Jack "Legs" Diamond (possibly born John Thomas Diamond, though disputed; July 10, 1897 – December 18, 1931), also known as Gentleman Jack, was an Irish American gangster in Philadelphia and New York City during the Prohibition era. A bootlegger and close associate of gambler Arnold Rothstein, Diamond survived a number of attempts on his life between 1916 and 1931, causing him to be known as the "clay pigeon of the underworld". In 1930, Diamond's nemesis Dutch Schultz remarked to his own gang, "Ain't there nobody that can shoot this guy so he don't bounce back?" Early life Diamond was born July 10, 1897, to Sara and John Moran, who emigrated from Ireland in 1891 to Philadelphia, USA. In 1899, Jack's younger brother Eddie Moran was born. Jack and Eddie both struggled through grade school, while Sara suffered from severe arthritis and other health problems. Sara passed away on December 24, 1913, following complications brought on by a bacterial infection and a high fever. John Moran moved to Brooklyn shortly afterwards. Diamond soon joined a New York street gang called the Hudson Dusters. Diamond's first arrest for burglary occurred when he broke into a jewelry store on February 4, 1914. Diamond served in the US Army in World War I but deserted in 1918 or 1919 and was convicted and jailed for desertion. He served two years of a three- to five-year sentence at Leavenworth Military Prison and after being released in 1921 Diamond became a thug and later personal bodyguard for Arnold Rothstein. Lifestyle Diamond was known for leading a rather flamboyant lifestyle. He was an energetic individual—his nickname "Legs" derived either from his being a good dancer or from how fast he could escape his enemies. His wife, Alice, was never supportive of his lifestyle but did not do much to dissuade him from it. Diamond was a womanizer; his best known mistress was showgirl and dancer Marion "Kiki" Roberts. Prohibition and the Manhattan Bootleg Wars In the late 1920s Prohibition was in force, and the sale of beer and other alcohol was illegal in the United States. Diamond traveled to Europe to acquire beer and narcotics but failed. He did obtain liquor, which was dumped overboard in partially full barrels that floated onto Long Island as ships entered New York. He paid children a nickel for every barrel they brought to his trucks. Following the death of Jacob