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William Kennedy's Prohibition Story

Master storyteller and Pulitzer Prize-winning author William Kennedy recounts the fascinating and violent exploits of gangster-bootlegger Jack 'Legs' Diamond during the prohibition era.

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Timeline: 'They Can't Kill Legs Diamond'

1897: Jack Diamond is born in New York City to a
poor family of Irish immigrants.

  • December 24, 1913: Jack's mother, Sara,
dies. Jack, who is 16, moves to Brooklyn with his
father and brother, and soon begins racking up
a criminal record of robbery and assault.

  • January 17, 1920: The Eighteenth
Amendment to the Constitution goes into effect,
banning alcohol in the U.S. This law gives rise to
Jack 'Legs' Diamond's illicit liquor empire.

  • August 18, 1923: Diamond pays Louis Kushner to
shoot Nathan Kaplan (a.k.a. 'Kid Dropper'). Kid
Dropper was a leader of the New York criminal world and
his death creates a vacuum in the city's organized crime
arena that Diamond quickly fills. Diamond soon assembles a group of robbers, hijackers and bootleggers, including Charles 'Lucky' Luciano and 'Dutch Shultz.'

  • October 15, 1927: Diamond is shot twice and rushed to Bellevue Hospital in critical condition, where he makes a remarkable recovery.

  • July 13, 1929: Jack 'Legs' Diamond and a partner shoot and kill some men who were causing commotion in Diamond's Hotsy Totsy Club. Though more than fifty people saw the shootings, the police case collapses as witnesses are murdered or intimidated. Diamond retreats to Acra, New York.

  • August 22, 1930: Wanted by the authorities for
questioning related to the murder of Harry Western, a roadhouse owner who played a large role in the distribution of alcohol in Upstate New York, Diamond boards a ship headed for Europe, eventually landing in Germany.

  • October 12, 1930: Upon returning from Europe, Diamond is shot while staying at the Hotel Monticello in New York City, supposedly in revenge for double-crossing fellow gangster Vannie Higgins. Rushed to Polyclinic Hospital in critical condition, Diamond manages to recover yet again and returns to Acra.

  • April 18, 1931: Diamond and his associates hijack a truck containing applejack (a popular alcoholic drink) near Catskill, New York. Diamond seeks information from the truck's driver, Grover Parks, who is tortured but reveals no information. Parks manages to escape to the Catskill police station, leading to warrants for Diamond's arrest.

  • April 27, 1931: While awaiting a call from his lawyer at the Aratoga Inn near Cairo, New York, Diamond is shot, and yet again, he recovers, this time at Albany Hospital. Dr. Thomas Holmes tells reporters that 'The man is a medical wonder.' It is said that Diamond was known to say, 'They can’t kill Legs Diamond,' from time to time.

  • June 2, 1931: A raid on the Barmann Brewery in Kingston, New York uncovers one of the largest beer-making venues in the Northeast, shutting down one of Diamond's most important suppliers.

  • December 13, 1931: Diamond's trial for the kidnapping and torture of Grover Parks, the truck driver, begins. Diamond is acquitted. The Philadelphia Public Ledger writes that Diamond had become a symbol of defiance of an unpopular law.

  • December 17, 1931: After celebrating his acquittal with his mistress, showgirl Kiki Roberts, Diamond returns to the apartment he had been renting on Dove Street in Albany, where he is shot and killed. Who killed Legs Diamond? The case was never officially solved, but the WMHT documentary 'William Kennedy’s Prohibition Story' sheds light on the matter.