Bear Digest

Bears Could Fill Massive Need in Free Agency With Future Hall of Famer

Adding a five-time All-Pro left tackle should be a no-brainer for the Chicago Bears.
Pete Martuneac|
Eric Hartline-Imagn Images

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Chicago Bears

Lost amid the euphoric celebrations following the Chicago Bears' miraculous Wild Card win over the Green Bay Packers was the devastating injury update on standout rookie left tackle Ozzy Trapilo. After hobbling to the sideline on Chicago's final offensive drive of the game, it was reported that Trapilo's injury was even worse than we thought: a ruptured patellar tendon. From that moment on, it became clear that Trapilo would likely not be cleared for football for a long time, and general manager Ryan Poles confirmed at the NFL Combine on Tuesday that Trapilo will miss the majority of 2026.

What does this mean for the Bears? Once again, left tackle is a massive need as they enter the offseason. Braxton Jones is due to hit free agency, and the Bears are unlikely to bring him back. Theo Benedet started a few games at left tackle this year, but the undrafted rookie was mostly a liability on the Bears' offensive line.

After exceeding expectations in 2025, the Bears can ill afford a step back in 2026, least of all from Caleb Williams. Their future depends on Williams' breakout season being a trend, not a one-off. To prevent him from regressing, they need to ensure that his offensive line remains one of the best in football, and that means that general manager Ryan Poles must find a good left tackle who can start immediately and be relied upon for at least one season.

It sounds like an impossible task, but the perfect solution may in fact be about to hit free agency. Five-time All-Pro left tackle Trent Williams is in the middle of a contract dispute with the San Francisco 49ers, according to ESPN's Adam Schefter, and if neither side can come to an agreement, the future Hall of Famer could be looking for a new home next month.

Trent Williams could be Jason Peters 2.0

Stop me if you've heard this one before: while the Bears await their long-term solution at left tackle, they should spend big money on a 39-year-old veteran who is a lock for the Pro Football Hall of Fame. They did exactly this in 2021, when Ryan Pace signed Jason Peters to a one-year deal to protect rookie Justin Fields' blindside.

The move was a smashing success, despite another losing season for the Bears. Peters earned a 77.5 grade from Pro Football Focus, which at the time was the best grade given to a Bears tackle since 2017. The nine-time Pro Bowler proved that age truly is just a number when you're the best of the best, and that's exactly what Trent Williams is.

A short-term deal between Williams and the Bears is a match made in Heaven

He may be 39 years old, but Williams is still one of the best left tackles in football, and guys like that don't hit the open market very often. If he does become available, the timing couldn't be more perfect for the Bears, given Trapilo's injury. The Bears need at least one year, and perhaps two, of good left tackle play until either Trapilo returns or they draft another left tackle, and Williams is as close to a sure thing as anyone will find in free agency. Signing him to a short-term deal with a hefty bonus to minimize his cap hit should be a no-brainer for Ryan Poles.

As aforementioned, the Bears can't allow all the success and hope from 2025 be for naught. They have to ensure that Caleb Williams will continue to be the best-protected quarterback in the NFL so that he can become the superstar they know he can be.

Trent William
Eric Hartline-Imagn Images

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Pete Martuneac
PETE MARTUNEAC

A former Marine and Purdue Boilermaker, Pete has been covering the Chicago Bears since 2022 as a senior contributor on BearsTalk. He lives with his wife, two kids and loyal dog.

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