With Ozzy Trapilo sidelined deep into the 2026 season, the Bears opted for familiarity at left tackle, bringing back Braxton Jones on a one-year deal worth up to $10 million to protect Caleb Williams’ blindside.
With Ozzy Trapilo suffering a ruptured patella during the Chicago Bears’ playoff win over the Green Bay Packers, the injury left Chicago in a difficult position heading into the offseason.
The Bears didn’t just lose their starting left tackle for the remainder of the playoffs—forcing them to kick Joe Thuney outside in the divisional round against the Los Angeles Rams. They also lost their presumed left tackle of the future to an injury that is expected to sideline him well into the 2026 season.
And with Chicago aiming to return to the postseason, that created a significant—and potentially expensive—hole to fill along the offensive line.
Complicating matters further, the Bears weren’t exactly entering the offseason with cap space to burn.
At the same time, the team clearly does not trust Theo Benedet to step in as the starting left tackle in 2026, making the free-agent market the most logical avenue for a solution.
On Monday night, however, the Bears finalized a different plan. Rather than look externally, Chicago decided to go internal at the position, bringing back Braxton Jones on a one-year deal worth “up to $10 million.”
The deal is worth $5 million with an additional $5 million in incentives.
Jones entered the 2025 season as the Bears’ starting left tackle but was coming off ankle surgery following a fractured fibula that ended his 2024 campaign. He never quite appeared fully healthy. Jones started the first four games of the season but struggled significantly, surrendering 15 pressures and two sacks before ultimately being benched.
He did not take another offensive snap after Week 4, and after losing the starting job, he suffered a knee injury in Week 7 that ended his season entirely.
Yet here he is again—returning on a one-year contract that could once again place him in charge of protecting Caleb Williams’ blindside.
The reality is likely simple: the Bears ran out of better alternatives they trusted at a reasonable price.
Jones has 44 career starts under his belt and already has familiarity with Ben Johnson’s offensive system and protection schemes. It’s also possible the organization believes his struggles in 2025 were at least partially injury-related. In that sense, this deal functions as a classic prove-it contract, with a $5 million bridge agreement representing the cleanest short-term solution for both sides.
It may not be the most exciting move on the board, and the reaction from Bears fans is unlikely to be overwhelmingly positive. But finding a reliable left tackle in free agency is notoriously difficult. Quality options rarely reach the open market.
And despite inconsistent play at left tackle throughout the 2025 season, Chicago’s offense still managed to function at a respectable level.
These are the kinds of compromises teams must make when navigating salary-cap constraints while trying to build a more balanced roster. So far, the Bears’ primary focus in free agency has been improving the defense.
If the organization (and fanbase) believes in Ben Johnson’s vision, it also has to trust his plan for the offensive line—and his ability to scheme around some of the imperfections currently present up front.