Legs Diamond Finally Dies

December 18, 1931 - Jack "Legs" Diamond, one of the most notorious gangsters of the prohibition era, was murdered on this day. Diamond had survived at least 3 previous attempts on his life.

His criminal career began when he was a teen living in Brooklyn. He ran with a street gang that burglarized stores and apartments in the city. During World War I he served briefly in the Army, but he went AWOL and served jail time for desertion.

The nickname "Legs" was probably related to his knack for always being able to hightail it out of sticky situations.

In the 1920s Diamond ran bootlegging operations for Arnold Rothstein, and he quickly earned a reputation for being a ruthless backstabber. By double-crossing friends and foes alike, Diamond created a world of enemies. One brush with death came while working as a bodyguard for Jacob "Little Augie" Orgen. A drive-by shooting gunned down Orgen, and Diamond took two bullets to the chest. Diamond recovered, but it was rumored that he was in on the conspiracy to kill Orgen, which only added to his slippery reputation.

In 1930 Diamond was ambushed in Manhattan's Hotel Monticello by hitmen from rival Dutch Schultz's gang. They shot Diamond five times. Miraculously, he again managed to survive. Legend has it that after being riddled with bullets, he took 2 whiskey shots and walked out of the room on his own.

Less than six months later, Diamond was dining in a Catskills roadhouse when an assassin blasted him three times with a shotgun. True to form, Diamond would eventually recover from his wounds and get back to work as a bootlegger.  

All the shootings and notoriety had turned "Legs" Diamond into a national celebrity. He bragged about being invincible but his days were numbered.

On the evening of December 18, 1931, Diamond was celebrating his acquittal on a kidnapping charge. When he finally passed out in his bed, a couple of hitmen moved in. They shot him three times in the back of his head. This time he didn't bounce back.

Jack "Legs" Diamond was buried in Mount Olivet Cemetery in Queens.