PINKERTONS Ep. 4 | “Charlie Siringo: Cowboy Detective”

Summary

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

Release Date: August 13, 2025
Host/Author: Black Barrel Media
Podcast Title: Legends of the Old West
Episode Title: PINKERTONS Ep. 4 | “Charlie Siringo: Cowboy Detective”

---

1. Introduction to Post-Civil War America

The episode opens by setting the stage in the aftermath of the Civil War, highlighting the United States' remarkable economic growth during the Reconstruction era. As the South struggled under the Reconstruction Acts, the North experienced a manufacturing boom in textiles, steel, and oil production. The expansion of railroads fostered westward migration, leading to the influx of settlers into the western territories.

Key Points:

• Economic prosperity contrasted with social tensions.
• Rise of industrial magnates like Andrew Carnegie and John D. Rockefeller, who amassed immense wealth and were dubbed "robber barons."
• Growing income disparity catalyzed labor movements and unrest.

Notable Quote:

"Throughout the 1870s and early 1880s, wealth became concentrated in the hands of a few." – Chris Wimmer [02:06]

2. The Haymarket Affair: A Catalyst for Change

The narrative delves into the escalating tensions between laborers and industrialists, culminating in the Haymarket Affair of May 4, 1886. The episode recounts the general strike demanding an eight-hour workday, the subsequent violent clash at McCormick Reaper Works, and the infamous bombing at Haymarket Square that resulted in multiple fatalities.

Key Points:

• May 1, 1886: Nationwide general strike for an eight-hour workday.
• May 3, 1886: Violent confrontation at McCormick Reaper Works in Chicago.
• May 4, 1886: Rally at Haymarket Square disrupted by a bomb, leading to chaos, deaths, and injuries.

Notable Quote:

“Several strikers were wounded and between two and six were killed.” – Narrator [04:32]

3. Charles Siringo: From Cowboy to Detective

Amidst the chaos of the Haymarket Affair, the retired cowboy and author Charles Siringo is introduced. Disturbed by the events, Siringo resolves to seek justice by joining the Pinkerton Detective Agency to uncover the truth behind the bombing.

Key Points:

• Charles Siringo's background as a Texas cowboy with a rich, adventurous history.
• Personal tragedy with the early death of his father, Antonio Siringo.
• Siringo's transition from ranch life to authoring "A Texas Cowboy," establishing his literary credentials.
• Decision to join Pinkerton Detective Agency driven by a desire to investigate the Haymarket bombing.

Notable Quote:

“He decided to change professions and become an operative for the Pinkerton Detective Agency.” – Narrator [05:36]

4. Joining the Pinkerton Detective Agency

Siringo's entry into the Pinkerton Agency is detailed, highlighting his interview with William Pinkerton and his subsequent assignments. His initial task involves monitoring jury members for potential bribery during the Haymarket trial, which ultimately proves unsuccessful as the true bomber remains unidentified.

Key Points:

• Siringo's successful application and interview process with the Pinkertons.
• Assignment to oversee jury conduct during the Haymarket trial.
• Frustration over the inability to identify the actual bomber, leading to reassignment.

Notable Quote:

“But Charlie Siringo would never get the chance to find out.” – Chris Wimmer [17:55]

5. Assignment in Pagosa Springs: Combating Corruption

Siringo is reassigned to lead the Pinkerton office in Denver, where he is tasked with addressing the turmoil in Pagosa Springs, Colorado. The county is embroiled in corruption led by the powerful Archuleta brothers, who manipulate elections and maintain an iron grip over the region.

Key Points:

• Pagosa Springs' political instability due to the Archuleta brothers' corrupt practices.
• Siringo's infiltration of the rebellion, adopting the alias "Charlie Anderson."
• Strategic maneuvers to thwart an impending rebel attack by warning the commissioners.
• Successful dismantling of the rebellion through undercover work, despite personal conflicts and ethical dilemmas.

Notable Quote:

“He accomplished his mission and restored order on behalf of the county commissioners.” – Narrator [24:17]

6. The Manhunt for Bill McCoy in Wyoming

Siringo's next major assignment involves tracking down the infamous desperado Bill McCoy in Wyoming. The episode chronicles Siringo's undercover efforts, including infiltrating McCoy's gang, devising deceptive tactics, and navigating the perilous dynamics within the outlaw group.

