McCaskey became the Chief Executive Officer and President of the Bears in 1983, succeeding his grandfather George Halas in the role. He was voted the Executive of the Year after the 1985 season, during which Chicago won the Super Bowl. He is just one of four individuals to hold the office in the organization’s history.
The oldest son of Bears owner Virginia Halas McCaskey, he retained a key role in football operations within the organization until 1999, when he was replaced by the current CEO and President of the franchise, Ted Phillips. Controversial decisions, such as his firing of longtime head coach Mike Ditka after the 1992 season, plagued the later years of his tenure after achieving early success. McCaskey then took on the position of chairman until he stepped down in 2011. His younger brother George succeeded him in the role.
“Mike was already successful in every sense of the word when he took over for George S. Halas after the passing of ‘Papa Bear’ in 1983”, the McCaskey family stated in the announcement. “We are grateful to Mike for overseeing arguably the greatest team in NFL history, and for his many years of service to the Bears and to us. The oldest of eleven siblings has many duties thrust upon them, not all of them pleasant, yet Mike handled them all with grace and patience.”
McCaskey is survived by his wife Nancy, their two children John and Kathryn, and numerous other relatives.