Re-Assessing the Chicago Bears Left Tackle Situation With Ozzy Trapilo in the Fold

We didn't know it at the time, but Caleb Williams giving Ozzy Trapilo the moniker of "Wolverine" wound up being a premonition that would make Nostradamus blush. The 6'8", 316 lb. offensive tackle is already back on the practice field after rupturing his patellar tendon seven months ago.

It was truly a miraculous recovery for the second-year offensive tackle, as many believed he'd be sidelined for the entire season. After all, the earliest examples we could find of players returning to the field after suffering the injury was nine months. Again, Trapilo returned in SEVEN.

Trapilo is returning just in time, too. Braxton Jones is dealing with a knee injury (albeit a minor one that shouldn't sideline him when the games matter). Meanwhile, Jedrick Wills Jr. looked like a turnstile against Cleveland. Kiran Amegadjie might not have looked as glaringly bad, but his PFF grades were actually markedly worse.

The Bears' current left tackle situation is awfully similar to what it was at this point last season. They had a revolving door featuring three starters (or four if you count Joe Thuney in the divisional round clash against LA), and Trapilo was easily the most impressive one. Should he be considered the front-runner for the starting job once healthy?

Temper expectations about Trapilo, but he's still the top option

Ozzy Tapilo and Cole Kmet celebrate a touchdown — Nov 28, 2025; Philadelphia, Pennsylvania, USA; Chicago Bears tight end Cole Kmet (85) celebrates after scoring a touchdown against the Philadelphia Eagles with offensive tackle Ozzy Trapilo (75) during the fourth quarter of the game at Lincoln Financial Field. Mandatory Credit: Eric Hartline-Imagn Images | IMAGN IMAGES via Reuters Connect

It would be an understatement to say that Trapilo stumbled out of the gates to begin his career. Despite playing primarily on the right side at Boston College, he was the favorite to start at left tackle entering training camp. That favoritism didn't last long, though. The coaching staff knew he wasn't ready, and he was removed from consideration relatively early.

Trapilo received an opportunity to start in the Week 12 matchup against Pittsburgh, and he made the most of it. Benedet, who started the previous eight games, was great in the running game, but struggled mightily in pass protection. Meanwhile, the rookie held his own in both areas. He was far from perfect, but he stabilized the position that was previously the major weak spot of the line.

With that said, Trapilo still only has seven career starts under his belt. He's still learning how to play on the left side, let alone in the NFL. He's got a lot of growing to do before he establishes himself as a high-end starting left tackle. The injury threw a wrench into that development, as well. Time that could've been spent on improving his technique was also spent on physical therapy.

Trapilo might not be 100% at any point this season, and his anchor might suffer as a result. He's going to experience growing pains. At the same time, his competition is also experiencing growing pains, and two of them (Braxton Jones and Jedrick Wills Jr.) have been full-grown for some time now.

Jed Wills getting smoked by a backup edge, whew pic.twitter.com/IrHbIs9Apu
— Jordan Zirm (@JordanZirm) August 15, 2026

To his credit, his rapid recovery is a good omen for his future. This was the most difficult battle he'll experience in his career, and he dominated it. He's clearly got the drive to succeed, and that should allow him to regain the starting job relatively quickly after he's officially back in action.

Wills, Amegadjie, and Benedet are now all fighting for one spot

Theo Benedet and Kiran Amegadjie lining up — Jul 31, 2026; Lake Forest, IL, USA; Chicago Bears offensive tackle Kiran Amegadjie (72), offensive tackle Theo Benedet (79) and offensive lineman Logan Jones (54) warm up during Training Camp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Images | IMAGN IMAGES via Reuters Connect

The biggest factor from Trapilo returning to the lineup (much) earlier than expected is that someone is going to lose their roster spot. Theo Benedet's job was previously considered relatively safe. He was previously considered the top option at swing tackle and also has experience flexing out to the tight end spot in jumbo personnel. His standing just became a lot less secure, though.

Jones doesn't have any experience getting snaps on the right side, but he's better than Benedet when healthy. If Darnell Wright were to go down for an extended period, would they really start Benedet and leave Jones on the bench just because he doesn't have RT experience? It's also fair to question whether they'll want him eating into Sam Roush's playing time via his niche 13-personnel usage.

If Trapilo starts the year on IR (which has to be still considered a real possibility, even with him living up to his nickname), then he would miss at least the first four games. That would allow them to kick the can down the road, but it would only be delaying the inevitable. They're not going to roster five offensive tackles at any point this season.

Unless Amegadjie has shown the ability to kick inside (a hypothetical he said he's open to), then their fourth option at tackle will be axed once Trapilo is ready to make his debut. That means two offensive tackles will be looking for new homes pretty soon if they don't land back on the practice squad.

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