Who should start for the Chicago Bears at left tackle going forward?

Ozzy Trapilo played well against the Steelers. Did he do enough to earn the right to start at left tackle moving forward?

Jun 3, 2025; Lake Forest, IL, USA; Chicago Bears offensive tackle Ozzy Trapilo (75) warms up during minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

I personally didn't expect Ozzy Trapilo to play well against the Steelers on Sunday. Not after how quickly they gave up on the prospect of him moving to the left side (they didn't get through training camp before throwing in the towel on that project).

I've never been happier to be wrong. Trapilo played lights out against Pittsburgh's stout defensive front.

Ozzy Trapilo had a damn impressive starting debut at left tackle. pic.twitter.com/D3zZ7efc9S

— Harrison Graham (@HGrahamNFL) November 24, 2025

The matchup was far from easy, too. Nick Herbig is no slouch. He had 6.5 sacks entering the game and is one of the league's most underrated pass-rushers. Trapilo completely neutralized him.

Ben Johnson didn't feel the need to protect the rookie, either. He was left on an island 13 times against Pittsburgh and allowed only one pressure (and no sacks or QB hits). Even with Darnell Wright having a difficult matchup against T.J. Watt on the other side, that's a huge vote of confidence in the rookie.

The important question now is, did he do enough to supplant Theo Benedet, who missed the game with a quad injury? I personally think he did.

For starters, while Benedet has been a road grader in the running game, he's been a liability in pass protection. He's a major reason why Caleb Williams earned a reputation as a Houdini-level escape artist. When a defender gets to Williams quickly, and the defense isn't sending extra rushers, it's often because Benedet missed his assignment.

Would they miss what the Canadian Eagle brought to the running game? Maybe, but that would only be the case if Trapilo is a liability in that department. With that said, it's much easier to scheme around an offensive tackle who isn't as dominant in the running game than one who isn't as good in pass protection.

Another reason why it makes sense for Chicago to move forward with Trapilo at left tackle is the investment they made in him. Darnell Wright isn't going anywhere anytime soon. He's having a Pro Bowl caliber season and looks like one of the league's best right tackles. What does that mean for the guy they drafted in the second round? It ultimately means he would be relegated to swing tackle duty if he doesn't have a future on the left side. That's not a role you want from the guy you felt confident enough to select 56th overall.

Hear from Ozzy Trapilo after his first start at LT: pic.twitter.com/D16Tz8L86M

— CHGO Bears (@CHGO_Bears) November 23, 2025

They drafted Trapilo to play on the left side. They initially thought he could be the answer there. Would it make sense to move away from that after only one start in which he looked like the answer there? I don't think so.

Former Bears center Olin Kreutz knows a thing or two about offensive line play. He, too, came away very impressed with how well Trapilo played against Pittsburgh.

"Very efficient, he played a very good game," Kreutz said on 670 The Score's Mully and Haugh show. "He really put himself in position not to get beat."

I honestly give Benedet credit for holding down the left tackle job as long as he did. The offensive line has performed much better with him in the lineup than it did with Braxton Jones, who was in line for a hefty payday this offseason if things had gone differently for him this season. He will enjoy a long career in the NFL as a reserve lineman (at the very least).

Benedet's a quality swing tackle who the team could start in a pinch. Not too shabby for a player the team picked up off the scrap heap following the 2024 NFL Draft. However, I don't believe he's the answer to the team's left tackle equation. Trapilo, on the other hand, might be.

I think they should definitely give the Boston College product an extended look at left tackle to close out the season. That would help them decide whether they need to prioritize adding the final piece to the offensive line in the offseason. It would be a MASSIVE win for Ryan Poles and company if they don't.

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