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FAQs
Sinatra continued to associate with mob figures throughout the years (“If you sing in joints, you're gonna know the guys that run them,” was Sinatra's standard defense), but his association with Giancana was perhaps the most publicized.
Al Capone was a Chicago crime boss notorious during the prohibition era. He was known for always wearing a fedora hat, a loud tie and never leaving the house without his bodyguards. The above photo is a rare picture of the mobster taken at a football game in Chicago in 1931.
Al Capone. Al “Scarface” Capone is most commonly associated with Prohibition-era Chicago, where he rose to prominence running bootlegging, prostitution, and gambling operations, but the mob boss traded in the harsh Illinois winters for a Miami Beach manse in 1928.
John Handsome Johnny Roselli (born Filippo Sacco; July 4, 1905 – August 7, 1976), sometimes spelled Rosselli, was a mobster for the Chicago Outfit who helped that organization exert influence over Hollywood and the Las Vegas Strip.
And many mob bosses really did appreciate jazz. “[Al] Capone was the greatest benefactor.