born: May 14, 1869, Boston, Massachusetts died: March 18, 1944 Mayoral Terms: 1915-1923 & 1927-1931
Big Bill Thompson was the last Republican to serve as mayor of Chicago. Upon Thompson's death, two safe deposit boxes in his name were discovered to contain nearly $1.5 million in cash. Thompson was born in Boston, but his family moved to Chicago when he was only nine days old. Instead of college, he traveled in Europe and then took up ranching in Texas and New Mexico, returning to Chicago in 1892 after his father's death. Early in his political career, Thompson began to amass a war chest to support an eventual run for the Presidency by charging city drivers and inspectors $3 per month. After being defeated in 1923, Big Bill organized a "scientific" expedition to search for tree-climbing fish in the South Seas. In 1927, Al Capone's support of Thompson allowed the man to return to the mayor's office. Pledging to clean up Chicago and remove the crooks, Thompson turned his attention to the reformers, who he saw as the real criminals. According to Thompson, at this time the biggest enemy the United States had was King George V of England. Thompson promised his supporters that if they ever met, Thompson would punch the King in the nose. During this final term in office, the "Pineapple Primary" occurred (April 10, 1928), so called because of the bombs used to intimidate politicans. The St. Valentine's Day Massacre also took place while Thompson was mayor.