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 arrival at Atlanta, the Capone was officially diagnosed with syphilis and gonorrhoea. He was also suffering from withdrawal symptoms from cocaine addiction, the use of which had perforated his nasal septum. Capone was competent at his prison job of stitching soles on shoes for eight hours a day, but his letters were barely coherent. He was seen as a weak personality, and so out of his depth dealing with bullying fellow inmates that his cellmate, seasoned convict Red Rudensky, feared that Capone would have a breakdown. Rudensky was formerly a small-time criminal associated with the Capone gang, and found himself