie Siringo spent weeks riding through southern.
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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 Siringo around the region. They checked possible hiding spots, including the infamous Robbers 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, Siringo received instructions from Denver to go to Circleville, Utah, where Butch Cassidy's family lived. The agency hoped that Siringo could learn more about Cassidy himself and maybe discover.
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If the family was in contact. Siringo spent a week with Cassidy's family, but he learned nothing useful. After more weeks of futile searching, Siringo 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.
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From Foss, Siringo discovered an important clue about how the boys evaded capture. They used a complex set of cipher.
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Codes when writing messages to each other.
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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.
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Or under fake boulders.
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And while an understanding of the system of communication was nice, it still didn't lead to any of the robbers.
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Siringo's closest call occurred sometime in late 1900. One evening, Siringo sat in a saloon in Rawlins, Wyoming.
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At the time, he was going by.
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Harry Blevins, a name Jim Foss had given him.
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As Siringo sipped a drink in the saloon, he didn't know that a man.
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Was watching him intently from a backroom hiding spot. That man was Harvey Logan, alias Kid Curry. Siringo eventually left the saloon having no.
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Idea that he was just a few strides away from the man. He had been hunting for more than a year and Siringo wouldn't learn about.
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The near miss for several more years.
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In the meantime, Siringo 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.
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By 1903, Charlie Siringo had had enough.
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In his own estimation, he traveled more.
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Than 25,000 miles by horse, rail, stage and foot for four years.
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His sole assignment was to search for.
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The men who robbed the Wilcox train.
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In 1899, and it was clear he.
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Wasn'T going to catch them. When Charlie Siringo finally closed the book on the case, he didn't know how right he was. In February 1901, just a couple months after Siringo's close call with Harvey Logan in Wyoming, Butch and Sundance left the US 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 US.
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And continued to evade law enforcement until June 1904, when he shot himself after.
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A botched train robbery. To the end of Siringo's days, he never believed it was the real Kid Curry who died that day in 1904.
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The Wild Bunch assignment was Charlie Siringo's longest active case, and it.
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Ended with an unsatisfactory conclusion.
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If there was one positive, Siringo gathered.
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An immense amount of knowledge on ciphers and and blind post office drops that.
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The Pinkerton Agency was able to use for other cases.
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But in terms of bringing the robbers to justice, the case was a bust, though Siringo had little time to dwell on the outcome. In November 1903, Siringo accepted a case.
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That he called the strangest of his career.
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A wealthy young man named Edward Wentz had recently disappeared in the Cumberland Mountains.
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Around the Virginia Tennessee border. Wentz was the son of a prominent.
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Wealthy landowner and the rumor was that Wentz had been kidnapped from Virginia and.
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Taken to Kentucky to be held for ransom. Everyone warned Siringo that it was a dangerous case in a dangerous land that.
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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.
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For more than a hundred years. And if they felt threatened, they might not think twice about disappearing. A nosy detective.
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Siringo arrived in eastern Kentucky and quickly realized it was not.
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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.
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In fact, everyone suspected Siringo was a.
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Pinkerton who was looking for Wentz or.
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A federal agent poking around about illegal alcohol production.
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A few days in eastern Kentucky revealed nothing. So Siringo ventured into Virginia where Wentz had been taken. About a month or so into his time in Virginia, Siringo became friendly with.
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A woman named Lottie.
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In early 1904 she revealed that Edward Wentz was already dead. According to Lottie, Wentz's kidnapping was had nothing to do with his family's wealth.
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It was because Wentz opposed saloons operating near the coal fields the Wentz family owned.
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Wentz, it seemed, didn't like the idea of his coal miners getting liquored up.
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Before, during or after work.
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A feud broke out between Wentz and.
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The saloon owners and the saloon owners killed Edward Wentz.
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A couple months later, Wentz's body was.
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Found in the woods near Kellyville, Virginia.
