For the second season in a row, the Chicago Bears have a left tackle problem, and for the second year in a row, it’s because of injury.
Last year, head coach Ben Johnson had to scheme around the position as four different players all took reps there.
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In 2026, the Bears need to address the position in free agency rather than move a current offensive line starter to left tackle. Four of Chicago’s starting o-linemen are playing at a high level, so I want to see that continuity continue to thrive while integrating just one new starter into the mix.
Here are the Bears’ current offensive tackles.
Darnell Wright – Signed through 2026* – The 24-year-old Wright missed out on his first Pro Bowl, but was named a second-team All-Pro at right tackle, and right tackle is where I hope he stays.
Just like last offseason, the speculation has already started about Wright moving to left tackle, but I don’t buy it. Considering the talented pass rushers who normally rush off the defensive left edge, Wright is too valuable where he’s at.
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The only way I see him flipping sides is if the Bears can’t find a stopgap at left tackle this offseason and they sign a free agent they feel could step in on the right side and be serviceable.
Regardless of his position, he’s in line for a massive contract extension, which will put his annual salary north of $20 million per year.
*The fifth-year option is available for the Bears in 2027.
Braxton Jones – Free agent – The injury Jones suffered two years ago robbed him of a showcase season in the final year of his contract. Had Jones been fully healthy, he likely would have held on to the Bears’ starting left tackle spot while they developed Trapilo, which would have allowed Jones to essentially audition for a deal elsewhere in 2026.
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Jones’ rehab slowed his progress, and he then began favoring his injury in games, so the Bears had to bench him. Another injury landed him on injured reserve, which he was activated from before the season’s end, so he’s presumably healthy now.
Theo Benedet – Signed through 2026 – Kudos to Benedet for starting eight games at tackle following his practice squad rookie year. He was a solid run blocker, but his limitations in pass protection were evident. He may be able to improve his technique enough to start at left tackle in 2026, but I don’t think the Bears will count on that.
His play style looks more like a guard to me, so if the Bears can bolster tackle this offseason, maybe we see a different role for Benedet in 2026.
Ozzy Trapilo – Signed through 2028 – Trapilo was thrust into the mix to start at left tackle in the offseason, but he didn’t capitalize, and didn’t look very good in preseason. But credit to him and the coaching staff, because when he was called on later in the year, he looked like the future at the position.
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However, the knee injury he suffered in the playoffs has his 2026 season in doubt.
The Bears should be cautious with their 2026 second-round draft pick, and if that means missing all of ‘26, then so be it.
Kiran Amegadjie – Signed through 2027 – Most thought Amegadjie needed a redshirt year after being drafted out of Yale in 2024, so let’s just consider 2025 as that redshirt. He was inactive for the first couple of games in 2025 before landing on IR with an elbow injury, but prior to that, he was in the mix for the left tackle spot during camp. I think that was more due to no one stepping up than it was his performance, but heading into year three, we’ll learn pretty quickly where the Bears see his ceiling.
2026 OUTLOOK – If Braxton Jones is healthy, which is still a big if, he seems like the best option to be back on a one-year deal to play left tackle. Before his injury, he was playing solid football, and yes, his anchor was an issue, but after the 2024 season, Pro Football Focus had him as a top-20 tackle. The injury did more than just rob him of a showcase year; it robbed him of a chance to work on that anchor all offseason. He’s no doubt been working as hard as possible since the season ended, and no one will know where he’s at better than the Bears.
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If Jones isn’t an option, then a few other possibilities are Minnesota’s Justin Skule, New England’s Vederian Lowe, and Seattle’s Josh Jones, who all have starts at left tackle last season and at least 25 o-line starts in their career.
This NFL Draft feels like it’ll be defense on the first couple of days, but a day three offensive tackle like Clemson’s Tristan Leigh would be a developmental guy that o-line coach Dan Roushar could work with.
What do you think the Bears will do at offensive tackle this offseason, and in particular, what do you think their plan is for left tackle?
