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🎙️ Mugshot Mysteries: Episode 3

The Outlaw Who Sued the Railroad – Al Jennings

Train robber. Failed candidate. Hollywood actor.
Al Jennings lived more lives than one man should… and made sure you heard about every one of them.

In this episode, we dig into the strange saga of a former attorney who picked up a gun after losing a brother, formed a ragtag gang with little success, and somehow wound up reinventing himself as a Western folk hero. From bungled heists to prison time with O. Henry, Jennings blurred the line between outlaw and opportunist...and spent decades mythologizing the difference.

📷 Instagram: @MugshotMysteriesPodcast

Show Notes & Sources:

News & Historical Records

— The Western Star (1895): Ed Jennings killed
— Kansas City Times (1897): Al Jennings captured
— Oklahoma State Capital (1899): Life sentence
— Coffeyville Daily Journal (1902): O. Henry prison era
— Minneapolis Journal (1919): Check fraud denial
— El Reno Democrat (1893): Family legal background

Archives & Articles

— Legends of America: https://www.legendsofamerica.com/al-jennings/
— True West Magazine: https://truewestmagazine.com/article/al-jennings/
— Library of America: https://storyoftheweek.loa.org/2024/09/holding-up-train.html
— Edmond Life & Leisure: https://edmondlifeandleisure.com/the-great-edmond-train-robbery-p10565-87.htm
— MIHP / History Mugs: https://www.mihp.org/2013/09/jennings-al-1863-1961/

Film & Memoir

— Silent Westerns Wiki: https://silentwesterns.fandom.com/wiki/Al_Jennings
— Thanhouser Film Co.: https://www.thanhouser.org/tcocd/Filmography_files/ind6a6duy.htm
— Beating Back (1913), Through the Shadows with O. Henry (1921) – Public domain
— Jeff Arnold’s West: https://jeffarnoldswest.com/2019/05/al-jennings-of-oklahoma-columbia-1951/

Psychological & Cultural Themes

• Outlaw Archetypes – Gunfighter Nation, Richard Slotkin
→ https://www.hup.harvard.edu/books/9780806130316
• Self-Mythologizing – Troubling Confessions, Peter Brooks
→ https://press.uchicago.edu/ucp/books/book/chicago/T/bo3649362.html
• Reinvention After Trauma – Dan McAdams, “Psychology of Life Stories”
→ https://doi.org/10.1037/1089-2680.5.2.100
• Western Mythmaking – Robert Warshow, “The Westerner” essay
• Memoir Legacy Inflation – Barbara Hochman, Biography (2001)
→ https://muse.jhu.edu/article/45391

👤 Al Jennings Mugshot

• View his mugshot here → https://itoldya420.getarchive.net/media/prisoner-at-leavenworth-federal-penitentiary-al-jennings-nara-292114-12ac8c

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Enjoyed the episode? Don’t forget to follow, rate, and leave a review. Thanks for listening. We’ll see you next time with another face… and another mystery.