Vincent Drucci, also known as "The Schemer", was an American mobster during Chicago's Prohibition era who was a member of the North Side Gang, Al Capone's best known rivals. A friend of Dean O'Banion, Drucci succeeded him by becoming co-leader. He is the only American organized crime boss to have been killed by a policeman.

Alphonse Gabriel Capone, sometimes known by the nickname "Scarface", was an American gangster and businessman who attained notoriety during the Prohibition era as the co-founder and boss of the Chicago Outfit from 1925 to 1931. His seven-year reign as a crime boss ended when he went to prison at the age of 33.