If there is one thing we have learned about Caleb Williams’ family since he joined the Chicago Bears, it’s that they are enterprising. They treat business every bit as seriously as football. Williams already has an extensive investment portfolio, and he has said he hopes to keep it growing as his career progresses. Undoubtedly, he learned this mentality from his father, Carl Williams. The family patriarch is a prominent businessman who owns a performance training facility in Washington, D.C., and is a respected real estate developer.
One thing we’ve learned about the man is he’s not afraid to stick his nose into things that the fathers of athletes usually don’t. He tried to find a way out of the Bears drafting Caleb two years ago, even consulting with lawyers on the NFL’s collective bargaining agreement. Now it appears he is aiming for something a little more in his wheelhouse but no less ambitious. According to Justin Lawrence of Crain’s Chicago Business, Williams has become involved with a team of developers aiming to pitch the Bears on a site for their new stadium in downtown Chicago.
Caleb Williams may be trying to tie himself to the franchise even more.
“There are zero proposals in Chicago right now that have the Bears, you know, actively working on them. But there are four sites where developers and/or City Hall are gearing up to make another go at the Bears. They’ve all been batted about before, some publicly, some not so publicly. But those are, like we said, in Bridgeport (Guaranteed Rate Field), where if the Chicago White Sox move either to the 78 or to this new Railyards proposal that Justin Ishbia is pushing, you know, that opens up that area. It’s owned by the state through the Illinois Sports Authority already. So some have this idea, including Sterling Bay, and like we said, Caleb Williams’ father, Carl Williams, is now involved in that, to bring the Bears there on the lakefront just to replace Soldier Field.”
Pinning down when this began hasn’t become clear. All this is known is that Williams aligned himself with Sterling Bay, a developer that has done tons of work in downtown Chicago, including McDonald’s Global HQ.
“It’s still a little unclear how he got involved. You know, he is a developer himself. He’s involved in a kind of like a sports performance, like almost like a youth training facility somewhere. But he has shown up with Andy Glore CEO of Sterling Bay. You know, they’ve built up Fulton Market. They had the failed proposal of Lincoln Yards. Prominent developers in Chicago that have had some setbacks recently, but they’re still around. And Sterling Bay is working with Justin Ishbia on his plan. Somewhere along the way, Caleb Williams’ father, Carl Williams, got involved.”
Some speculate that Sterling Bay is hoping to use Caleb Williams’ popularity, through his father, to get a meeting with the Bears. A bit sneaky, perhaps, but certainly effective.
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Caleb Williams may no longer have an angle.
Part of the advantage that his father and Sterling Bay had was that Bears president Kevin Warren was the one primarily interested in hearing proposals for a downtown stadium. It is pretty obvious that this has been his endgame for years, since he pivoted the team away from Arlington Heights to pursue the museum campus three years ago. That obviously didn’t go anywhere for several reasons, but Warren’s ongoing relationship with Chicago mayor Brandon Johnson suggested he hadn’t given up on the idea. If anybody would’ve been intrigued by Bridgeport, it would be him.
The problem is he isn’t the one calling the shots anymore. Recently, the Bears made changes to their negotiating team with Springfield last month. Part-owner Pat Ryan became the one to speak with government power brokers with assistance from NFL commissioner Roger Goodell. Warren appears sidelined. If that is the case, then Carl Williams may have lost their best chance to pitch the Bears on Bridgeport. Most believe Ryan and Goodell are focused on getting a deal done for Arlington Heights.
This situation is certainly complicated.
It was no secret that several competing parties have made pitches to the Bears about putting a stadium in different locations. Probably the most consequential have been various groups from Chicago who are working hard to prevent an Arlington deal from going through. They want to keep the team in the city and have been scrambling for solutions. The two most notable were the Michael Reese Hospital site, which the Bears don’t like due to infrastructure issues. The other is the South Works, where U.S. Steel used to be. Neither gained much traction.
Bridgeport feels like it might be a solid compromise. It’s just 5 minutes south of Soldier Field and has already been a neighborhood built around a sports franchise for years. The Bears could build a state-of-the-art stadium on the site of the demolished Guaranteed Rate Field and then revitalize the neighborhood with amenities to attract fans. Since it remains downtown, the revenue possibilities would be more extensive. No doubt that is a big reason Caleb Williams and his father might be interested in being part of it.
Presuming the necessary legislation passes this month, they will have a chance to pitch the Bears. It better be a strong one, because Arlington Heights feels like the heavy favorite at this point.
