William Hale Thompson was an American politician who served as mayor of Chicago from 1915 to 1923 and again from 1927 to 1931. Known as "Big Bill", he is the most recent Republican to have served as mayor of Chicago. Historians rank him among the most unethical mayors in American history, mainly for his open alliance with Al Capone. However, others recognize the effectiveness of his political methods and publicity-oriented campaigning, acknowledging him as a "Political Chameleon" and an effective political machine.

Frederick Lundin was a U.S. Representative from Illinois and a Republican Party ward boss in Chicago. He played an instrumental role in the successful mayoral elections of William Hale Thompson and the creation of Thompson's patronage system. He also built up the organized syndicate later taken over by Al Capone in 1922.