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And had been made to look like Wentz took his own life.
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He suffered a single gunshot to the chest from a.32 caliber pistol which was found nearby.
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Most people believe the scene was staged, but no one was charged with the.
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Murder of Edward Wentz.
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A grand jury ruled the death was.
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Accidental and declared the pistol had misfired.
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Siringo was certain the case was murdered, but in the tight knit communities of.
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The Appalachian Mountains he could take the case no further. Siringo 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.
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How long he could keep chasing outlaws. He began to wonder if it was time to turn in his Pinkerton badge. In the summer of 1907, 52 year old Charlie Siringo accepted His final assignment.
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He was tasked with being the bodyguard.
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For a confessed killer named Harry Orchard.
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Orchard was a miner in Idaho, and two years earlier he assassinated the former governor of Idaho, Frank Stunenberg.
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The assassination was linked to ongoing labor.
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Disputes between the miners and the mine.
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Owners in the Idaho panhandle, a dispute Siringo was all too familiar with.
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Siringo had infiltrated the miners unions in the Coeur d' Alene region 15 years earlier in 1892.
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The case eventually led to the conviction of several union leaders, including George Pettibone. But Pettibone's 1892 conviction had been overturned.
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When he was released, he helped create the Western Federation of Miners with an activist named Bill Haywood.
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Simmering tensions between the WFM and the.
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Mine owners boiled over and eventually Governor Steunenberg was killed.
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Harry Orchard confessed to the crime, but he said he was acting on orders from Bill Haywood.
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Now, in the summer of 1907, Orchard was ready to testify against Haywood.
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And Charlie Siringo was supposed to make sure Orchard lived to take the stand. To defend Bill Haywood and George Pettibone.
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The Western Federation of Miners employed its.
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Go to attorney, the soon to be legendary lawyer Clarence Darrow. Darrow had been making a name for.
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Himself as a labor lawyer and he.
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Would continue to do so for a few more years, during which he defended.
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The McNamara brothers for bombing the LA Times building in 1910. After that trial, the union severed ties.
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With Clarence Darrow and Darrow turned to criminal law.
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He became a household name for defending murderers Nathan Leopold and Richard Loeb and.
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Defending Tennessee teacher John Scopes in the famous Scopes monkey trial in Idaho.
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From 1906 to 1908, Clarence Darrow delivered impassioned speeches to juries and he won.
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Acquittals for Bill Haywood and George Pettibone.
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As it happened, Charlie Siringo's job as a bodyguard for the confessed killer Harry Orchard wasn't very eventful. But shortly after the trial, Siringo 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. Siringo 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 Siringo did as a Pinkerton. After Haywood's trial, Siringo returned to Denver and resigned from service. McParland tried to convince Siringo to stay as a superintendent at another office, but but Siringo declined. Now in his 50s, Siringo couldn't keep up with bandits anymore. His 20 year career as a Pinkerton agent was over.
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Siringo moved to a ranch in New.
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Mexico with his second wife, Grace.
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But he quickly realized that life as.
C
A rancher was too slow.
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For a few years, Siringo freelanced for various detective agencies, mostly gathering information related to cattle rustling.
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During that period, Siringo decided to write about his experiences as a detective similar.
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To his previous book about life as a Texas Cowboy. In 1910, Siringo wrote A Pinkerton's Cowboy.
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A True Story of 22 Years with.
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The Pinkerton's National Detective Agency. The book promised to be an exciting.
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First hand account of life working with.
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The most famous detective agency in the country. But the Pinkertons didn't want their secrets.
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Revealed to the public and they filed.
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An injunction to stop Siringo from releasing the book. Siringo grudgingly agreed to change some names.
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And in 1912 he published a Cowboy Detective. A few years later, under a cloud of failing health and financial problems, Siringo, 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 Siringo, a cowboy detective, passed away in 1928 and was buried at Inglewood Cemetery.
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The old grounds sit directly across the.
