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, it was said, never met a friend he didn’t double-cross. Even by the dubious standards of Depression-era gangsters, he was no good. His enemies loaded so much lead into him that rival gangster Dutch Schultz once asked his own henchmen, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”

Yet, by 1930, he was also the Hudson Valley’s biggest celebrity, a symbol of the little guy standing up to the heavy government hand of Prohibition. After being forced out of New York City, he set up operations in Catskill. Most of the locals knew he was running booze out of a brewery in Kingston. But government agents charged with enforcing the 18th Amendment could never figure out how.

Raids in the early summer of 1931 finally uncovered the subterranean secret to his operation, and led to the beginning of the end for Legs Diamond. The man who may have gotten his nickname for the way he could run for his life ran out of running room. Five months later, someone finally shot this guy “so he don’t bounce back.”

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