Legends of the Old West

PINKERTONS Ep. 6 | “Charlie Siringo: The Wild Bunch”

Host: Chris Wimmer (Black Barrel Media)
Date: August 27, 2025

Episode Overview

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.

Key Discussion Points & Insights

Assignment: Hunt for the Wild Bunch

• Context Setting (02:07 – 05:26):

  • Siringo is tasked by Pinkerton supervisor James McParland with tracking down the masterminds of the June 1899 Wilcox, Wyoming train robbery. This heist, led by Butch Cassidy and the Sundance Kid, grabs national headlines for its audacity.
  • The train robbers used dynamite to blow open safes, making off with roughly $50,000 (nearly $2 million today).
  • This event ignities a multi-state manhunt and frames Siringo’s longest—and most elusive—case.

  "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)

The Wild Bunch: Outlaws’ Profiles

• Formation & Infamy (06:06 – 07:08):

  • Butch Cassidy, born Robert Parker, forms a loose gang of desperados, recruiting Harry Longbaugh (Sundance Kid) and Harvey Logan (Kid Curry).
  • Kid Curry’s reputation as “the deadliest man of the Wild Bunch” stands out.

  "Kid Curry had the reputation for being a cold-blooded killer, the deadliest man of the Wild Bunch." (07:04, Host)

The Relentless Pursuit Begins

• A Detective Friendship; Following Leads (07:26 – 10:18):

  • Siringo teams up with Billy Sayles; together, they craft covers as prospectors or cowboys as they chase leads through Utah, Colorado, and New Mexico.
  • Encounters with suspicious lawmen (notably Sheriff Allred of Price, Utah) add layers of danger and uncertainty.

  "Sheriff Allred had a feeling that the two newcomers weren’t prospectors. They were train robbers." (08:49, Host)

Obstacles & Frustrations

• Elusive Outlaws and Misdirections (12:22 – 17:00):

  • The investigation literally becomes a wild goose chase: Siringo follows false leads to Arkansas, narrowly misses catching members of the gang, and repeatedly finds only rumors and spent bank notes.
  • Sayles cracks a major piece by discovering Kid Curry’s true identity—Harvey Logan—and his Montana base.

  “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)

Danger & Near Misses

• Brushes with Death and Outlaws (17:12 – 20:06):

  • Siringo infiltrates Logan’s Montana horse ranch but makes little progress.
  • Siringo unknowingly comes within steps of Kid Curry in a Wyoming saloon; it is a close encounter he wouldn’t learn about until years later.

  "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)

Outlaw Communication: Codes & Blind Drops

• Counterintelligence Revelations (18:53 – 19:31):

  • The Wild Bunch used cipher codes and “blind post offices”—modern-day dead drops—to avoid capture, a tactic Siringo uncovers too late to leverage effectively.

  “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 Case Closes—With No Satisfying End

• The Limits of Law (20:21 – 22:45):

  • Siringo spends four years and travels over 25,000 miles but never apprehends his targets.
  • By the time he gives up, Cassidy and Sundance have fled to South America; Kid Curry meets a violent but ambiguous end in 1904.

  "By 1903, Charlie Siringo had had enough... it was clear he wasn’t going to catch them." (20:21, Host)

A New Kind of Case: The Death of Edward Wentz

• From Outlaws to Feuders (22:56 – 25:22):

  • Siringo investigates the disappearance (and murder) of the young, wealthy Edward Wentz—a case linked to coalfield feuds and violent local opposition to outside interference.
  • Despite Siringo’s best efforts, the community stonewalls, and Wentz’s death is officially ruled a misfire.

  "Most people believe the scene was staged, but no one was charged with the murder of Edward Wentz." (25:06, Host)

Siringo’s Final Chapter as a Pinkerton

• Harry Orchard & Famous Trials (25:41 – 29:06):

  • Tasked as the bodyguard for Harry Orchard (confessed assassin of Idaho’s former governor), Siringo finds himself close to major legal and labor history.
  • Legendary attorney Clarence Darrow defends labor leaders Haywood and Pettibone against murder charges—winning acquittals and saving them from lynch mobs.
  • Siringo’s alert about a potential lynch mob, and his role protecting witnesses, mark the conclusion of his 20-year Pinkerton career.

  "Warning McParland about the lynch mob would be the last thing Charlie Siringo did as a Pinkerton." (28:01, Host)

Siringo’s Life After the Badge

• Retirement, Writing, and Legacy (29:06 – 30:58):

  • Life as a rancher proves dull; Siringo writes the memoir A Pinkerton’s Cowboy, only to have Pinkerton lawyers force edits.
  • In failing health and financial trouble, Siringo drifts to Los Angeles, dying in 1928, his grave among Showbiz and sports legends.

  “Charlie Siringo, a cowboy detective, passed away in 1928 and was buried at Inglewood Cemetery.” (30:25, Host)

Notable Quotes & Memorable Moments

• “Siringo’s closest call occurred sometime in late 1900. One evening, Siringo sat in a saloon in Rawlins, Wyoming…That man was Harvey Logan, alias Kid Curry.” — Host, (19:31)
• “By 1903, Charlie Siringo had had enough. In his own estimation, he traveled more than 25,000 miles by horse, rail, stage and foot for four years.” — Host, (20:21)
• “He decided that life as a rancher was too slow… Siringo decided to write about his experiences as a detective.” — Host, (29:11)
• “But the Pinkertons didn’t want their secrets revealed to the public and they filed an injunction to stop Siringo from releasing the book.” — Host, (29:50)
• “Charlie Siringo, a cowboy detective, passed away in 1928 and was buried at Inglewood Cemetery.” — Host, (30:25)

Important Segment Timestamps

• [02:07] Siringo receives the Wild Bunch assignment
• [04:53] Dramatic Wilcox train robbery recounted
• [07:04] Kid Curry profiled as the 'deadliest man'
• [14:04] Sayles discovers Kid Curry's real identity
• [19:31] Siringo’s near miss with Harvey Logan in Rawlins
• [20:21] Siringo’s summary of four fruitless years, closing the case
• [22:56] Begins investigation into the Edward Wentz murder
• [25:41] Final major assignment: guarding Harry Orchard
• [28:01] Siringo’s last act as a Pinkerton—saving Darrow and Haywood from a lynch mob
• [29:35] Siringo’s memoir and Pinkerton legal battles
• [30:25] The passing and legacy of Charlie Siringo

Episode Tone and Style

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.”