The guy is holding blueprints in the middle of a horse track. It’s a windy Saturday in January 2026, and George McCaskey is standing in the middle of the old Arlington Park property with NFL Commissioner Roger Goodell. This isn't just a site visit. It’s a statement.
For years, the narrative around the Chicago Bears and George McCaskey was one of stagnation. Fans chanted "sell the team" until they were hoarse. They looked at the McCaskey family as the "mom and pop" shop trying to compete in a world of tech billionaires and private equity. But things are different now.
George McCaskey is no longer just the chairman; he is the owner. Since the passing of the legendary Virginia Halas McCaskey in early 2025 at the age of 102, the "playbook," as George calls it, has been passed down.
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Honestly, nobody expected the 2025 season to go the way it did. A division title? A playoff win over the Packers? Ben Johnson has turned Halas Hall into a "frenetic" energy zone, and suddenly, George McCaskey looks like a man who finally pushed the right buttons. But behind the wins on the field, a massive financial and structural shift is happening that most fans haven't fully grasped yet.
The Tax Man Cometh: The $160 Million Problem
You’ve probably heard the rumors. The McCaskeys are "cash poor." While the Bears are valued at nearly $8.8 billion, the family doesn't have a side hustle like a hedge fund or a global oil empire. Their wealth is the Chicago Bears.
When Virginia passed, a massive tax bill came with the inheritance. We’re talking upwards of $160 million. You can’t exactly put that on a credit card.
This is why the ownership structure of the Chicago Bears is quietly undergoing its biggest shakeup in a century. George has been firm: the family isn't selling. "Another 100 years would be great," he said recently. But "not selling" doesn't mean "not changing."
To cover those taxes and fund a multi-billion dollar stadium project, the McCaskeys are finally looking outside the family tree. Pat Ryan, the insurance mogul who already owns a chunk of the team, has been spending a ton of time at Halas Hall. The plan? Bring in more minority investors. Maybe even dip into the newly allowed NFL private equity pool.
It’s a balancing act. George wants to keep the Halas legacy intact while acknowledging that the old way of doing business—where one family handles everything—just doesn't work in 2026.
The Stadium Chess Match: Arlington Heights vs. Indiana?
If you saw the photos of George McCaskey, Kevin Warren, and Roger Goodell touring Arlington Heights last week, you saw a man under pressure.
The Bears are in a weird spot. They own the land in Arlington Heights, but the property tax disputes with the local school districts have turned into a nightmare. Meanwhile, Chicago's leadership has been lukewarm on the team's previous domed-stadium proposals near the lakefront.
Then came the curveball.
Suddenly, Northwest Indiana is in the conversation. The team actually sent out surveys to season-ticket holders asking how they’d feel about a dome in Hammond or Gary.
Is it a leverage play? Probably. George McCaskey isn't a typical cutthroat negotiator, but Kevin Warren is. By bringing Goodell to see both the Arlington site and the Indiana options, the Bears are sending a clear message to Illinois Governor JB Pritzker: we have options.
Pritzker has called some of the team's financing requests "non-starters," but the tone has shifted lately. There’s talk of including stadium infrastructure in the "Rebuild Illinois" capital plan. George is essentially holding the blueprints and waiting for someone to make the math work.
George McCaskey and the "Football People"
For a long time, George’s biggest flaw—according to the 190 North faithful—was his tendency to get too involved or hire the wrong consultants. Remember the Ernie Accorsi days?
But the current version of George McCaskey seems to have finally learned the art of the "hands-off" approach. He let Ryan Poles build the roster. He let Kevin Warren handle the politics. And most importantly, he backed the hiring of Ben Johnson, who has brought a level of offensive creativity this city hasn't seen since... well, maybe ever.
McCaskey’s relationship with Johnson is interesting. He describes the coach as "intense" and "demanding." During the 2025 season, when Johnson went on a viral, expletive-filled rant about the Packers, George didn't fine him. He didn't issue a corporate apology. He reached out and told Johnson he loved the passion.
That’s a big shift for a chairman who used to be seen as overly concerned with the "Bears Way" of being polite and traditional.
What Most People Get Wrong
- The "Cheap" Narrative: People think the McCaskeys won't spend. The reality is they spend to the cap every year. The "cheap" issue isn't the roster; it's the lack of "liquid" cash for massive infrastructure without taking on partners.
- The Sale Rumors: Every time a new billionaire is mentioned, people think George is ready to cash out. He’s not. He views himself as a steward of his grandfather’s (George Halas) legacy.
- The Decision Maker: Kevin Warren runs the business. Ryan Poles runs the draft. George is the guy who asks, "How does this help the fans?" and "Does this honor our history?"
Why the Next Two Years are Critical
The Chicago Bears are at a crossroads that will define the next fifty years of the franchise. By the end of 2026, we will likely know exactly where the new stadium will be. We will also see a new list of minority owners on the team’s masthead.
George McCaskey is trying to navigate a transition that has sunk other family-owned franchises. He’s dealing with a massive inheritance tax, a stadium battle, and the pressure of a fan base that finally has a taste of winning.
He’s still the guy who sometimes works the ticket office. He’s still the guy who drives a modest car and talks about his mother with tears in his eyes. But he’s also the guy who just oversaw the most successful Bears season in a generation.
The "mom and pop" shop is becoming a corporate titan, whether George likes the jargon or not.
Actionable Insights for Fans and Investors
If you're following the McCaskey era, keep your eyes on these three specific indicators over the next six months:
- The May Board Meeting: Watch for announcements regarding "private equity investment." If the Bears approve a 10% sale to a PE firm, the stadium deal is officially a "go."
- Springfield Legislation: If the Illinois legislature doesn't pass a property tax "certainty" bill for Arlington Heights by June, the Indiana threat becomes very real.
- The Ben Johnson Contract: Successful coaches in this era want more than just a salary; they want a say in organizational structure. How George manages the power balance between Warren, Poles, and Johnson will dictate if this "honeymoon period" lasts.
George McCaskey isn't going anywhere. He’s just finally realized that to keep the team in the family, he has to let a few outsiders into the building. It’s a gamble, but for the first time in a long time, Bears fans might actually like the odds.
Next Steps for Following the Bears Ownership Shift:
- Monitor the Cook County Board of Review rulings on the Arlington Park property tax assessments; this is the primary hurdle for the suburban stadium.
- Track the NFL’s upcoming votes on private equity ownership limits, as this will dictate how much of the team George can "sell" without losing family control.
- Follow the "Rebuild Illinois" capital plan updates to see if state-funded infrastructure (roads, sewers, transit) is allocated for the Arlington Heights site.