William Hale Thompson ( May 14 , 1869 -- March 19 , 1944 ) was Mayor of Chicago from 1915 to 1923 and again from 1927 to 1931 .
William Hale Thompson ( May 14 , 1869 -- March 19 , 1944 ) was an American who was the Mayor of Chicago from 1915 to 1923 and again from 1927 to 1931 .