This Decision Will Define the Chicago Bears' Entire 2026 Offseason

One critical roster choice will shape how the Bears approach free agency, the draft, and their push to build around Caleb Williams in 2026.

Kamil Krzaczynski-Imagn Images

The Chicago Bears' 2026 offseason will ultimately be defined by one position, and it isn't the one most of us thought would be the headliner as the 2025 NFL season dwindled down.

General manager Ryan Poles and head coach Ben Johnson may want to focus most of their resources on fixing the pass rush or bolstering the interior of the defensive line, but the end-of-year injury to left tackle Ozzy Trapilo has once again placed Caleb Williams' blindside protector at or near the top of the team's to-do list over the next few months.

Trapilo was supposed to stabilize the position long-term, but his torn patellar tendon suffered during the playoffs changed everything. Poles acknowledged the severity of the injury, noting Trapilo is expected to be sidelined deep into next year. Patellar tendon recoveries are notoriously unpredictable, especially for linemen whose games rely on anchor, balance, and lateral movement.

Counting on Trapilo in 2026 would be based more on hope than logic.

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Chicago Bears offensive tackle Braxton Jones (70) after the game against the Dallas Cowboys. David Banks-Imagn Images | David Banks-Imagn Images

Unfortunately, the Bears don't have an obvious in-house fix. Braxton Jones enters free agency with 44 career starts. He has experience, and Chicago's decision-makers are familiar with him. If he's re-signed, it'll likely be as a short-term fallback option if Trapilo can't go. His return wouldn't suggest the problem is solved. Sure, he's fine. But Jones returning as the starting left tackle would just be kicking the can down the road.

Theo Benedet made eight starts in 2025 and showed developmental upside. He's worth keeping and developing, but asking him to be the unquestioned starter at left tackle for a contending team is a massive leap. He's more of an asset than a solution.

That's why this decision will define the 2026 Chicago Bears offseason. They must decide how aggressively to pursue a left tackle, depending on how big a problem they view the position right now.

Starting left tackles will be scarce in 2026 free agency. They'll also be really expensive. But protecting Williams' blind side is the most important objective to get right once and for all.

Is Green Bay's Rasheed Walker and his expected $20 million per year price tag the route to go? Will Poles identify a veteran like Cam Robinson (Browns) and his more cap-friendly projected market value of $13 million per year?

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The 2026 NFL draft should present an opportunity to snag a starting-caliber left tackle at No. 25 overall. Drafting a left tackle in the first round would represent more of a long-term answer if the board falls right, but the good ones rarely fall that far. If Poles targets a starter at No. 25, he'd likely end up with a boom-or-bust player.

Offensive tackle prospects who are currently ranked as mid-to-late first-round-picks include Alabama's Kadyn Proctor, Utah's Caleb Lomu, and Georgia's Monroe Freeling.

If the Chicago Bears get this decision right, whether it's investing whatever salary-cap space the team has left or very real NFL draft capital, the offense, under Johnson's watch, will be settled once and for all.

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