Key Points:

• Introduction of Bill McCoy, a notorious outlaw responsible for the killing of Deputy Sheriff Charles Gunn.
• Siringo's strategic infiltration of McCoy's gang under the guise of a cowboy outlaw named Henderson.
• Close encounters and moral conflicts arising from Siringo's undercover role, including near-escapes and partial successes.
• Ultimately, the legal intricacies prevent Siringo from capturing McCoy, highlighting the challenges faced by detectives of the era.

Notable Quote:

“Charlie Siringo was on thin ice. The two sides continued their standoff at the bridge...” – Chris Wimmer [24:06]

7. Reflections on the Detective Life and Ethical Dilemmas

The episode concludes with insights into the complexities of undercover detective work. Siringo grapples with the emotional toll of betraying individuals he had come to respect and the inherent dangers of his assignments. His experiences underscore the thin line between law enforcement and personal morals in the turbulent American West.

Key Points:

• The emotional and ethical challenges of undercover work.
• Siringo's reflections on his inability to capture Bill McCoy and the broader implications for justice.
• The cyclical nature of success and failure in the life of a detective.

Notable Quote:

“You win some, you lose some, especially in a region as expansive as the American West.” – Chris Wimmer [33:55]

8. Teaser for the Next Episode

The episode wraps up with a preview of the next installment, where James McParland takes over the Denver office, assigning Siringo to infiltrate mining unions. This new role presents fresh challenges as Siringo confronts the desires of miners striving for decent livelihoods, juxtaposing his pursuit of outlaws with the everyday struggles of ordinary workers.

Notable Quote:

“It was a very different thing to work against miners who just wanted to make a decent living.” – Chris Wimmer [34:35]

---

Conclusion

"PINKERTONS Ep. 4 | 'Charlie Siringo: Cowboy Detective'" offers an in-depth exploration of Charles Siringo's transition from a rugged Texas cowboy to a determined detective within the Pinkerton Agency. Through engaging storytelling, the episode captures the essence of post-Civil War America, the labor struggles of the era, and the personal and professional challenges faced by those seeking justice in the tumultuous Old West.

Listeners are treated to a richly detailed narrative, complete with historical context, character development, and the moral complexities inherent in Siringo's detective work. The inclusion of notable quotes with timestamps enhances the immersive experience, making the summary both informative and engaging for those new to the podcast.

---

Additional Information:

• Research, Writing, and Production: Joe Guerra
• Original Music: Rob Valiere
• Memberships: Members of Black Barrel Media's program receive entire seasons upfront, exclusive bonus episodes, and an ad-free experience. Sign up at blackberrymedia.com.

Transcript

[Sponsor Host]

Hey friends, let me put you on to something that will completely change your morning Cooper's Cask Coffee and this is not your average cup of Joe. Cooper's takes high quality grade one single origin beans. We're talking from Colombia, Rwanda, Sumatra. And they do something totally different because before they even roast the beans, they age them inside real used spirit barrels like bourbon, whiskey, rum, even wine barrels. And the result is that each batch picks up complex rich flavors like warm vanilla oak, caramel, dark fruit flavors that you typically associate with spirit. Aged in barrels but without a drop of alcohol, it's just full bodied, insanely smooth coffee with depth unlike anything you've ever tasted. Their Bourbon Barrel Aged Colombian has this bold rustic sweetness with cocoa and a mellow bourbon finish. And the Rum Barrel Aged Rwanda has hints of molasses, sweet spice and dark toffee. Cooper's Cass Coffee is kind of like if your favorite coffee and your favorite spirit had a flavor packed baby. Whether you're a serious coffee lover, a whiskey fan, or just someone who wants to shake up your morning, Cooper's deliver something really special. Be sure to go check them out at L O T o w coffee dot com. They've got sampler packs, subscriptions and gift sets too. That's l o t o-w coffee.com Trust me, you've never had coffee like this before.

[Adam Rogers]

This episode is brought to you by FX's alien Earth, the official podcast. Each week, host Adam Rogers is joined by guests, including the show's creator, cast and crew. In this exclusive companion podcast, they will explore story elements, deep dive into character motivations, and offer an episode by episode behind the scenes breakdown of each terrifying chapter in this new series. Search FX's alien Earth wherever you listen to podcasts.

