Legends of the Old West - Episode 6: Doolin Daltons: Dead Outlaws

Podcast Information

• Title: Legends of the Old West
• Host/Author: Black Barrel Media
• Description: Wyatt Earp, Jesse James, and Butch and Sundance. Lakota, Comanche, and Apache. Wars, gunfights, and robberies. This show covers the toughest lawmen, the wildest outlaws, and the deadliest towns—all the people and events that shaped the American West.
• Episode: OUTLAWS Ep. 6 | “Doolin Daltons: Dead Outlaws”
• Release Date: April 23, 2025

Introduction to the Doolin Dalton Gang In this gripping episode, host Chris Wimmer takes listeners deep into the tumultuous era of the late 19th century American West, focusing on the rise and fall of the notorious Doolin Dalton Gang, also known as the Wild Bunch. The episode explores how this gang became one of the last prominent outlaw groups in a rapidly modernizing frontier, highlighting their audacious crimes, deadly confrontations, and eventual demise.

The Changing Landscape of the American West By the 1890s, the American West was undergoing significant transformation. The expansion of railroads and the advent of telephones began to erode the wildness that had once characterized the frontier. Chris Wimmer sets the stage by explaining:

“By the 1890s, it looked as if the west in general was becoming a little less wild. Railroads crisscrossed the west, and telephones were starting to replace the telegraph in a few places.” (00:56)

Despite the federal census declaring the frontier closed in 1890, lawlessness persisted, particularly in regions like Kansas and Oklahoma.

Rise of the Doolin Dalton Gang The episode chronicles the emergence of the Dalton Gang, initially led by the Dalton brothers. However, their downfall came swiftly during the Coffeyville raid in October 1892, where four members were killed, and a fifth was captured. Bill Doolin, a resilient figure among the outlaws, reorganized the remnants into the Doolin Dalton Gang.

Notable early crimes include:

• Bank Robbery in Spearville, Kansas: The gang, now rebranded, orchestrated a daring bank heist, showcasing their boldness and tactical skills.
• Train Hijacking near Cimarron, Kansas: Just seven months post-Spearville, they executed another high-stakes robbery, further cementing their reputation.

Major Confrontations and Lawmen Pursuit One of the pivotal moments discussed is the September 1, 1894 showdown in Ingalls, Oklahoma. A posse led by Deputy U.S. Marshals engaged the gang in a fierce gunfight, resulting in multiple casualties, including three deputy marshals. However, the majority of the gang escaped, highlighting both their cunning and the relentless pursuit by law enforcement.

Notable Quotes:

• Judge Frank Dale: Reflecting the increasing frustration with outlaws, he stated:

  “Marshal, this is serious. I have reached the conclusion that the only good outlaw is a dead one.” (08:50)

Spree Continues and Internal Strife Despite mounting pressure, the gang continued their spree into 1894, executing robberies in Clarkson and Pawnee, Oklahoma. However, internal challenges began to surface:

• Southwest City Robbery (May 10, 1894): A meticulously planned bank robbery in Missouri ended with significant cash loot but also intensified the hunt by authorities.
• Longview, Texas Robbery (May 23, 1894): This operation concluded disastrously with the death of Jim Wallace and two civilians, signaling a turning tide against the gang.

Decline and Demise of Key Members The relentless pursuit by lawmen, particularly the trio known as the Three Guardsmen—Heck Thomas, Chris Madsen, and Bill Tillman—led to the demise of several gang members:

• Bill Dalton: Killed on June 8, 1894, by a nine-member posse in Ardmore, Oklahoma.
• George Newcomb and Charlie Pierce: Ambushed and killed by the Dunn brothers on May 2, 1895.
• William Raidler: Captured after a shootout on September 6, 1895, and imprisoned until his parole in 1903.

Capture of Bill Doolin The leader of the gang, Bill Doolin, evaded capture for nearly two years, hiding across various territories:

• Eureka Springs, Arkansas (January 1896): Doolin attempted to find refuge in the town's bathhouses but was apprehended by Deputy U.S. Marshal Bill Tillman.
• Escape from Guthrie Jail (July 5, 1896): Doolin, along with associate Dan Clifton, orchestrated a daring jailbreak, temporarily evading recapture.
• Final Confrontation (August 25, 1896): Heck Thomas and his posse cornered Doolin in Lawson, Oklahoma. In the ensuing gunfight, Doolin was fatally wounded, marking the effective end of the Doolin Dalton Gang.

Legacy and Cultural Impact Despite their short-lived operations, the Doolin Dalton Gang left an indelible mark on American folklore:

• Cinema: The 1949 film "Doolins of Oklahoma" starring Randolph Scott immortalized their exploits.
• Music: The Eagles' 1973 album "Desperado" features tracks inspired by gang members, showcasing their lasting influence on popular culture.

“From the gang's first robbery... to the final shootout... they packed a lot of adventure and destruction into a relatively short space of time.” (09:22)

Conclusion In this episode, Chris Wimmer masterfully weaves the narrative of the Doolin Dalton Gang, illustrating the complexities of outlaw life in a changing West. Their story encapsulates the clash between law enforcement advancements and the fading era of the Wild West, highlighting themes of loyalty, ambition, and the inexorable march of progress.

Production Credits

• Research and Writing: Michael Meglish
• Producer: Joe Guerra
• Original Music: Rob Valier

Notable Quotes with Timestamps

• Chris Wimmer:

  • “By the 1890s, it looked as if the west in general was becoming a little less wild.” (00:56)
  • “From the gang's first robbery... to the final shootout... they packed a lot of adventure and destruction into a relatively short space of time.” (09:22)

• Judge Frank Dale:

  • “Marshal, this is serious. I have reached the conclusion that the only good outlaw is a dead one.” (08:50)

• Host Closing Remarks:

  • “Next time on Legends of the Old West... exciting individual stories that represent different aspects of the grandest construction project in the American west.” (09:22)

Final Thoughts For enthusiasts of Western history and outlaw legends, Episode 6 of Legends of the Old West offers a comprehensive and engaging exploration of the Doolin Dalton Gang. Through meticulous research and compelling storytelling, Chris Wimmer brings to life the perilous adventures and ultimate downfall of one of the West's most formidable outlaw groups.