Former Bears Guard's Prediction Would Lead to Huge Upset in Crucial Position Battle

With a major question mark at left tackle, the Chicago Bears have given themselves multiple options at the position.

That question mark comes from the uncertain status of Ozzy Trapilo, who may not play at all this season after suffering a ruptured patellar tendon during last season's playoffs.

With Trapilo on the shelf, the Bears are going to have a competition at the position throughout the offseason.

That competition will include Braxton Jones, who was benched in 2025, former Cleveland Browns first-round pick Jedrick Wills and Theo Benedet.

Former Bears guard makes bold prediction

Cleveland Browns offensive tackle Jedrick Wills Jr. against the Philadelphia Eagles at Lincoln Financial Field. — Former Cleveland Browns offensive tackle Jedrick Wills Jr. | Eric Hartline-Imagn Images

During a guest appearance on "Kap and Hood" on ESPN 1000, ex-Bears guard and analyst Tom Thayer boldly predicted that Wills would end up being "the steal of the offseason."

"The steal of the offseason is gonna be Jedrick Wills," Thayer said. "If he can come out here and he's healthy, and he can compete from Day 1, he's gonna give you an opportunity to (have) what once was a big-time football player."

There are a few reasons why that prediction is bold.

For starters, staying healthy has been the biggest problem Wills has had during his career, as he has dealt with recurring injury issues.

Wills then sat out the entire 2025 season to rehab his knee and correct what he called an "alignment issue."

“I injured a couple of ligaments, but usually when people like when they get fell on or something in their knee, they mess up all their ligaments and people can just go in and repair it and they get healthy," Wills said, via Zack Pearson. "I had minimal damage to my ligaments. It was more of an alignment issue from where I got fell on. So they had to actually – it wasn't my knee, they had to go into my femur and do what was called an osteotomy to kind of correct my alignment. So my knee is healthy.”

When he was on the field in 2024, Wills' play was bad enough that he got benched.

His overal body of work hasn't been great, either. He has certainly not lived up to the billing of a top-10 pick.

Perhaps the procedure done on his knee will change things and elevate Willis to a new level in 2026, but as of right now, Jones remains a safe bet to win the competition at left tackle.