Jack "Legs" Diamond Biography

Murderer, Organized Crime (1897–1931)
Jack "Legs" Diamond was a Prohibition-era mob leader, hit man and bootlegger who was based in New York.


Born on July 10, 1897, in Philadelphia, Jack "Legs" Diamond became a leading figure in organized crime during the Prohibition era. He established liquor-smuggling enterprises in New York City and upstate New York, where he lived for a time after shooting and killing men in his Hotsy Totsy club. He was found dead in 1931 at his home in Albany, New York, after being acquitted of torture.

Crime and Prohibition

Jack "Legs" Diamond was born Jack Moran on July 10, 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.

The Prohibition era began in 1920. With alcohol smuggling a profitable underworld enterprise, Diamond organized truck heists to seize liquor for his speakeasies. In 1923, Diamond ordered the murder of mob boss Nathan "Kid Dropper" Kaplan and usurped power in the world of organized crime for himself, aligning himself with mobsters like Lucky Luciano and Dutch Schultz. (Diamond and Schultz would later become rivals.)

A Murderous Figure

Diamond 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 of larceny or because of his prodigious dancing skills. He also married Alice Schiffer in 1926. She remained devoted to Diamond through his strings of crime and mistresses, which included a notable affair with Ziegfeld showgirl Kiki Roberts.

After a 1929 incident where Diamond publicly killed men in his Hotsy Totsy nightclub, authorities were unable to make the case stick due to the harassment and murder of witnesses. Looking to lie low, Diamond moved to Acra in upstate New York, where he set up a huge beer-smuggling business.

During the course of his mob career, Diamond was shot on many occasions, receiving hospital treatment and recovering each time, earning the nickname "Clay Pigeon."

End of Diamond's Career

In April 1931, near Catskill, New York, Diamond and colleagues hijacked a truck with applejack liquor driven by Gordon Parks, whom they kidnapped and tortured. Parks survived and managed to reach the police. Diamond was arrested for the attack but later was acquitted in a December trial.

Diamond celebrated his acquittal days later with Roberts and returned drunk to his Albany residence. Early that morning, on December 18, 1931, Diamond was shot and killed. The mystery remains as to who was behind the killing. Biographer William Kennedy speculated that Diamond was taken out by Albany police via an order from political leader Dan O'Connell. Others say rival gangsters were behind the murder. Diamond's widow was also found murdered in her home a year and a half later.

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