Location of crimes: New York City and abroad. Gentleman Jack, also known as “Legs Diamond” was a name that continues to live on in fame. He was a well known bootlegger of the prohibition era. During the 1920’s he would pay children a nickel for every barrel they could retrieve from the Long Island coast. Many fellow gangsters tried to murder Diamond throughout the Irishman’s life, but they didn’t get him until the early 1930’s while he was asleep in a rooming house in Albany.