July 25, 2023 ▸ History, People, True Crime

Episode 725: John Ashley: Gangster, Bootlegger, Pirate!

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On this episode of the world famous Sofa King Podcast, we talk about John Ashley. He was the head of the Ashley Gang and was said to rob 40 banks while becoming the head of Florida rum-running during prohibition. He got one of his eyes shot out by a member of his own gang, became the first pirate to attack American ships since it was a British colony, and had a feud with a one-legged sheriff who vowed to take Ashley’s eye! His lover and wife, Laura Upthegrave, was just as devious as he was. Bonnie and Clyde got all the attention, but they couldn’t hold a candle to these two!

Visit Our Sources:

Expedition Unknown

https://en.wikipedia.org/wiki/John_Ashley_(bandit)

https://indianrivermagazine.com/the-ashley-gang-what-really-happened/

https://www.crimemuseum.org/crime-library/robberies/john-ashley/

https://en.wikipedia.org/wiki/Laura_Upthegrove

https://indianrivermagazine.com/defiant-to-the-end/

https://www.flsheriffs.org/blog/entry/sheriff-bob-baker