Chicago in the 1930s 5,000 "Prohibition" violations that could have "nailed him" for 25,000-years-to-life if convicted on all the charges. And, it has been said that Capone underling Gus Winkler was prevented by other Capone men from freeing him outright, with $100,000 upfront (a tax payment, not a bribe) to the federal taxman. On 24 October 1931, one week after he was convicted of tax evasion, Al Capone was sentenced to 11 years in federal prison (first, Atlanta Federal Penitentiary, then Alcatraz Island), fined $50,000 and charged $30,000 in court costs. While awaiting transfer to Atlanta to serve his sentence, Capone sat in Cook
Al Capone and the Bowery Boys. He then joined the Brooklyn Rippers, and then the powerful Five Points Gang based in Lower Manhattan. During this time, he was employed and mentored by fellow racketeer Frankie Yale, a bartender in a Coney Island dance hall and saloon called the Harvard Inn. Capone inadvertently insulted a woman while working the door at a Brooklyn night club and was slashed by her brother Frank Gallucio. The wounds led to the nickname "Scarface" which Capone loathed. When he was photographed, he hid the scarred left side of his face, saying that the injuries were war wounds.