He was a ruthless, un-loyal, double crosser and the public loved him. Jack “Legs” Diamond bounced back from four attempts on his life and two kidnap trials before a pair of hitmen managed to end his career with three well placed bullets in his head. Jack became one of the premier loft robbers in New York City. By the mid ‘20’s he was working for Arnold Rothstein and hi-jacking liquor trucks in his spare time. This hobby, though lucrative, led to the first known attempt on in life in 1925.
Rothstein introduced Legs to both the narcotics trade as well as Lower Eastside gangster Little Augie Orgen. Both of these introductions would result to trips to the hospital for Legs for bullet removal. By 1930 Diamond’s speakeasy career was washed up in NYC so he set up bootlegging operations in the Catskills.
Diamond then left for Europe to set up a drug trafficking network but he was forced back to the U.S. empty handed. This led to the third attempt on his life in the fall of 1930. Released from the hospital, Diamond returned to the Catskills to concentrate on his liquor trade only to be shot again in the spring of 1931. When he left the hospital he faced a number of trials. After one trial two gunmen snuck into his room at the boarding house where Legs was staying. Diamond had been drinking heavily. After dozing off, the two gunmen fired into his head at close range, making sure that he wouldn’t bounce back again.