I Love Chicago. That's Why This Bothers Me.

I’m not a casual fan. As a family, we’ve been to a lot of Bears games. Cold ones. Ugly ones. Hopeful ones where you talk yourself into believing this year is different.

And for a moment this past season, it actually was.

I’ve lived here long enough to know the reflex. Whenever the Bears come up, the conversation goes sideways fast.

Money. Loyalty. Greedy owners. Billionaires shaking down taxpayers. The lakefront is sacred. Soldier Field is history.

Some of that is true. None of it explains what’s actually happening.

The Bears aren’t threatening to leave Chicago. They’re responding to it. And when they go, it won’t be because the city stopped caring. It will be because Chicago cared deeply about the wrong things and refused to decide.

This isn’t a new failure mode. It’s a very old one.

Because watching something you love finally come together makes the stakes of losing it feel very real.

This Past Season Made It Personal

2025 was different.

Caleb Williams didn’t just change the Bears. He changed the feeling. The confidence. The way the city leaned forward instead of bracing for disappointment.

Comebacks that felt impossible. Poise that didn’t make sense for someone that young. And then the thing Chicago fans had waited a lifetime for: beating the Packers in the playoffs.

Soldier Field finally felt alive again. Not nostalgic. Alive.

The frigid cold seemed to disappear after DJ Moore caught Caleb Williams’ pass with 1:43 left to take the lead over the Packers in the playoffs.

Which is why the timing of all this matters.

We just watched the Super Bowl yesterday. The season closed. And almost immediately the conversation snapped back to reality: Arlington Heights. Northwest Indiana. Leases. Timelines.

And the familiar pit in the stomach.

Chicago Has Been Here Before. Literally.

In the early 1900s, Chicago was originally awarded the 1904 Olympics. Most people don’t know that. They assume St. Louis won a bid. It didn’t. Chicago lost the games.

Not because the city lacked ambition. Not because it lacked money. But because it couldn’t agree on whether building a permanent stadium in a public park violated its values.

The opposition didn’t vote the stadium down. They didn’t defeat it publicly. They delayed it. Challenged it. Moralized it. Slow-walked it until the timeline collapsed.

The International Olympic Committee didn’t punish Chicago. It just chose certainty. St. Louis already had a facility tied to the World’s Fair. Messy, but guaranteed.

Chicago kept its principles. It lost the games.

That pattern never left.

The Burnham Paradox We Never Resolved

Daniel Burnham gave Chicago its soul. Vision. Aspiration. The idea that a city should be beautiful, intentional, and worthy of pride.

“The lakefront belongs to the people” is one of the most powerful civic ideas in American history.

It’s also operationally incomplete.

Burnham designed what the city should look like. He didn’t design how it should decide when values collide with reality.

Chicago institutionalized the vision without building an execution model around it. Over time, ideals hardened into vetoes. Preservation became a way to avoid accountability. Nobody had the authority to say yes, only the standing to say no.

That works fine until the world changes.

Soldier Field Wasn’t a Mistake. It Was a Symptom.

The 2003 renovation didn’t fail because of incompetence. It failed because it tried to reconcile irreconcilable goals.

Keep the monument. Protect the lakefront. Modernize the stadium. Don’t upset taxpayers. Don’t anger preservationists. Don’t give the team too much control.

The result was predictable. The smallest stadium in the NFL. Bad fan experience. Capped revenue. No long-term optionality.

Chicago preserved the symbol and froze the system.

That’s not compromise. That’s paralysis dressed up as virtue.

And Now We’re Surprised the Bears Are Looking Elsewhere?

This is the part we need to be honest about.

Modern professional sports isn’t about football games. It’s about year-round economics, development rights, certainty, and speed.

You don’t get that through task forces and public posturing. You get it by giving someone clear authority and holding them accountable for outcomes.

Chicago doesn’t do that well. Not because it’s corrupt or dumb. But because it treats large infrastructure decisions as moral debates instead of system design problems.

The suburbs aren’t selling out. They’re offering clarity.

And clarity creates gravity.

This Isn’t About the Bears. It’s About Leadership.

And this is where my day job leaks into my fandom.

I see this exact pattern inside companies all the time.

Teams that talk endlessly about values but never define decision rights. Organizations that confuse consensus with alignment. Leaders who protect symbols instead of building systems.

Values that aren’t encoded into decision-making don’t protect institutions.

They paralyze them.

This is something I think about constantly.

You can’t will alignment into existence. You have to design for it. Gravity beats persuasion. Systems decide long before people do.

When no one is empowered to decide, the system decides by default. And default outcomes favor speed, certainty, and whoever is willing to move.

That’s not betrayal. That’s physics.

Loving Something Means Wanting It to Work

This isn’t anti-Chicago. It’s the opposite.

I love this city. I love its ambition, its stubbornness, its belief that things should mean something.

But meaning without execution doesn’t scale.

Leadership isn’t about defending the past. It’s about designing structures that let values survive contact with reality.

Chicago keeps winning the argument and losing the outcome.

The Bears leaving won’t be the tragedy.

The tragedy will be pretending this came out of nowhere.

Because whether it’s a football team, a company, or a city, the pattern is the same.

When you don’t design systems that can decide, the outcomes will decide for you.

And they usually don’t stay loyal.