Legs Diamond: A History of Kingston, NY’s Most Notorious Gangster

Eighty years ago, a raid on a Kingston bootlegging operation helped bring down notorious gangster Legs Diamond

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legs diamond

“A future in the Catskills”

Jack Diamond was born July 10, 1897, in Philadelphia to Irish immigrant parents. His mother died in 1913, and the family moved to Brooklyn. Quickly becoming a member of a street gang, Diamond’s criminal record began while still a teenager, when he robbed a jewelry store. After being jailed for desertion during World War I, Diamond went to work for big-time gangster Arnold Rothstein, the man who fixed the 1919 World Series. He also freelanced as a hit man for Jacob “Little Augie” Orgen, committing his first murder, and soon after got shot himself when Orgen was killed.

Legs began his own bootlegging business, mostly by hijacking trucks loaded with booze to fuel his speakeasies. He was outgoing and flamboyant, a womanizer (though he was married) and a terrific dancer. In fact, that’s the more likely source of his nickname, according to the late Gary Levine (no relation to me), a former professor at Columbia-Greene Community College in Hudson who published Jack “Legs” Diamond: Anatomy of a Gangster in 1995. He quickly became the target of other gangsters. By the end of the 1920s, New York had become too hot for him. He’d been shot two more times, and he needed a new base of operations.

In Legs, a fictional account of the gangster’s life, author William Kennedy envisions Diamond explaining to his attorney, Marcus, that he’s “got a future in the Catskills.”

“Don’t you think you ought to get straight first?”

“You don’t understand, Marcus. You can carve a whole goddamn empire up there if you do it right. Capone did it in Cicero. Sure there’s lots of roads to cover, but that’s all right. I don’t mind the work. But if I slow now, somebody else covers those roads. And it’s not like I got all the time in the world. The guineas’ll be after me now.”

“You think they won’t ride up to the Catskills?”

“Sure, but up there I’ll be ready. That’s my ballpark.”


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