Chicago Bears

Virginia Halas McCaskey, the daughter of franchise founder George Halas, has served as the principal owner of the Chicago Bears since her father's death in 1983. Now over 100 years old, she is the oldest owner in NFL history and remains deeply revered as the living link to the franchise's founding. Under her stewardship, the Bears won Super Bowl XX and maintained their status as one of the league's iconic franchises, though the team has struggled to find sustained on-field success in recent decades.

George McCaskey, Virginia's son, has served as the Bears' chairman of the board since 2011, handling the day-to-day oversight of the franchise. He has overseen multiple coaching and front office changes, including the hiring of general manager Ryan Poles and the franchise's ambitious rebuild around quarterback Caleb Williams. McCaskey has been a polarizing figure among the fan base — some appreciate his steady hand, while others have criticized the organization's inability to sustain winning under his leadership.

The McCaskey family collectively owns the Chicago Bears, with various descendants of George Halas holding stakes in the franchise. The family ownership structure has provided continuity — the Bears are one of the few NFL franchises that have never been sold — but has also been a source of frustration for fans who have watched wealthier, more aggressive ownership groups invest heavily in their teams.