Alphonse Capone was one of the most famous U. S. gangsters during the 1930s, a Chicago-based boss involved in illegal gambling, bootlegging (illegal alcohol) and prostitution. Capone got his start in New York, working as a thug and bouncer (where he got the three scars that spawned his nickname, "Scarface"). He moved to Chicago in 1919 and quickly moved up in the ranks of Johnny Torrio's gang. Capone was known for his smarts and brutality, and by 1925 he was in charge of one of Chicago's biggest criminal gangs. It was Capone's men who gunned down seven rivals in 1929 in what was called the "St. Valentine's Day Massacre." Arrested many times over the years, Capone was famously pursued by federal agent Eliot Ness and ended up finally going to jail for income tax evasion in 1931. After serving eight years in federal prisons, Capone was released on good behavior and because he'd been suffering from syphilis-related ailments. Capone retired to his estate in Florida and died in 1947 of heart failure.

Extra credit: Capone has been portrayed in the movies by by Rod Steiger (Al Capone, 1959), Neville Brand (TV's The Untouchables, 1959-63), Robert DeNiro (The Untouchables, 1987) and William Forsythe (TV's The Untouchables, 1993).