Born to an Irish immigrant family on July 10, 1897, in Philadelphia, Diamond becomes a leading figure in organized crime during the Prohibition era. He establishes liquor-smuggling enterprises in New York City and upstate New York, where he lives for a time after shooting and killing men in his Hotsy Totsy club.
After his mother’s death, Diamond moves with his father and brother to Brooklyn, New York. Growing up impoverished, he turns to street gangs and becomes involved in theft and violent crime as a teen. He later begins to work for gangsters Arnold Rothstein and Jacob “Little Augie” Orgen.
The Prohibition era begins in 1920. With alcohol smuggling a profitable underworld enterprise, Diamond organizes truck heists to seize liquor for his speakeasies. In 1923, he orders the murder of mob boss Nathan “Kid Dropper” Kaplan and usurps 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.
Diamond sets up shop as an extremely violent and murderous figure. He earns his “Legs” nickname either due to his quickness when running from a scene of larceny or because of his prodigious dancing skills. He also marries Alice Schiffer in 1926. She remains devoted to him through his strings of crime and mistresses, which includes a notable affair with Ziegfeld Follies showgirl Kiki Roberts.
After a 1929 incident where Diamond publicly kills men in his Hotsy Totsy nightclub, authorities are unable to make the case stick due to the harassment and murder of witnesses. Looking to lie low, Diamond moves to Acra in upstate New York, where he sets up a huge beer-smuggling business.
During the course of his mob career, Diamond is shot on many occasions, receiving hospital treatment and recovering each time, earning the nickname “Clay Pigeon.”
In April 1931, near Catskill, New York, Diamond and colleagues hijack a truck with applejack liquor driven by Gordon Parks, whom they kidnap and torture. Parks survives and manages to reach the police. Diamond is arrested for the attack but later is acquitted in a December trial.
Diamond celebrates his acquittal days later with Roberts and returns drunk to his Albany residence. Early that morning, on December 18, 1931, he is shot and killed. He is buried at Mt. Olivet Cemetery in Maspeth, Queens on December 23. There is no church service or graveside ceremony. Two hundred family and spectators attend Diamond’s interment, however no criminal figures are spotted.
The mystery remains as to who is behind the killing. Biographer William Kennedy speculates 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.
On July 1, 1933, Diamond’s widow, Alice Kenny Diamond, is found shot to death in her Brooklyn apartment. It is speculated that she is shot by Diamond’s enemies to keep her quiet.
(From: “Jack ‘Legs’ Diamond Biography” by the Editors of Biography.com, April 2, 2014)