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Independent Press Award

2024 Distinguished Favorite

Gangsterland: A Tour Through the Dark Heart of Jazz-Age New York City

David Pietrusza


A site by site, crime by crime, outlaw by outlaw walking tour through the seedy underbelly of Roaring Twenties Manhattan—where gamblers and gangsters, crooks and cops, showgirls and speakeasies ruled the day and, always, the night.

In Gangsterland, historian David Pietrusza tours the Big Apple’s rotten core. The Roaring Twenties blaze and sparkle with Times Square’s bright lights and showgirls, but its dark shadows mask a web of notorious gangsters ruling New York City. At the heart of this wickedness nests a “Prince of Darkness,” Arnold Rothstein, the kingpin most noted for fixing baseball’s infamous 1919 World Series, who also bankrolled high-stakes gambling dens, speakeasies, trigger-happy bootleggers, and even a record setting Broadway show.

Sharing center stage are con artists Nicky Arnstein and “Dapper Don” Collins; crooked cop Lt. Charles Becker; politicians Mayor “Gentleman Jimmy” Walker and “Big Tim” Sullivan; master drug smugglers George Uffner and Sidney Stajer; murderous racketeers Lucky Luciano and Legs Diamon; show biz legends Flo Ziegfeld, Fanny Brice, and Texas Guinan; and many more. As Pietrusza prowls city boulevards and back alleys, exposing Tammany Hall, sports, Broadway, and Wall Street, jewels are fenced, bullets fly, and unmarked bills buy bribes and silence.

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