17. Frank "The Enforcer" Nitti
An underling and eventual puppet successor to Al Capone, Nitti ran the Outfit's bootlegging operations, channeling whiskey from Canada into Chicago speakeasies. In The Untouchables, Kevin Costner threw him off a roof, an in other films he has been portrayed by Sylvester Stallone and Stanley Tucci. In reality, he was softer and bureaucratic, pushing the mobsters into polical coercion, extorting money from Hollywood studios. In name he took over for Capone, though others ran the show. His survival is testament. Severe claustrophobia led him to commit suicide in a rail yard rather than face prison.