[Chris Wimmer]

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.

[Narrator]

Controlled oil, and JP 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.

[Chris Wimmer]

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 1, 1886, tens of thousands of laborers across Chicago put down their tools for a general strike. Their demand was they wanted an eight hour work day. And Chicago wasn't the only city affected. New York, Detroit, Cincinnati and Milwaukee all saw men walk off the job.

[Narrator]

In Chicago. On the third day of the strike.

[Chris Wimmer]

Unarmed workers gathered in front of the McCormick Reaper Works for a rally.

[Narrator]

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.

[Chris Wimmer]

Factory opened and the strikers watched as.

[Narrator]

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.

[Chris Wimmer]

Soon gunshots rang out.

[Narrator]

Several strikers were wounded and between two and six were killed. The following evening, May 4, a rally.

[Chris Wimmer]

Was held at Haymarket Square on the.

[Narrator]

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.

[Chris Wimmer]

The rally didn't escalate into violence. As the rally drew to a close, one hundred and eighty police officers arrived.

[Narrator]

To disperse the crowd.

[Chris Wimmer]

Suddenly, a thundering boom roared across the square. A bomb had been thrown into the crowd.

[Narrator]

Confusion and chaos took hold as police.

[Chris Wimmer]

Officers opened fire on the crowd, only.

[Narrator]

To be met with bullets coming from.

[Chris Wimmer]

Some of the strikers.

[Narrator]

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.

[Chris Wimmer]

Affair or the Haymarket Riot.

[Narrator]

Just a few blocks from the square, a retired cowboy and author named Charles Siringo heard the explosion and the gunshots.

[Chris Wimmer]

When Siringo read about the events the.

[Narrator]

Next day, he was convinced he needed.

[Chris Wimmer]

To find the person who threw the bomb.

[Narrator]

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.

[Chris Wimmer]

I'm your host Chris Wimmer and this.

[Narrator]

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 four Charlie Siringo part one cowboy detective two months after the Haymarket affair, 31 year old Charlie Siringa walked into the Pinkerton Agency's Chicago office and handed over a letter of recommendation. Later that day, Siringo interviewed with William Pinkerton, the son of the agency's founder. William liked what he saw. More importantly, he liked Siringo's background. Which made sense because prior to applying to the agency, Charlie Siringo had lived a completely different life. Siringo hailed from Matagorda Bay, Texas, just off the Gulf Coast. His father, Antonio Siringo, 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 Matagorda. 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 Siringo died. Antonio's dream had been to settle down and 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.

[Chris Wimmer]

Lost sight of wanting to work with cattle.

[Narrator]

Siringo got his first chance to become.

[Chris Wimmer]

A cowboy when he was 12.

[Narrator]

Driving Texas Longhorns alongside vaqueros. He learned everything about being a cowboy.

[Chris Wimmer]

The land, the cattle, how to lasso.

[Narrator]

How to speak a little Spanish and mavericking. That is the process of branding allegedly stray cattle. It was a life young Siringo loved.

[Chris Wimmer]

But it didn't last very long.

[Narrator]

A few months after his first experience.

[Chris Wimmer]

On the trail, Siringo learned that his mother, Bridget married a man named William Carrier.

[Narrator]

The plan was to move from Texas to Michigan.

[Chris Wimmer]

So Siringo's mother sold the ranch, packed their things and boarded a steamboat to.

[Narrator]

Head for the Mississippi river, which would take the family north to Michigan.

[Chris Wimmer]

But neither the marriage nor the trip lasted long. William Carrier was a drunkard who fell.

[Narrator]

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.

[Chris Wimmer]

Supposedly, a drunken Carrier got into a.

[Narrator]

Fight with a crowd in a small town on the Illinois side of the.

[Chris Wimmer]

River and ran off. Charlie Siringo never saw William Carrier again.

[Narrator]

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 Siringo stayed in Illinois for a few more months.

[Chris Wimmer]

And and worked a series of odd jobs.

[Narrator]

After not hearing from his family for quite a while, Siringo decided to start making his way back to his home in Texas. While traveling south, Siringo met a shipping agent named William Myers, and Myers offered.

[Chris Wimmer]

To take Siringo in. Siringo moved in with Myers in New Orleans and attended the widely respected Fisk School. But while Siringo appreciated Meyer's hospitality, he couldn't stand the Fisk School and he.

