American History Tellers Daring Prison Escapes | Escape from Leavenworth | 3
Sep 17, 2025
In 1909, Frank Grigware, a convicted train robber, faced bleak conditions at Leavenworth Penitentiary. He and five inmates executed a dramatic escape by hijacking a supply train. This daring breakout sparked one of the longest manhunts in American history. The podcast also dives into Grigware's wrongful conviction and the unjust circumstances leading to his life sentence. The harrowing realities of prison life and the desperate hopes for freedom among inmates add depth to this thrilling tale of resilience and risk.
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Daring Train Hijack Breakout
- Four prisoners seized a supply train inside Leavenworth and forced the engineer at gunpoint to ram the outer gate.
- The engine tore through the steel gate, leaving the fugitives hurtling into open country until they abandoned the train two and a half miles out.
Grigware's Arrest And Life Sentence
- Frank Grigware arrived in the West seeking fortune but got caught up with men linked to a major mail train robbery.
- He insisted on his innocence, refused a plea, was convicted with weak evidence, and sentenced to life at Leavenworth.
Design Created Security Vulnerabilities
- Leavenworth was built as a model federal prison but its construction process created security gaps like internal train access.
- Those operational weaknesses and rigid discipline under Warden McLaurie shaped both brutal conditions and escape incentives.
