Al Capone

Born in New York City in 1899 to Italian immigrants, Alphonse Gabriel Capone joined the Five Points Gang as a teenager and worked as a bouncer in brothels before moving to Chicago in his early twenties. He became bodyguard to Johnny Torrio, head of a syndicate smuggling illegal alcohol, and took over in 1925 after North Side gunmen nearly killed his boss. For seven years Capone expanded the bootlegging operation through escalating violence while enjoying protection from Mayor William Hale Thompson and the Chicago Police Department. He played to crowds - cheering at baseball games, donating to charities, cultivating a Robin Hood image - until the Saint Valentine's Day Massacre in broad daylight turned him into "Public Enemy No. 1" and forced Washington's hand. Federal authorities charged him with twenty-two counts of tax evasion in 1931; he was convicted of five and sentenced to eleven years. Neurosyphilis surfaced early in his sentence, and he left prison after almost eight years increasingly debilitated, dying of cardiac arrest after a stroke in 1947 at age forty-eight.