[Narrator]

Often got into fights with the other boys. With each passing day, Siringo learned how.

[Chris Wimmer]

To hold his own in a strange land and earned a reputation as someone not to be messed with. But Siringo couldn't ignore the pull of Texas. Around the time he was 15, Siringo abruptly left New Orleans and sailed back to Texas. In his hometown of Matagorda, he found.

[Narrator]

Work as a cowboy for a cattle baron and named Abel Shanghai Pierce.

[Chris Wimmer]

For the next 15 years, Charlie Siringo.

[Narrator]

Worked as a cowboy. He herded tens of thousands of cattle.

[Chris Wimmer]

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, Siringo came across a group of strangers near the ranch's land. One of those strangers, as it turned out, was Billy the Kid. Siringo and Billy seemingly got along and Siringo allowed Billy and his friends to squat on the ranch for a short time. But after Billy became a wanted man, Siringo turned on him. At the end of 1880, Sheriff Pat Garrett and a posse came to the area looking for Billy. Siringo decided to help in the manhunt and he loaned some men from the ranch to Garrett.

[Narrator]

A few of the ranch hands were.

[Chris Wimmer]

Present when Garrett captured Billy in New Mexico, and at about that time, Siringo was growing tired of the cowboy life. In the early 1880s, he met and married Mamie Lloyd and called it quits as a cowboy.

[Narrator]

During retirement, he got the idea to.

[Chris Wimmer]

Write a memoir about his Cowboy days.

[Narrator]

In 1885, he published the first edition of A Texas Cowboy. At the time of its publication, there weren't many first hand accounts of life.

[Chris Wimmer]

On the range and the book became a minor hit. Realizing he might have talent as a.

[Narrator]

Writer, Siringo moved his family to Chicago.

[Chris Wimmer]

In the early spring of 1886, Siringo.

[Narrator]

Planned on expanding the book for a second edition, but no sooner had he arrived in the Windy City than violence caused him to change his career path.

[Sponsor Host]

You chose to hit play on this podcast today. Smart Choice Progressive loves to help people make smart choices. That's why they offer a tool called Auto Quote Explorer that allows you to compare your Progressive car insurance quote with rates from other companies so you save time on the research and can enjoy.

Savings when you choose the best rate for you.

Give it a try after this [e-mail] Progressive Casualty Insurance Company and affiliates not available in all states or situations.

Prices vary based on how you buy this podcast you're listening to it was once just a dream. A dream that became reality not by accident, but because someone decided not to let the what ifs keep them from creating something they believed in. Starting your own business is a dream lots of us share, but too many let it remain just a dream. Don't hold yourself back from creating what you believe in and turn those what ifs into why nots with Shopify by your side. Shopify is the commerce platform behind millions of businesses around the world and 10% of all e commerce in the US from household names like Mattel and Gymshark to brands just getting started. What if I can't design a website? Shopify's got you with beautiful ready to go templates to match your brand's style. What if I need a hand? Get help with everyday tasks like enhancing product images, writing product descriptions, or generating discount codes with Shopify's AI tools created for commerce. What if people haven't heard about my brand? Shopify helps you find your customers with easy to run email and social media campaigns. And what if I get stuck? Shopify is always around to share advice with their award winning 24. 7 customer support. So turn those dreams into and give them the best shot at success with Shopify. Sign up for your $1 per month trial and start selling today at shopify.com realm go to shopify.com realm shopify.com realm.

[Narrator]

It didn't take long for Siringo to see that Chicago was a pot ready to boil. Siringo recognized that tensions were high between.

[Chris Wimmer]

The workers and the bosses, so when.

[Narrator]

He and Mamie went to bed on the evening of May 4, 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 3, striking workers led by August Spears held a rally outside of McCormick Reaper Works, a company which manufactured harvesting equipment.

[Chris Wimmer]

The peaceful demonstration turned violent when strikebreakers arrived and laborers began throwing rocks at them.

[Narrator]

Police entered the fray, which resulted in.

[Chris Wimmer]

The death of several men and many more wounded.

[Narrator]

The next night, on May 4, a.

[Chris Wimmer]

Rally was held at Haymarket Square to.

[Narrator]

Honor the fallen from the previous day.

