Written by GP
Cheap at Any Price: George McCaskey Will Borrow $2 Billion Before He Sells You a Single Share
There is a version of the Bears stadium saga where the McCaskeys are simply broke — a faded football dynasty, asset-rich and cash-poor, priced out of the modern NFL by billionaires who treat franchises like superyachts. It’s a tidy story. It’s also wrong, and believing it lets George McCaskey off the hook for the actual decision he just made.
The family is not broke. At the league’s official $8.9 billion valuation, the McCaskeys’ roughly 77.5% stake is worth north of six billion dollars on paper. What they are is illiquid — and, more to the point, unwilling to do anything about it. Because the alternative to illiquidity is selling a piece of the team, and selling a piece of the team is the one thing this family will not do, even when every spreadsheet in America is begging them to.
So instead, they’re going to borrow.
The money was always right there
The NFL has spent the last few years loosening the very levers that exist for exactly this situation. Teams can now sell up to 10% to institutional investors and private-equity funds. At an $8.9 billion valuation, that single lever is worth roughly $890 million — nearly half a stadium — raised without a bank, without a bond, without owing anyone a payment.
That’s the small option. There’s no hard cap on selling to an existing partner, so long as the family keeps the 30% the league requires it to hold for control. The McCaskeys sit at 77.5%. That leaves them room to sell roughly 23 percentage points — about two billion dollars at today’s valuation — to Pat Ryan, or to anyone else with a checkbook, and still walk away with a clear majority of the team.
Two billion dollars. The exact cost of the stadium. Available without a dime of debt. Sitting in plain sight. And they will not touch it.
This was never about the money. It was about the grip.
Pat Ryan is the obvious buyer, which is precisely why he’s the unthinkable one. The Aon founder is an insurance billionaire whose personal fortune dwarfs the entire McCaskey clan’s liquid wealth several times over — the man wrote a nine-figure check to put his name on Northwestern’s new football stadium more or less for sport. He already owns 22.5% of the Bears. Selling him another slice would solve the cash problem in an afternoon.
It would also tilt the franchise’s center of gravity toward the guy with the deeper pockets — and that is the line the McCaskeys will not cross. Virginia McCaskey’s death in February 2025 scattered her stake and her votes across roughly eleven children, some of whom, by multiple accounts, would happily take liquidity. The family’s response to that fragility has not been to professionalize or to raise outside capital. It’s been to clutch tighter. George’s stated ambition, relayed from his brother Pat, is to own this team “until the second coming.” That’s not a business plan. That’s an heirloom being white-knuckled past the point of competence.
So the math gets inverted. A rational owner sells a non-controlling slice, funds the building, and keeps the team home.
The McCaskeys would rather load a century-old franchise with two billion in debt and exile it across a state line than let one more percentage point slip toward someone who might actually outvote them someday.
That’s the real definition of cheap. Not “won’t spend money.” Won’t part with control at any price — even when the price of keeping it is the soul of the franchise. They would rather build in a swamp and cross a state line. May I remind George that old man Halas got his start at the University of Illinois on Illinois money. What a prick.
Every other family in this town figured it out
This is the part that should sting. The Ricketts financed Wrigley’s reinvention and built a neighborhood around it. The Reinsdorf and Wirtz families got the United Center redevelopment moving on private capital. Justin Ishbia is building a White Sox stadium that doubles as transit infrastructure for the CTA. Joe Mansueto is paying for an entire Fire stadium himself. Himself!
Four Chicago ownership groups. Four ways to self-fund and stay. Every one of them found the nerve to put their own money — or someone else’s equity — into keeping their team where its fans are. Those are owners that should be celebrated while the McCaskey family should be spit on for their petty greed.
The fucking Bears, who looked at the exact same toolkit, decided that selling Pat Ryan a sliver of a team he already partly owns was a fate worse than debt, and started shopping for moving trucks to Indiana. WTG.
What this is really about
The choice in front of George McCaskey was never Illinois versus Indiana. The geography is the symptom. The choice was control versus competence — between a family that would rather rule a diminished, indebted, relocated franchise outright than co-own a thriving one that stayed home. They appear publicly with Ryan, but they despise him. They fear him.
George picked control. He always picks control. And the bill for that vanity — two billion dollars of it — is going to come due on a franchise that George Halas built and his heirs are slowly, stubbornly, immovably running into the ground. Lori Lightfoot was a corrupt asswipe who looked like Betelgeuse, but she had one threat right: go get the Arizona Cardinals and put them in Soldier Field and leave the Bears to Indiana. The NFL would never allow it, but wow would it be the best fuck you to the Bears ever. The return of the Chicago Cardinals.
The McCaskeys can afford the fucking Arlington stadium. What they cannot afford is letting go. And until that changes, no amount of Ben Johnson magic or Caleb Williams brilliance is going to save Bears fans from the one opponent the front office can’t scheme around: its own greedy, vain owners.








