Four Words That Blue States Cannot Say
Ron DeSantis said this to me in January: “How can we help?”
This past January, I met with Florida Governor Ron DeSantis about a major capital project that I’ve been working on. My team has Miami, Orlando, Atlanta, Nashville, and Dallas-Fort Worth on our list. I walked him through the details of the proposal. He asked sharp questions, demonstrating that he was (unsurprisingly) both well-briefed and thoroughly engaged.
When I finished, the governor asked one question: “How can we help you bring this to Florida?”
I almost burst out laughing. It wasn’t that what Governor DeSantis asked was funny. It’s that I’ve spent a lifetime in Illinois, and it’s impossible to imagine any elected official back home asking a business executive how the government could help. Whether in Chicago or Springfield, the question Illinois leaders ask is always the exact opposite: What can you do for us?
When you want to build something in the Land of Lincoln, you know you’ll need to pay extra to get permission. Perhaps it’s a special concession, a promise to hire only certain unions, or put in a community benefits agreement that puts cash in the pockets of some favored constituency. This practice has a name: pay to play. That’s a cute term for very real corruption. In 2025, an Illinois court convicted former House Speaker Michael Madigan for running this exact scheme with a utility called ComEd. (Madigan extracted $1.3 million in payments from ComEd, spreading them among his friends. In return, the utility got favorable legislation from Springfield.) As far as state and local officials in Illinois are concerned, business exists to help them, not the other way around. The idea of a governor asking how he could help, no strings attached? Inconceivable.
The Missed Shot Heard Around the Field
Last week, as you’ve probably heard, the Chicago Bears announced they were moving to Indiana. Well, not quite: the team’s board of directors declared that they’d voted to advance a stadium development project in Hammond, thirty miles southeast of the Windy City. The move came after the Illinois General Assembly failed yet again to pass any financing bill for the team. While I am not a fan of taxpayer funding of private assets, Illinois is the state that pioneered the model for public-private capital projects (including the current Soldier Field, McCormick Place, Navy Pier, and Millennium Park) cannot seem to find a way to keep an iconic NFL franchise that has called Chicago home for more than a century.
Generations of Chicagoans have grown up loving the team they affectionately call “Da Bears.” Through good times (eight NFL championships before the Super Bowl era, plus the 1985 Lombardi Trophy) and bad times (a 3-13 record in 2016), fans have stayed loyal. New York has two NFL teams, as does L.A. Chicago has only the Bears. So even if the team’s name stays the same, and even if some fans will make the regular trip down I-94 to the new stadium in Indiana, the impending departure is a profound cultural loss.
That unnecessary loss has less to do with money than with a fundamentally perverse view of private enterprise that infects both state and local government.
No one – not even the most self-serving politician – denied that the Bears needed a new stadium. Soldier Field is more than thirty years older than any other facility in the league, and further retrofits and enhancements would be inadequate. Yet when the team approached state and local officials for help, they encountered the same logic I’ve watched destroy company after company, job after job during my years fighting in Illinois politics. The state didn’t ask: How do we make this work?
Instead, every layer of government asked a version of the same question: What can we extract?
Notes From the Inside
All of this was frustratingly familiar. In my time leading Illinois Policy, we battled AFSCME, the Chicago Teachers Union, and the SEIU: all public-sector unions that regarded state and local government as a piggy bank from which to extract maximum compensation. We spent years fighting against an entire system that treated businesses as either nuisances or prey. We won some battles but lost too many others.
I watched Ken Griffin -- who had spent more than thirty years doing business in Chicago and who had built Citadel into a multi-billion-dollar company -- conclude that he could no longer stay in the state he’d grown to love. I’ve watched a dozen other businesses reach the same calculation. It wasn’t because they couldn’t handle a Chicago winter. It was because they had grown exhausted with fighting off state and local governments hellbent on extraction. In Illinois, if you create value, it’s the government’s job to figure out just how much of that value they can squeeze out.
The City That Tested the Theory
This contempt for business and wealth creation is not limited to Illinois. We see it in almost every “blue” state and city. Think of Oakland, which not so long ago was the home of not one, not two, but three championship-winning professional teams. Since 2019, this Northern California community of 440,000 people has lost the NFL’s Raiders, the NBA’s Warriors, and the MLB’s Athletics to other cities. To paraphrase Oscar Wilde, to lose one franchise might be misfortune, to lose two might be carelessness, but to lose three? That’s a colossal failure of public policy and common sense that can only happen where the left is in charge.
Each departure meant the loss of jobs, tax revenue, economic vitality and civic pride. Each departure could have been avoided if far-left city officials had focused on wealth creation rather than extraction.
Business Goes Where It’s Treated Well
The Chicago Bears are moving to Indiana because the Hoosier State knows what Illinois leaders refuse to accept: when you make it easy for private enterprise to succeed, everyone benefits. Capital can always pick up and move – just ask Ken Griffin or the Las Vegas Raiders. Successful businesses go where they’re welcome, and they go where elected officials ask not what they can get, but what they can do to help.
Indiana has only about half of Illinois’ population, but it may soon have two professional football teams while Illinois will have none. Indiana will enjoy that advantage because their elected officials know that prosperity is a function of attraction rather than extraction. Indiana’s leaders – like Ron DeSantis in Florida -- asked, over and over again, how they could help, and so “Da Bears” are headed where they are welcome and wanted. Countless other entrepreneurs, small business owners, and major corporations alike will continue to do the same.
I’d like to think the imminent loss of such a beloved cultural institution will cause the far-left politicians in Illinois to rethink. Recent history, alas, suggests they won’t.
I recall a business owner who moved his business from Chicago to Austin. He was amazed at the warm ‘how can we help’ greeting in Austin compared to the bureaucratic hostility in Chicago. Somebody else said ´nothing changes without pain.’ I wonder when we will reach the tipping point.
All of what you say is probably true of Illinois. But your article is ostensibly about the McCaskey family building a new stadium and choosing the Hammond site because the Illinois legislature wouldn’t help fund the site the McCaskey’s own in Arlington Hts. It seems that in this situation, it is not the state doing the extracting but the McCaskeys. Study after study has shown that public financing of sports stadiums is a losing proposition for taxpayers. Perhaps the more appropriate question here is why the Indiana legislature is willing to use its taxpayers money to fund a stadium that will primarily be used by residents of Illinois. As a renowned advocate of entrepreneurship, I would expect you would be applauding Illinois, chastising Indiana and urging the McCaskeys to arrange private financing for their stadium.