Turn Up the Jazz: Murder and Mayhem in Prohibition New York City

Dirty, Sexy History

drag_ball_in_webster_hall-1920s

It was July 1929, and ex-convict Simon Walker walked into a speakeasy. He came with friends William “Red” Cassidy and Peter Cassidy, a couple of guys known as waterfront street fighters, and the bar was the Hotsy-Totsy Club at Broadway and Fifty-fourth Street. The speakeasy was owned by the gangster, Jack “Legs” Diamond, and his partner, Charles Entratta. Alcohol mixed with high tensions resulted in an argument between the Cassidy boys and Legs. Guns were drawn and shooting commenced. The orchestra played on, covering up the sounds of gunfire as Simon Walker was killed.

The murder of Simon Walker in the Hotsy-Totsy Club in 1929 was a common occurrence in the Prohibition days of New York City. Bootlegged liquor, speakeasies, and gangsters ruled the city, and the changing ideas of sexuality, class structure, and views on drinking turned the city upside down.

jackdiamond Jack “Legs” Diamond

The Volstead Act went into…

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