Vote
Born in Brooklyn, New York, to Neapolitan emigrants Gabriele and Teresina Capone, he began his career in Brooklyn before moving to Chicago and becoming the boss of the criminal organization known as the Chicago Outfit.
Votes:
973
Al Capone
55.2%
Vote
Sinatra has been frequently linked to members of the Mafia and it has long been rumored that his career was aided behind the scenes by organized crime.
Votes:
789
Frank Sinatra
44.8%