He only lost one election in his life, a 1946 contest for Cook County Sheriff. He would go on to win election to his most famous post 6 times. During his tenure, his city saw 
He only lost one election in his life, a 1946 contest for Cook County Sheriff. He would go on to win election to his most famous post 6 times. During his tenure, his city saw unprecedented growth, breaking ground on O'Hare Airport and the Sears Tower. For ten points, who was this man behind the Democratic Machine, longtime mayor of Chicago?
He only lost one election in his life, a 1946 contest for Cook County Sheriff.
{R}ichard {J}. {Daley} or {Daley Sr.} or {Daley I} (prompt on Daley or Richard Daley)