[Chris Wimmer]

180 police officers arrived to disperse the crowd of 2000. As the men and women left, someone.

[Narrator]

Threw a bomb into the crowd. The explosion caused police and some armed strikers to open fire.

[Chris Wimmer]

When the smoke cleared, at least 10 people were dead and dozens more were wounded. A few blocks away, Charlie Siringo awoke.

[Narrator]

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, Siringo learned new details.

[Chris Wimmer]

Of the deadly events in Haymarket Square.

[Narrator]

And he decided to become a detective.

[Chris Wimmer]

To find the man who threw the bomb. The Pinkerton Detective Agency's longtime headquarters was in Chicago.

[Narrator]

On June 29, Siringo walked into a local bank that he was acquainted with.

[Chris Wimmer]

And asked the banker for a letter of recommendation. The banker obliged and with the letter in hand, Syringo walked over to the Pinkerton office and asked to see William Pinkerton, the eldest son of the agency's founder.

[Narrator]

But as a newcomer, Siringo couldn't see.

[Chris Wimmer]

William Pinkerton right away. Siringo's letter of recommendation earned him a.

[Narrator]

Meeting with Captain Mike Farley.

[Chris Wimmer]

According to Siringo, Captain Farley put him through the test, though unfortunately, Siringo never explained the so called test. Whatever it was, Siringo passed with flying.

[Narrator]

Colors and then interviewed with William Pinkerton.

[Chris Wimmer]

Pinkerton liked Siringo, especially Siringo's background as a cowboy. Pinkerton had spent some time in the.

[Narrator]

West while chasing various train robbers during.

[Chris Wimmer]

The 1870s and he liked the idea of a homegrown cowboy as a detective. Pickerton asked Siringo for for more references and Siringo gave him a few names, including Sheriff Pat Garrett. In short order, Charlie Siringo was hired by the Pinkerton Detective Agency. Siringo desperately wanted to bring the Haymarket bomber to justice.

[Narrator]

But by the time he was hired by the agency, eight alleged conspirators were already arrested and on trial. So Siringo's first job as a detective was was to keep an eye out for potential jury bribes.

[Chris Wimmer]

Throughout the summer and early fall, Siringo.

[Narrator]

Tailed jury members with the hope of seeing money exchange hands.

[Chris Wimmer]

But he saw no evidence of jury tampering. At the end of the trial, the.

[Narrator]

Eight defendants, including August Spears, were found.

[Chris Wimmer]

Guilty of accessory to murder.

[Narrator]

Five defendants, including Spears, were sentenced to hang. Two were sentenced to life in prison and and one was given 15 years. Though to this day no one knows who actually threw the bomb in Haymarket Square. And Charlie Siringo would never get the chance to find out.

[Chris Wimmer]

Shortly after the trial, Siringo was reassigned.

[Narrator]

To the brand new office in Denver. William Pinkerton needed a cowboy detective and Siringo fit the bill. So in October 1886, Charlie and Mamie packed up and headed to Chicago.

[Chris Wimmer]

While briefly working in Chicago, Siringo learned.

[Narrator]

How to be a city detective, which.

[Chris Wimmer]

Involved a lot of shadowing people.

[Narrator]

But as a cowboy detective, he knew he'd be infiltrating gangs in rugged landscape. As he started to re acclimate to.

[Chris Wimmer]

Life in the west, he quickly discovered.

[Narrator]

The most irritating aspect of his transfer to Denver.

[Chris Wimmer]

His supervisor, Charles Eames, had turned the Denver office into nothing more than an extortion racket.

[Narrator]

Siringo 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.

[Chris Wimmer]

Six months after Siringo's transfer, he received.

[Narrator]

His first major assignment, one which would gratefully take him away from Denver and Charles Eames. There was trouble in Pagosa Springs, Colorado.

[Chris Wimmer]

Along the border of Colorado and New.

[Narrator]

Mexico, Pagosa Springs was in Archuleta County. And at the time, the county had an unusual dynamic. Most of the commissioners who ran the.

[Chris Wimmer]

County didn't live in Colorado. The majority, including the Archuleta brothers, lived.

[Narrator]

Several miles south in New Mexico.

