Upon graduating from the University of Pennsylvania, McCaskey served in the 80th Division of the United States Army during World War II for two-and-a-half years.

The older Halas expressed his doubts about McCaskey, so he sent two "agents", Bert Bell and Art Rooney, owners of the Philadelphia Eagles and Pittsburgh Steelers, respectively, to inspect him.

[3] In 1999, McCaskey relinquished his position as chairman of the board to Michael, who was promoted after various incidents occurred such as the botched hiring of Dave Wannstedt's replacement and failed attempt to get a new stadium.

On April 8, 2003, McCaskey died in his Des Plaines, Illinois home; he had been in declining health, and was survived by his wife and eleven children.

[5] McCaskey left a lasting impact on the Bears, such as befriending Brian Piccolo, and placing him with Gale Sayers in the same room, making them the first interracial roommates.