Once a distant figurehead, George McCaskey has earned back Bears fans by leading with emotion, investment, and a willingness to feel every win and loss alongside them.
The Chicago Bears are lucky to have George McCaskey as their owner.
But it didn’t always feel that way.
For a long time, McCaskey was viewed by much of the fanbase as more of a figurehead than a true decision-maker. While his mother, Virginia McCaskey, was still calling the shots, George often became the public face attached to an organization that struggled with consistency, direction, and credibility. Fair or not, he absorbed frustration that had been building for years.
That perception has changed — and not by accident.
As McCaskey gained more autonomy and freedom to run the organization his way, Bears fans began to see a different side of him. One that feels far more emotional, engaged, and genuinely invested in the same moments that define fandom in Chicago.
That shift has shown up repeatedly.
Before one of the Bears’ regular-season matchups against the Green Bay Packers, McCaskey was seen taking photos with fans tailgating outside the stadium. When a Packers fan attempted to photobomb one of the pictures, McCaskey reacted instinctively — visibly annoyed, stiff-arming the fan out of frame in a moment that quickly went viral. The Packers fan looked confused at first, only realizing seconds later that he had just been pushed aside by the Bears’ owner himself.
It was funny. But it was also telling.
McCaskey has repeatedly shown up in unscripted moments that resonate with fans. He chased linebacker TJ Edwards through the tunnel as he was carted away with a season-ending injury. After a massive win over Green Bay at Soldier Field, McCaskey quietly paid for the Uber rides of Bears fans trying to get home — a small gesture that instantly became legend among the fans in attendance.
Those moments matter. But so do the bigger decisions.
When it came time to reset the direction of the franchise, McCaskey didn’t hesitate to open the checkbook to land Ben Johnson, making it clear the Bears were done cutting corners at the most important position in the organization. That move alone signaled a philosophical shift fans had been waiting years to see.
The results of that shift came into sharp focus during the Bears’ unforgettable late-season run in 2025.
The Bears-Packers rivalry remains one of the most storied rivalries in all of sports, and last season added two historic chapters. After dropping the first matchup, Chicago stormed back in Week 16 and followed it up with a dramatic Wild Card victory that will live in franchise lore.
In Week 16, the Bears trailed by ten points late before recovering an onside kick following a Cairo Santos field goal. Quarterback Caleb Williams then delivered a clutch touchdown pass to undrafted rookie Jahdae Walker, forcing overtime.
Chicago sealed the comeback on a walk-off touchdown reception by DJ Moore, winning 22–16.
In the Wild Card round, the Bears erased a 21–6 fourth-quarter deficit to stun Green Bay once again, pulling off a 31–27 comeback that sent Soldier Field — and much of Chicago — into chaos.
McCaskey then stood behind his head coach's use of profanity referring to the franchise's rival after that win. Another refreshing change.
Speaking with WGN-TV’s Jarrett Payton, McCaskey admitted those wins affected him just as deeply as they did the fanbase.
He joked that after the playoff victory — which he humorously referred to as beating “Team Voldemort” — he struggled to focus on work, instead watching viral videos of Bears fans celebrating across the city.
“After the playoff win against Team Voldemort, when we’re getting ready to play the Rams, I had trouble getting work done because I was watching all the viral videos,” McCaskey said. “The videos of people just going crazy in their houses, or running into the street and hugging strangers.”
Those are the moments that reveal why the relationship between McCaskey and Bears fans feels different now.
He teared up publicly talking about what the Bears mean to the city of Chicago. He has spoken openly about carrying the emotional weight of the franchise — not just as an owner, but as someone who understands what Sundays feel like for millions of fans across the city.
That vulnerability is fairly new. And it’s endearing.
Fandom alone doesn’t guarantee success. But Bears fans have always wanted to believe that the person at the top feels the same joy, pain, and urgency that they do. Over the past year, McCaskey has shown — through both words and actions — that he does.
With momentum carrying into the 2026 season, the Bears have an owner who isn’t just writing checks or standing on ceremony. They have one who lives and breathes the moments alongside the fanbase.
For a franchise built on tradition, that connection still matters.