[Chris Wimmer]

The Archuleta 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 Archuleta brothers were known to buy elections or to send their sheep herders to town on election day to stack the vote. In early 1887, Archuleta county held an election for various positions. To no one's surprise, the Archuleta 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 Archuleta county were fed up with the commissioners and they decided to rebel. The insurgents drove the commissioners out of Pagosa Springs.

[Narrator]

They burned down a commissioner's house and.

[Chris Wimmer]

Forced another to resign his post under.

[Narrator]

The threat of a bullet to his head. Before long, anarchy took hold of Archuleta.

[Chris Wimmer]

County and the commissioners hired the Pinkerton.

[Narrator]

Agency to help put down the rebellion.

[Chris Wimmer]

The Pinkertons sent Charlie Siringo. Siringo traveled down to Pagosa Springs under the name Charlie Anderson.

[Narrator]

His cover was that he was a wanted man from Texas who had killed three Mexicans. Siringo's contact was a woman named Mrs. Scase. Mrs. Scase was the wife of a.

[Chris Wimmer]

County commissioner who had been run out of town. Though Commissioner Skase was gone, his family was allowed to stay. Shortly after arriving, Siringo rode to the ranch of a rebellion member known as Gordon G. Using his fake backstory, Siringo was easily able to convince Gordon G. That he was a ruffian and a hired gun. Looking for work. Gordon G. Introduced Siringo to the rebellion's leader, E.M. taylor.

[Narrator]

Taylor was desperate for help, and he welcomed Siringo with open arms. Over the next few days, Siringo learned.

[Chris Wimmer]

That the rebels and the commissioners had gathered on opposite sides of the San Juan river, which ran through town.

[Narrator]

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.

[Chris Wimmer]

One night, Siringo discovered that the rebels were planning a surprise attack. The plan was to sneak across the.

[Narrator]

Bridge in the early morning hours and.

[Chris Wimmer]

Start a fire where the commissioners slept. While the commissioners reacted to the blaze, the rebels would open fire with weapons. Siringo knew he couldn't let that happen. Hours before the attack, Siringo 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.

[Narrator]

Culprit and they stationed men outside her.

[Chris Wimmer]

House to watch her. Siringo knew the house was being watched, but for whatever reason, he decided he needed to leave messages in the home.

[Narrator]

Later that same night, his secret routine for communication was to leave messages behind a painting in her house.

[Chris Wimmer]

That night, while the rebels were having a dance, Siringo managed to sneak around the back of the house and slip inside. After leaving his message, Siringo returned to the dance. When Siringo got back to the dance.

[Narrator]

He was surrounded by angry rebels. His absence had been noticed and allegedly someone saw Siringo near Mrs. Skase's house. Many of the rebels were now convinced.

[Chris Wimmer]

That Charlie Siringo was the traitor and they were ready to hang him.

[Narrator]

Siringo knew he wouldn't survive if he pulled his gun. So there was only one Deny, deny, deny it. In a rage, Siringo demanded to know who claimed to have seen him.

[Chris Wimmer]

A man stepped forward and Siringo yelled at him.

[Narrator]

Siringo's performance was so convincing that the accuser retracted his statements. Charlie Siringo lived to see another day, but he was on thin ice. The two sides continued their standoff at.

[Chris Wimmer]

The bridge, but after days of a.

[Narrator]

Stalemate, the Rebels decided to compromise. They proposed that they were willing to share power with the commissioners, and the.

[Chris Wimmer]

Commissioners agreed to the proposal.

[Narrator]

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 Siringo's testimony. He accomplished his mission and restored order on behalf of the county commissioners, and with that, he rode back to Denver.

[Chris Wimmer]

For the next job.

[Sponsor Host]

Mint is still $15 a month for premium wireless, and if you haven't made the switch yet, here are 15 reasons why you should 1. It's $15 a month.

2.

Seriously, it's $15 a month.

[Narrator]

3.

[Sponsor Host]

No big contracts.

4.

I use it. 5. My mom uses it. Are you playing me off? That's what's happening, right? Okay, give it a [e-mail] Switch upfront.

Payment of $45 per three month Plan 15 $15 per month equivalent required New customer offer first three months only, then full price plan options available. Taxes and fees extra.

See mint mobile.com this message is sponsored.

