Bears are taking a massive risk with their approach to uneven left tackle position

The Chicago Bears had four players start at left tackle throughout the 2025 NFL season.

Braxton Jones, Theo Benedet, Ozzy Trapilo, and Joe Thuney all lined up as the primary protectors for Caleb Williams’ blindside. It was the one position on the offensive line last season that experienced inconsistency, and that fluctuation at left tackle could be in line to happen again.

With Trapilo’s torn patellar tendon that he sustained in the Wild Card victory over the Green Bay Packers, the Bears have made a series of moves to add competition at left tackle. The Bears have reportedly re-signed Braxton Jones to a one-year deal worth up to $10 million. Interestingly, Jones wasn’t included in a recent news release by the team that announced Chicago’s five other re-signings.

According to ESPN’s Adam Schefter, the Bears have also agreed to a one-year deal with Jedrick Wills Jr., a former No. 10 overall pick in the 2020 NFL Draft. The 6-foot-4, 307-pound offensive tackle has only played in 58 games since 2020, and he didn’t play a single game during the 2025 season.

Examining the Bears' left tackle position in 2026

The Bears still have 2024 third-round draft pick Kiran Amegadjie and undrafted free agent Benedet on the roster as well. General manager Ryan Poles has assembled a group of players who will have something to prove as they compete for one of the most important positions on the football field.

One of these left tackles has to separate themselves at some point during the left tackle competition. Ideally, that would allow the offensive line unit, which will have a new starting center in Garrett Bradbury, to establish consistency as the season progresses.

If the competition drags out, which is definitely a possibility, then that limits the time on task for all the players. However, what will help is that whoever wins the job will line up next to a future Hall of Fame player in Thuney.

The Bears could also draft a left tackle high in the upcoming draft, which would signal a more long-term solution, but Williams and the offense would have to endure the growing pains of a rookie lineman.

How the left tackle position becomes solidified will be a storyline throughout the entire summer, but the Bears can’t afford to have someone become a consistent liability at the position, especially since the organization will be striving to build off a successful first season under head coach Ben Johnson.