Legs Diamond, The Bootlegger Who Wouldn’t Die
What was Legs Diamond famous for? Rival gangsters couldn’t figure out how to kill him.
Bootleggers worked in a dangerous business. But Jack “Legs” Diamond was up to the task — gunmen shot Diamond four times and he survived.
One rival even complained, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”
Legs Diamond operated during Prohibition, when the federal government banned alcohol. A bootlegger and a gangster, Diamond had his hand in speakeasies and racketeering. He made a lot of enemies who tried — but failed — to kill him. But eventually, Diamond’s luck ran out.
From Hudson Duster to Dancing Bootlegger
Even before Prohibition, Legs Diamond had a rap sheet. As a teenager, Diamond joined the Hudson Dusters, a gang in Manhattan. The gangster’s first arrest came at 16 when he broke into a jewelry store.
Diamond took a break from crime to fight for the U.S. Army in World War I, but then deserted, landing him in jail for two years.
After his prison sentence, Diamond took a job working for crime boss Arnold Rothstein. Soon, Prohibition drove Diamond into bootlegging, where he came up with a scheme to float barrels of beer in New York Harbor and pay children a nickel for delivering the barrels to him.
Why was he called “Legs” Diamond? Diamond loved dancing and his girlfriends included showgirl Marion “Kiki” Roberts. But some claim the nickname came from Diamond’s ability to outrun death.
The Gangster with Nine Lives
The Hotsy Totsy Club was a prime destination for gangsters in 1920s Manhattan. And part-owner Legs Diamond funneled alcohol into the club. Running with a rough crowd put Diamond in the line of fire.
In 1924, Diamond tried to swipe liquor from a rival gang and walked away with shotgun pellets in his face. A few years later, mob bosses sent thugs to shoot Diamond on the street, but he survived two gunshots to his chest.
Diamond’s closest brush with death came in 1930. In the middle of the night, two gunmen broke into Diamond’s hotel room and shot him five times. But Diamond didn’t die. Instead, he tossed back two shots of whiskey and dragged himself into the hall. The bootlegger ended up in the hospital but walked out on his own two feet.
One year later, gunmen burst into an inn dining room and shot Diamond three times. Yet again, Diamond survived. At the hospital, Diamond bragged, “they have not yet made the bullet that will kill me.”
How did Legs Diamond die?
Death finally caught up with Legs in 1931. This time, the gunmen who broke into Diamond’s hotel room held him down and shot him in the head three times to make sure Diamond died.
The murder remains unsolved.
For more strange and fascinating stories from history, check out Bruce Wilson’s book Strange but True Stories: Fascinating Facts, Astonishing Trivia, and Conversation Starters from History, available in ebook, paperback, or audiobook.
Bruce Wilson Jr. is the author of nine books on history. Visit Bruce Wilson’s website to learn more.
