A successful businessman in Chicago, Illinois, Bidwill was also vice president of the Chicago Bears. His wealth helped Bears owner George Halas keep the team in 1932. A year later, with Halas' encouragement, he bought the Cardinals from then-owner David Jones.
Despite Bidwill's wealth and enthusiasm, the Cardinals found the going difficult both on and off the field for most of his tenure as owner. In addition to the Depression, they had the misfortune of sharing Chicago with the powerful Bears. World War II decimated the Cardinals' roster, forcing them to merge with the equally strapped Pittsburgh Steelers for the 1944 NFL season.
The end of the war brought another problem when the upstart AAFC placed a team in Chicago, the Rockets. However, Bidwill stunned the football world in 1947 when he outbid the Rockets for the rights to All-American Charley Trippi, signing him to a then unprecedented $100,000 contract. Trippi was the final piece of what Bidwill called his "Dream Backfield" of Paul Christman, Pat Harder, Marshall Goldberg, and Trippi. The quartet led the Cardinals to their first uncontested NFL championship in 1947, but Bidwill was not around to see it; he had died shortly after bagging Trippi.