The Chicago Bears had to figure out how to attack the left tackle position for the 2026 season after Ozzy Trapillo suffered a significant knee injury in the playoffs in January, and the Bears’ budget appeared to be pretty tight entering the offseason.

When the Detroit Lions released Taylor Decker, given Ben Johnson’s familiarity with his game, everybody circled the Bears as an obvious landing spot. But Decker still hasn’t signed, and the Bears didn’t seem to make a strong push towards Decker, so there was clearly a reason why they didn’t.

Perhaps the Bears felt that Trapillo was going to be ready earlier in the season than many have predicted, and they didn’t want to push Trapillo to the bench for the rest of the season. Perhaps Decker wanted too much money per season for the Bears to fit him in the budget. Perhaps Decker wanted more than a one-year commitment from a team, and that was certainly not something the Bears would consider while Trapillo recovers.

Or, perhaps, the Bears just weren’t interested.

Either way, the Bears chose to sign Braxton Jones to a one-year deal and bring in Jedrick Willis for some additional competition at left tackle.

Wills is an interesting case.

Wills was the 10th overall pick in 2020 by the Cleveland Browns. He was a full-time starter for three years in Cleveland, only missing 5 games over those three seasons. The Browns were pleased with Wllis performance over his first three seasons and picked up the 5th year option.

But things fell apart for Willis in 2023 and 2024. He played a total of 13 games and had multiple significant injuries. Due to these injuries, he decided to sit out the 2025 season.

Willis is back and looking for an opportunity to get back into the fold, and Chicago’s need at left tackle is a perfect spot for him.

Why did Willis sit out in 2025? He basically needed realignment surgery for his hip.

Wills is a low-risk, high-reward opportunity for the Bears. If he returns to form, he can be the Bears’ starting left tackle this year until Trapillo is ready (if he is ready) this year. If he’s decent, he can be the team’s backup tackle behind Braxton Jones, and if he struggles after missing so much time and struggling with injuries, the Bears can move on from him and go another direction.

This isn’t a massive contract for the Bears, but it’s a smart one.