By Greenlight with school out, summer is the perfect time to teach our kids real world money skills they'll use forever. Greenlight is a debit card in the number one family finance and safety app used by millions of families, helping kids learn how to save, invest and spend wisely. Parents can send their kids money and track their spending and saving while kids build money, confidence and skills in fun ways. Start your risk free Greenlight trial [e-mail] Spotify that's greenlight.com Spotify.

[Narrator]

Newspapers claimed a.

[Chris Wimmer]

Man named Bill McCoy was a Texas.

[Narrator]

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.

[Chris Wimmer]

The stomach and once in the head.

[Narrator]

McCoy went into hiding for about a.

[Chris Wimmer]

Month, and then, for reasons that have only been described as foolishness, he decided.

[Narrator]

To return to Lusk.

[Chris Wimmer]

While eating at a restaurant, a small.

[Narrator]

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.

[Chris Wimmer]

Two months later, at the start of.

[Narrator]

October, McCoy cut a hole in the roof of his cell and and slipped out into the Wyoming night. He was a fugitive on the run, and Charlie Siringo was sent to Wyoming to find him. Siringo arrived in Cheyenne and sat down.

[Chris Wimmer]

With District Attorney Colter Skoll. Skoll explained the events leading up to.

[Narrator]

McCoy's escape, but also gave Siringo the.

[Chris Wimmer]

Name of an accomplice. Skull told Siringo that that the night.

[Narrator]

McCoy escaped, a man named Tom hall.

[Chris Wimmer]

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 Siringo that the place was.

[Narrator]

Heavily guarded by wanted Texas desperados. In fact, another detective agency had recently.

[Chris Wimmer]

Sent three men to the ranch, and.

[Narrator]

They had been lucky to escape with their lives.

[Chris Wimmer]

After gathering the information, Siringo saddled up and started toward the ranch. Along the way, he paused at the Roundup Number 5 Saloon. With a drink in hand, Siringo became.

[Narrator]

Acquainted with the saloon's owners, an older couple with the last name Howard.

[Chris Wimmer]

Over the next few hours, Siringo drank with the Howards.

[Narrator]

He claimed he was from Texas and.

[Chris Wimmer]

He was on the run. So Siringo told Mr. Howard that he.

[Narrator]

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.

[Chris Wimmer]

Mr. Howard knew that Siringo was referring to Tom Hall's ranch and warned him to stay away. The man holed up there would kill a stranger on sight, Texan or no Texan. But Siringo wasn't scared. If anything, he was satisfied to know.

[Narrator]

That Tom hall and maybe Bill McCoy was still at the ranch. So he bought a bottle of whiskey from Mr. Howard and rode toward the ranch.

[Chris Wimmer]

As Siringo trotted along, he devised a.

[Narrator]

Plan to ingratiate himself with the desperados.

[Chris Wimmer]

He'd fake a broken leg near the ranch.

[Narrator]

Siringo hopped off his horse, tore his jeans and scratched his leg and knee.

[Chris Wimmer]

To make them look injured. Luckily, an old bullet wound would help sell the deception. Then Siringo got back on his horse.

[Narrator]

And tied his boot in a way that made it look like it was dangling.

[Chris Wimmer]

Not long after creating the ruse, Siringo.

[Narrator]

Spotted a few cabins in the distance. As he approached, a dozen armed men.

[Chris Wimmer]

Filed out of the cabins.

[Narrator]

They surrounded the newcomer on horseback. And then a tall, lanky man stepped.

[Chris Wimmer]

Forward and said, what in the hell are you doing here?

[Narrator]

The tall, lanky man was Tom hall, and now Charlie Siringo had to pray he was a good liar. Siringo said his name was Henderson and.

[Chris Wimmer]

That he had a broken leg.

[Narrator]

Instantly, Hall's gruff, intimidating attitude changed.

[Chris Wimmer]

He and his men helped Siringo off the horse and carried him into a cabin. Hall inspected Siringo's knee and informed him that it was only sprained.

[Narrator]

While huddled around a fire, Siringo recognized a man from his childhood in Texas, a guy named Jim McChesney. Siringo feared that McChesney would also recognize.

[Chris Wimmer]

Him, and Siringo tried to get ahead of it.

[Narrator]

He asked McChesney about a girl they both knew, which confused McChesney. It was clear that McChesney didn't did not recognize Charlie Siringo. McChesney, like the others, believed Siringo, was a cowboy outlaw who called himself Henderson.

