McCaskey also worked in television after graduating with a bachelor's degree (1978) from Arizona State University and a Juris Doctor[3] degree (1981) from Arizona State University College of Law, and was a reporter for an NBC affiliate in Peoria.

[6] In 2011, during the NFL lockout, McCaskey's brother Michael retired as chairman of the club after 12 years.

[2] With his mother's death,[7] McCaskey is now, as of 2025, the highest figure in the Bears organization, with team president and CEO Kevin Warren reporting to him.

[8] While the president oversees structural changes such as hiring and firing the general manager, the ownership provides input; McCaskey explained in 2012, shortly after the departure of general manager Jerry Angelo, that he did not "feel any particular need to place a personal stamp on the Bears, that my job was to work with and in support of the president and CEO.

[11][12] McCaskey also volunteers as a referee and umpire for Illinois high school sports in Sycamore.