In 1936, Berwanger became the first player to be drafted by the National Football League (NFL) in its inaugural draft. The Philadelphia Eagles selected him but did not think they would be able to meet his reported salary demands of $1,000 per game. They traded his negotiating rights to the Chicago Bears for tackle Art Buss. Berwanger initially chose not to sign with the Bears in part to preserve his amateur status so that he could compete for a spot on the U.S. team for the 1936 Summer Olympics in the decathlon.
After he missed the Olympics cut, Berwanger and Bears' owner George Halas were unable to reach an agreement on salary; Berwanger was requesting $15,000 and Halas' final offer was $13,500. Instead, he took a job with a Chicago rubber company and also became a part-time coach at his alma mater. Berwanger later expressed regret that he did not accept Halas' offer.
After graduating, Berwanger worked briefly as a sportswriter and later became a manufacturer of plastic car parts. He was very modest about the Heisman and used the trophy as a doorstop in his library. The trophy was later bequeathed to the University of Chicago Athletic Hall of Fame, where it is on display. There is also a replica of the Heisman on display in the trophy case in the Nora Gymnasium at Dubuque Senior High School. He is a member of both the Iowa Sports Hall of Fame and Chicagoland Sports Hall of Fame.