Bears President Fumbled Key Stadium Deal That Changed Everything

A botched stadium bid, political hurdles, and a legacy in ruins-how Ted Phillips set the Bears relocation plans off course from the very beginning.

The Chicago Bears’ long, winding journey toward a new stadium might finally be approaching its end - but not before a few more twists in a saga that’s been years in the making.

Let’s rewind to 2021. Back then, longtime team president Ted Phillips approached the Chicago Park District with a proposal to upgrade Soldier Field.

Among the ideas floated: installing a sportsbook to generate a new revenue stream. But the pitch never got off the ground - literally.

The city didn’t just say no; they didn’t respond at all. Crickets.

That silence turned out to be a turning point. Frustrated and looking for options, Phillips and the McCaskey family made a bold move: they placed a bid on the Arlington International Racecourse property in Arlington Heights. It was the most serious sign in decades that the Bears were ready to leave the lakefront behind and plant roots elsewhere.

Fast forward three years, and while the Bears do now officially own the Arlington property, the dream of a sparkling new stadium remains just that - a dream. The team hasn’t broken ground, and the reasons are layered.

On one hand, the state has been hesitant to commit public dollars toward infrastructure improvements. On the other, a major sticking point has emerged around property taxes.

According to reporting, the tax issue is what’s really bogged everything down. Before finalizing the purchase, the Bears didn’t lock in an agreement on how the property would be taxed - either in its vacant state or after development.

Once the state reassessed the land’s value post-sale, the tax bill ballooned. And the Bears weren’t exactly eager to pay that higher rate.

It’s a costly oversight, and one that’s left current team president Kevin Warren in cleanup mode. The situation underscores just how complex stadium deals can be - especially when public funding, tax law, and private ownership all collide.

Now, in fairness, hindsight is always 20/20. But it’s hard not to look at the timeline and wonder how things might have gone differently if the Bears had approached the purchase with a more buttoned-up plan.

Stadium development isn’t just about land and blueprints - it’s about navigating the political, financial, and legal frameworks that come with it. And in this case, that navigation was off course from the start.

Still, there’s reason for optimism now. Talks between Warren and state leaders have picked up momentum in recent weeks.

Governor J.B. Pritzker has already signed legislation that could make it easier for the Bears to secure infrastructure funding.

The final piece of the puzzle? A proposed megaprojects bill that would allow the team to negotiate a more manageable property tax rate.

If that passes, the path to construction becomes a whole lot clearer.

And if all goes according to plan, the Bears will stay in Illinois - just not in Chicago. Arlington Heights remains the destination, and the vision of a state-of-the-art stadium anchoring a new entertainment district could finally start to take shape.

It’s been a long road, filled with missteps and missed opportunities. But now, for the first time in a while, the Bears’ stadium future feels like it’s within reach.