[Chris Wimmer]

As Siringo and McChesney talked, Siringo insinuated that he was a man from their past who had killed a family back in 1872. McChesney bought the lie that Siringo was a killer from Texas whose name was Henderson. That evening, Siringo was given Hall's room to rest. Unbeknownst to him, hall and the rest of the men quietly debated what to do with Siringo. Three of the men feared Siringo was a detective and wanted to hang him. But McChesney vouched for Siringo, and Siringo was spared the noose. Siringo 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.

[Narrator]

Foreign.

[Chris Wimmer]

The weeks following their initial meeting, Siringo continued to play up his bum leg, and he slowly won the confidence of the gang. Eventually, talk around the campfire turned to Siringo's target, Bill McCoy. Unfortunately for Siringo, Bill McCoy was nowhere near Wyoming. In fact, he likely wasn't even in the United States.

[Narrator]

Tom hall said that after McCoy escaped.

[Chris Wimmer]

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. Siringo 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, Siringo knew There was a chance that McCoy might still be in the country.

[Narrator]

Siringo needed to get a message to.

[Chris Wimmer]

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, Siringo saw an opportunity to slip away. He found a hotel and wrote a.

[Narrator]

Message to the Denver office, with which.

[Chris Wimmer]

Advised the agency to send a posse to New Orleans.

[Narrator]

Maybe they could catch McCoy before he.

[Chris Wimmer]

Sailed out of the country.

[Narrator]

Siringo remained with hall and the gang.

[Chris Wimmer]

For at least a few more weeks, drinking and getting to know their various misdeeds.

[Narrator]

But as time passed, Siringo realized he.

[Chris Wimmer]

Was never going to catch McCoy in Wyoming.

[Narrator]

And the fact that he hadn't received.

[Chris Wimmer]

Secret correspondence out of New Orleans solidified.

[Narrator]

The idea that McCoy successfully fled to South America.

[Chris Wimmer]

But all was not lost. Siringo had gained enough information on Tom.

[Narrator]

Hall, Jim McChesney and the others to make a solid case against them. One night, while the others were asleep.

[Chris Wimmer]

Siringo sneaked away and sent a message to law enforcement in Cheyenne.

[Narrator]

The next morning, a posse arrived and.

[Chris Wimmer]

Arrested Tom hall and the gang.

[Narrator]

Realizing that Siringo wasn't around, hall allegedly.

[Chris Wimmer]

Said, that damned Henderson is at the bottom of this.

[Narrator]

Siringo did eventually testify to a grand jury about the men he helped arrest, but he didn't like it. Siringo became fond of hall and McChesney, and he felt guilty about turning them in. He soon realized that attachment was a.

[Chris Wimmer]

Real danger of undercover work. If there was any consolation for Siringo, unknown legal technicalities caused the case to collapse, and Tom Hall, Jim McChesney and the others walked free. Charlie Siringo 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.

[Narrator]

Next time on Legends of the Old.

[Chris Wimmer]

West, famed Pinkerton Detective James McParlin takes over the Denver office and starts sending Charlie Siringo 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 blackberrymedia.com memberships are just $5 per month. This episode was researched, written and produced by Joe Guerra. Original music by Rob Valiere. I'm Chris Wimmer. Thanks for listening.

[Sponsor Host]

What do you think makes the perfect snack?

Hmm, it's gotta be when I'm really craving it and it's convenient.

Could you be more specific?

When it's cravinient. Okay, like a freshly baked cookie made with real butter, available right down the street at am, pm Or a savory breakfast sandwich I can grab in just a second at a.m. pM.

I'm seeing a pattern here.

Well, yeah, we're talking about what I.

Crave, which is anything from ampm.

What more could you want? Stop by AMPM where the snacks and drinks are perfectly craveable and convenient. That's Cravenians ampm. Too much Good stuff.

DC politicians want to enact harmful credit card mandates that could take away your cash back and rewards points perks that stretch your budget and make life a little easier. Losing these benefits means less money for your family. Family's everyday essentials like gas and groceries. The perks you rely on could disappear, leaving you with higher costs and fewer options. Tell Congress to guard your card and oppose the Durbin Marshall credit card mandates.

[Chris Wimmer]

Paid for by Electronic Payments Coalition.