Trent Williams
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PHILADELPHIA, PENNSYLVANIA - JANUARY 11: Trent Williams #71 of the San Francisco 49ers celebrates after his team's 23-19 win against the Philadelphia Eagles in the NFC Wild Card Playoff game at Lincoln Financial Field on January 11, 2026 in Philadelphia, Pennsylvania. (Photo by Elsa/Getty Images)
Just when the Chicago Bears figured out a core starting five up front on offense, rookie left tackle Ozzy Trapilo suffered a patellar tendon injury.
According to general manager Ryan Poles, he expects Trapilo “to be back and be himself,” but the team is still expecting him to miss the majority of next season.
“We expect him to come back and heal from it,” Poles said. “There’s a plan in place. I can’t get into the timeline or anything like that, I just don’t know. But, yeah, we expect him to be back and be himself. Pretty significant injury that he’s got to get through, but in terms of affecting his overall career or next year, I don’t see that being an issue.”
Now, the Bears are tasked with finding a stopgap replacement at left tackle. Although the team is bringing back Theo Benedet on a one-year deal, having Joe Thuney switch to left tackle during the playoff loss to the Los Angeles Rams should say everything you need to know about how the Bears feel regarding their situation at LT.
The Bears’ starting left tackle likely isn’t on the roster right now for the 2026 season; however, a dream opportunity could open up, according to ESPN’s Adam Schefter.
Future Hall of Fame left tackle Trent Williams and the San Francisco 49ers are “struggling to find a contractual solution,” and if the two sides can’t come to an agreement, Williams could join this year’s free-agent class, instantly making him the top free agent.
That said, Harrison Graham of Chat Sports made a compelling case for how the Bears could sign Williams.
Bears Receive Compelling Trent Williams Take
Despite needs on defense, it’s hard to pass up an opportunity to bring in a future Hall of Famer and create the best offensive line in the NFL. And according to Graham, the Bears can do this in a two-year, $50 million deal with $30 million guaranteed.
“How much would it cost the Bears or another team to bring him in? I think guaranteed money would be the key. To me, I’d be looking at this like a one or two-year deal. Probably a two-year deal to manipulate the cap a little bit and you probably have to give him about 28 or even 30 plus million dollars guaranteed. 2 years, $50 million with 30 guaranteed, whereas there’s kind of an out after this upcoming year with a dead cap penalty of less than $10 million if both sides want to move on. It’s pretty tempting. And I know you’re saying, ‘Well, Harrison, defense, defense, defense,’ and I hear you. But he instantly becomes the best free agent available if he gets cut.”
It would be a lot of money for a guy who’ll be 38 by the time next season rolls around, but he’s still a top-three left tackle in the NFL who ranks third in overall PFF grade (91.5), 12th in pass block grade (79.9), and 2nd in run block grade (92.8).
The Reality: It’s a Long Shot
The reality is the 49ers love having Williams on the team, and the Bears would have to be magicians to find a way to lure him to Chicago as the team currently is over the cap with negative $4.1 million available, according to OvertheCap.com.
“Look, Trent Williams, I’m sure, would prefer to stay with San Francisco,” Graham added. “The Niners prefer to keep him. They have big offensive line issues if they don’t. And it is a long shot, but if it happens where he frees up and becomes available, as a free agent, to be clear, I’m not trading for that contract. I don’t think anyone is. But if he became available, I’m interested. I mean if I’m Ryan Poles, I’m at least checking in with Trent Williams’ agent like, ‘Hey, what are you looking for in the guarantees,’ and you know, if we can make something work, maybe this is a situation where it’d be worth adding a void year to keep that cap hit because you would still want to spend some money on the defensive side of the ball.”
If Williams ends up staying with the 49ers, then it was fun to imagine a world where he lines up next to Thuney on the left side of the offensive line. However, if he does in fact get released, then it shouldn’t be ruled out that Poles won’t try to see if there’s a way to bring him to Chicago for one or two years.