American History Tellers

Daring Prison Escapes | Escape from Leavenworth | Episode 3

Host: Lindsey Graham
Release Date: September 17, 2025
Duration: ~39 minutes (excluding ads)

Episode Overview

This episode plunges into one of the boldest prison breaks in American history: the 1910 escape from Leavenworth Federal Penitentiary, Kansas. The story centers around Frank Grigware, a young man who steadfastly maintained his innocence in a notorious train robbery but became an unlikely legend after hijacking a supply train to ram through the prison gates. The episode brings to life the desperation, ingenuity, and resolve of the inmates, details the escalating manhunt, and follows Grigware’s decades-long evasion of capture, ultimately exploring themes of justice, redemption, and institutional failure.

Key Discussion Points & Insights

1. Setting the Stage: Life in Leavenworth (03:02 – 10:00)

• Leavenworth, built as the nation's premier federal penitentiary, was famous for its harsh conditions and strict discipline under Warden Robert McLaury.

• The narrative introduces Frank Grigware:

  • A carpenter’s son with a strong work ethic but little formal education
  • Framed as trustworthy and loyal, but naive and drawn into dubious company
  • Convicted on shaky evidence after the notorious Mud Cut train robbery (05:45)
    • “He swore he was innocent and his trial had been marked by shaky evidence and tainted testimony.” (04:07)
    • Notable trial scenes re-enacted with dialogue highlighting the questionable nature of the conviction (07:00–10:00)

• Prison life:

  • Brutal routines, enforced silence, relentless work
  • Severe punishments for infractions, including time in “the hole” (11:20)
    • “Leavenworth is hell, and I guess I’m the chief devil.” – Robert McLaury (13:38)

2. The Escape Plot: Planning the Breakout (17:10 – 23:30)

• Security Weakness:

  • Every Thursday, a supply train entered Leavenworth, providing a rare opportunity for escape.
  • Warden McLaury resisted installing a costly remote derail switch, leaving a critical vulnerability.

• Key Conspirators:

  • Arthur Hewitt: veteran escape artist and mastermind, previously led a mass breakout in 1901
  • Theodore Murdoch: skilled craftsman, carved realistic-looking wooden pistols in the carpentry shop
  • Frank Grigware: becomes crucial to the plan, desperate after his failed appeals

• Recruitment & Risks:

  • Dramatic dialogue re-enacts Grigware persuading Murdoch to trust him:
    • “Do you have any idea what happens once that siren goes off? Those guards will open fire without even blinking. I tell you, I’d rather die trying to get out than rot away in this place.” – Frank Grigware (20:56)

3. The Great Escape: The 1910 Train Hijacking (23:30 – 26:32)

• April 21, 1910: The meticulously-timed breakout unfolds:
  • Six inmates (Hewitt, Kading, Clark, Murdoch, Gideon, Grigware) move into action as the train arrives.
  • Wooden pistols and a hatchet used to overpower guards.
  • The engineer, Curtin, is forced at gunpoint to ram the steel gates.
    • “Keep your hand off that throttle … now pull the throttle open or I’ll put a bullet between your eyes." – Escaping prisoner to Curtin (01:21)
  • The train smashes through, but an incomplete railroad bridge halts their progress outside the prison.
  • The fugitives scatter into the countryside: some south, but Grigware flees alone to the north, employing clever hiding tactics.

4. The Manhunt & Its Aftermath (28:38 – 36:25)

• Immediate Pursuit:

  • Within 30 minutes, Warden McLaury organizes a 50-man posse.
  • Four escapees are recaptured within hours; only Grigware and Murdoch evade capture.

• Murdoch’s Ordeal:

  • Survives two days in freezing, stormy weather before surrendering, admitting “the prison looked like heaven” upon his return (31:10).

• Grigware’s Flight:

  • Survives in hiding for days, aided by food seized from the train engineer.
  • Receives help from a local woman, then hops a train to Minneapolis, evading law enforcement and reinventing himself as "Jim Fahey."

5. Years on the Run: The Legend of Frank Grigware (36:25 – 38:55)

• Long Manhunt:

  • The Bureau of Investigation (precursor to the FBI) pursues leads for years; his mother is constantly surveilled.
  • “If he is still alive and in the United States, most likely he would be very careful to lead a quiet, law-abiding life in order to avoid any possibility of being arrested and later identified.” – Federal agent (38:25)

• Life in Canada:

  • Grigware, as Jim Fahey, becomes an upstanding citizen, naturalizes as a Canadian, serves as a mayor, and raises a family.
  • His past is only revealed decades later after a fingerprint match in Canada leads to renewed public interest.
  • Extradition is refused after widespread support for Grigware in Canada:
    • “Some argued that he deserved mercy for turning his life around. Others said that he had never been guilty in the first place.” (38:48)

• Emotional Reunion:

  • After nearly three decades, his mother reunites with her son in Canada, still wearing the locket he gave her on her journey west (39:15).
  • Grigware lives out the rest of his life peacefully, dying at 91.

Memorable Quotes & Moments

• "Leavenworth is hell, and I guess I’m the chief devil." — Robert McLaury, Warden (13:38)
• "I tell you, I’d rather die trying to get out than rot away in this place." — Frank Grigware (20:56)
• “I did not know where I was going. I didn’t care… I had no plan, just a desire to stay at liberty.” — Frank Grigware, reflecting on his escape (35:22)
• "If he is still alive and in the United States, most likely he would be very careful to lead a quiet, law-abiding life in order to avoid any possibility of being arrested..." — Federal agent (38:25)
• “Her hair had turned white, but she was still wearing the small locket with Frank's picture inside that he had given her 28 years earlier.” — On Grigware’s reunion with his mother (39:15)

Notable Segments with Timestamps

• Introductory dramatization of the escape: 00:00 – 03:00
• The flawed trial and conviction of Frank Grigware: 05:45 – 10:00
• Description of life in Leavenworth and McLaury’s approach: 10:00 – 14:30
• Conspirators plan and prepare the wooden pistols: 17:10 – 21:45
• Escape sequence, train ramming the gates: 23:30 – 26:32
• Manhunt and aftermath: 28:38 – 36:25
• Grigware’s new life, capture, and ultimate freedom: 36:25 – 39:15

Episode Themes

• The episode underscores historical flaws in the justice system, resilience amid despair, the enduring hope for justice and redemption, and the ripple effects of institutional failure on individuals and families.
• It also highlights the symbolic nature of prison escapes in American lore—where both criminality and the hope for second chances intertwine.

For Listeners Who Haven’t Heard the Episode

This episode expertly weaves together the gritty reality of early 20th-century incarceration, the suspense and resourcefulness behind a notorious escape, and a poignant examination of life on the lam. Through vivid dramatizations, authentic dialogue, and factual narration, listeners gain insight into the powerlessness of the wrongfully convicted, the complex motivations for desperate action, and the surprising capacity for personal reinvention in the face of relentless pursuit.

Next Episode Preview: (39:15)
The next episode will explore a WWII-era German POW escape in the American Southwest, continuing the "Daring Prison Escapes" series.

Recommended Reading:
“Leavenworth: A Fugitive Search for Justice and the Vanishing West” by Joe Jackson

Host: Lindsey Graham
Written by: Ellie Stanton
Produced by: Airship & Wondery