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Owney Madden bootlegger and owner of the Cotton Club: rumored to be Mae West's lover and chief financial backer for her show "Sex"

Owney Madden, once public enemy No. 1 as a gang leader in New York's Hell's Kitchen (the "Westies"), leaves the district attorney's office in New York City after testifying before a grand jury. Madden, having retired to Hot Springs, Arkansas, returned to face the probe, which was trying to determine the reason for his being on a coal company's payroll at $50 a week. Photographed: July 20, 1934

Al Capone was probably the most famous organized crime lord, or more commonly known as a gangster, in American history. Organized crime really started to boom in the 1920's because of Prohibition and other factors.

Jack Johnson. In 1920, Johnson opened a night club in Harlem; he sold it three years later to a gangster, Owney Madden, who renamed it the Cotton Club.

Cotton Club poster: The Cotton Club was a New York City night club located first in the Harlem neighborhood and then in the midtown Theater District. The club operated from 1923 to 1940, most notably during America's Prohibition Era. The club was a whites-only establishment even though it featured many of the best black entertainers and jazz musicians.

The Gophers: Hell’s Kitchen’s most brutal gang. Owney Madden, fourth from left in this 1910 gang photo, earned a rep as one of the most brutal Gopher leaders. Nicknamed The Killer, he’s responsible for numerous deaths of other gang members, especially from the rival Hudson Dusters. After serving time in Sing Sing, he became a bootlegger and co-owner the Cotton Club, Harlem’s flashy club in the 1920s.

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New Lawless Infographics Breakdown Bootleggers And The Bad Girls of Prohibition

Gangsters of prohibition I choose this pic because it shows the top bootleggers of the 1920s

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Last of the Cotton Club girls: Legendary dancer who starred at Harlem's notorious 'whites-only' venue dies aged 100

The Cotton Club, New York - which was run by the gangster Dutch Schultz was open from 1923 to 1940 - notably through the Prohibition Era.