Jack “Legs” Diamond was born on July 10, 1897 in Philadelphia, Pennsylvania. He came from an immigrant Irish family. When his mother, Sara, died in 1913 he moved to Brooklyn, New York with his father and his little brother. Because his father left him unsupervised and underfed, Diamond began associating with local gangs in New York. He associated with well known gangsters like Arnold Rothstein and Jacob Orgen. He was known to commit theft and violent crimes until 1920.
In the 1920s Prohibition era began and marked a significant opportunity for organized crime. Around this time, Diamond began his profitable career in alcohol smuggling. He would organize truck heists to retrieve liquor for his privately owned speakeasies, eventually advancing to the position of organized crime boss shortly after he ordered the murder of Nathan Kaplan.
Diamond was married in 1926 to a woman named Alice Schiffner, who remained loyal to him even with his well known criminal activities and mistresses. People who knew Diamond, including his wife, described him as extremely violent and murderous. In 1929 Diamond publicly killed men is his night club, but authorities could not make the charges stick because of the harassment and murder of key witnesses by Diamond and his crew.
Diamond later moved to Acra, New York to lay low. There he began a large beer smuggling business. Diamond participated in heists with his crew and was often shot. He managed to survive many bullet wounds which granted him the nickname “clay pigeon.” In 1931 Diamond was arrested for the kidnapping and torture of Gordon Parks. On December 18, 1931 Diamond was acquitted and went home to celebrate. He was murdered that night in his home. Many speculate that either police officers or rival gangs are the ones who finally killed Jack Diamond, but a year and a half later his wife was also murdered in their home.