Al Capone
It seemed as if law enforcement couldn't touch him. The most powerful mobster of his time, Al Capone ruled an empire of crime, known as the Chicago Outfit. And as much as authorities would have liked to nab him on charges of gambling, prostitution, bootlegging, bribery, narcotics trafficking, robbery, "protection" rackets or murder, they had to settle for tax evasion and the lighter sentence that went along with it. On October 24, 1931, Capone was sentenced to 11 years in federal prison, fined $50,000 and charged $7,692 for court costs, in addition to the $215,000 (plus interest) he owed in back taxes. Though authorities worked hard for many years to bring Capone in, they let him go early. He was paroled November 16, 1939. One of the most notorious crooks of all time served just seven years, six months and fifteen days behind bars.