Jack Diamond

Gangster bootlegger. Born Jack Moran on July, 1897, in Philadelphia, Pennsylvania, to an Irish immigrant family. After his mother, Sara’s death, Diamond moved with his father and brother to Brooklyn, New York. Growing up impoverished, Diamond turned to street gangs and became involved in theft and violent crime as a teen. He later began to work for gangsters Arnold Rothstein and Jacob “Little Augie” Orgen. Jack set up shop as an extremely violent and murderous figure. He earned his “Legs” nickname either due to his quickness when running from a scene or because of his excellent dancing skills. He also married Alice Schiffer in 1926. She remained devoted to Jack through his strings of crime and mistresses, which included a notable affair with Ziegfeld showgirl Kiki Roberts. In August, 1927, Jack played a role in the murder of “Little Augie” (Jacob Orgen). Jack’s brother Eddie was Orgen’s bodyguard, but Legs Diamond substituted for Eddie that day. As Orgen and Jack were walking down a street on the Lower East Side of Manhattan, three young men approached them and started shooting. Orgen was fatally wounded and Jack was shot two times below the heart. He was taken to Bellevue Hospital, where he eventually recovered. During the late 1920s, Prohibition was in force, and the sale of beer and other alcohol was illegal in the United States. Jack traveled to Europe to score beer and narcotics, but failed. He did score liquor which was dumped overboard in partially full barrels which floated into Long Island as ships entered New York. Following Orgen’s death, Jack went to work overseeing bootleg alcohol sales in downtown Manhattan. That brought him into conflict with Dutch Schultz, who wanted to move beyond his base in Harlem. He also ran into trouble with other gangs in the city. In 1930, Jack and two henchmen kidnapped Grover Parks, a truck driver in Cairo, New York, and demanded to know where he had obtained his load of hard cider. When Parks denied carrying anything, Jack and his men beat and tortured Parks, eventually letting him go. A few months later, Jack was charged with the kidnapping of James Duncan. He was sent to Catskill, New York for his first trial, but was acquitted. However, he was convicted in a federal case on related charges, and he was sentenced to four years in jail. In a third trial, in Troy, New York, he was acquitted. On October 12, 1930, Jack was shot and wounded at the Hotel Monticello on the west side of Manhattan. Two men forced their way into his room, shot him five times, and then fled. Still in his pajamas, he staggered out into the hallway and collapsed. On December 30, 1930, Jack was discharged from Polyclinic. On April 27, 1931, Jack was again shot and wounded, this time at the Aratoga Inn, a road house near Cairo, New York. He was eating in the dining room with three companions when he walked out to the front door. A gunman with a shotgun shot him three times, and Jack collapsed by the door. On December 18, 1931, Jack’s enemies finally caught up with him, At 4:30 am, Jack went back to the rooming house and passed out on his bed. Two gunmen entered his room around 5:30 AM. One man held Jack down while the other shot him three times in the back of the head. No other gangster of the bootlegging era of 1920’s survived more bullet wounds than Legs. He was known as “The Clay Pidgeon of the Underworld”. On July 1, 1933, Jack’s widow, Alice Kenny Diamond, was found shot to death in her Brooklyn apartment. It was speculated that she was shot by Jack’s enemies to keep her quiet.