Thompson for Mayor

William Hale Thompson (May 14, 1869 – March 19, 1944), known as “Big Bill,” was a Republican and the mayor of Chicago from 1915-1923 and 1927-1931. Thompson was born in Boston, but his family soon moved to Chicago. The nickname “Big Bill” was not just for his more than six-foot height but for his flamboyant personality. He worked as a cowboy when he was young and styled himself as a cowboy for much of his career, his hat becoming a symbol for his campaigns. Thompson was a pioneer of publicity-oriented, exaggerated campaigns that often featured uncensored language.  

Thompson is also known as the most corrupt official in Illinois history. In 1927, Prohibition and the Chicago gang wars were at their peak, and Thompson was associated with Al Capone. Capone funneled at least $100,000 to Thompson’s 1927 campaign, and Big Bill appointed a Capone agent, Daniel Serritella, as a city sealer to keep an eye on City Hall. Capone also set up gambling operations a block from City Hall and bribed many city officials. In 1931, Thompson lost his reelection bid to Anton Cermak. In 1936, Big Bill made a failed attempt to the Governorship, and in 1939, attempted (and lost) one last run in Chicago's mayoral election. Despite his corruption, Thompson was a popular politician during his career, however that popularity collapsed when over $2 million worth of assets were found in four security boxes, revealing the true extent of his nefariousness.