Al Capone
Al Capone aka “Scarface,” is the most infamous gangster in American history. He ran the “Chicago Outfit,” a multimillion-dollar branch of the Mafia that ran bootlegging, prostitution and gambling rackets in the 1920’s and ‘30’s. He was also tied to hundreds of murders including the St. Valentine’s Day Massacre, in 1929, that left 7 of his shot in the back, execution-style. Capone was never jailed for his racketeering or his brutality but he was convicted of income-tax evasion and jailed in Alcatraz where he became one of the highest profile prisoners ever to serve time on “The Rock.” Although Capone never tried to escape from Alcatraz, 36 other prisoners did and 3 may have been successful.