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Street from the LA Forum, the home of the LA Lakers during the Showtime years and a couple blocks away from.
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The colossal Sofi Stadium, the current home of the LA Rams and the LA Chargers.
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Charlie Siringo lies in good company with other legends like boxer Sugar Ray Robinson.
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Musicians Ray Charles, Chet Baker, Etta James.
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And Ella Fitzgerald, actress Betty Grable, and Father Junipero Serra, the priest who rode.
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With Spanish conquistadors in the 1700s and.
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Established missions throughout California. Foreign Next time on Legends of the Old West.
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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 early frontiersmen Daniel Boone and Davy Crockett. That's next time on Legends of the Old West.
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Members of our Black Barrel plus program don't have to wait week to week to receive new episodes.
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They receive the entire season to binge.
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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 blackberrymedia.com memberships are just $5 per month.
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This episode was researched, written and produced by Joe Guerra.
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Original music by Rob Valiere. I'm Chris Wimmer. Thanks for listening.
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Host: Chris Wimmer (Black Barrel Media)
Date: August 27, 2025
This episode explores the relentless pursuit of the Wild Bunch—Butch Cassidy, the Sundance Kid, and their notorious gang—by legendary Pinkerton agent Charlie Siringo. The narrative dives deep into Siringo’s undercover escapades, setbacks, and ultimate frustrations as he attempts to wrangle the most elusive outlaws of the waning Old West. Along the way, the episode traces Siringo's dogged lawman career, introduces his colorful cast of allies and adversaries, and highlights how Wild West myth intertwines with stark reality.
Context Setting (02:07 – 05:26):
"The explosion was massive, greater than anyone anticipated. It not only blew open the safe, but it shredded the door and the roof of the express car." (04:53, Host)
Formation & Infamy (06:06 – 07:08):
"Kid Curry had the reputation for being a cold-blooded killer, the deadliest man of the Wild Bunch." (07:04, Host)
A Detective Friendship; Following Leads (07:26 – 10:18):
"Sheriff Allred had a feeling that the two newcomers weren’t prospectors. They were train robbers." (08:49, Host)
Elusive Outlaws and Misdirections (12:22 – 17:00):
“Sayles had discovered Kid Curry’s true identity. At the time, the Pinkertons did not know that Curry’s real name was Harvey Logan.” (14:04, Host)
Brushes with Death and Outlaws (17:12 – 20:06):
"He didn't know that a man was watching him intently from a backroom hiding spot. That man was Harvey Logan, alias Kid Curry." (19:40, Host)
Counterintelligence Revelations (18:53 – 19:31):
“They used a complex set of cipher codes when writing messages… and they used a system of so-called blind post offices in New Mexico, Colorado, Utah and Wyoming.” (19:00, Host)
The Limits of Law (20:21 – 22:45):
"By 1903, Charlie Siringo had had enough... it was clear he wasn’t going to catch them." (20:21, Host)
From Outlaws to Feuders (22:56 – 25:22):
"Most people believe the scene was staged, but no one was charged with the murder of Edward Wentz." (25:06, Host)
Harry Orchard & Famous Trials (25:41 – 29:06):
"Warning McParland about the lynch mob would be the last thing Charlie Siringo did as a Pinkerton." (28:01, Host)
Retirement, Writing, and Legacy (29:06 – 30:58):
“Charlie Siringo, a cowboy detective, passed away in 1928 and was buried at Inglewood Cemetery.” (30:25, Host)
The episode is rich in dramatic storytelling and historic detail. The narration maintains a respectful yet brisk Old West storytelling sensibility—melding suspense, empathy, and subtle irony as it chronicles lawmen, outlaws, and the shades of gray in between. Despite Siringo’s disappointments, his tenacity and humanity shine through, making both detective and era come alive for listeners.
Summary prepared for listeners seeking a thorough yet engaging overview of “Charlie Siringo: The Wild Bunch.”