Will Chicago Revisit Familiar Territory at Left Tackle in 2026?

NFL

The 2025 season was a year that Bears fans will remember for a long time. All season long, the team had miraculous wins and outstanding performances. However, the year ended with a heartbreaking loss to the Los Angeles Rams. While there were many positives to build on, one major hole appeared. Starting left tackle Ozzy Trapilo suffered a ruptured patellar tendon in the previous game against the Green Bay Packers. Chicago must now turn its attention to finding its temporary replacement to solidify the offensive line. Luckily for them, some familiar faces could help with that. 

The first, and potentially top option, is Theo Benedet. The 24-year-old joined the team as a free agent and was a name that few Bears fans knew. After a crowded pre-season competition, he entered the year as the backup left tackle. He first started in Week Four due to injuries at right tackle. Following that game, he switched back to left tackle and took over as the starter. This resulted in him starting a total of eight games. Throughout the year, he struggled in pass protection but excelled in the run game. In November, a quad injury led to Trapilo becoming the starter. Benedet was unable to regain his starting job; however, he clearly made an impact in Chicago and was rewarded with a one-year, one-million-dollar contract. 

This low price tag does allow the Bears to explore other options. One name they have been connected to is Braxton Jones. The former fifth-round pick has been a long-time contributor for Chicago. In four years, he started a total of 44 games. This past season, he actually was the starting left tackle before getting benched in Week Four. Following this, he dealt with a knee injury and spent the rest of the regular season on injured reserve. The 26-year-old may not be an elite option, but he could be an affordable one. He is a free agent, but coming off an injury and little playing time, his price tag should not be too expensive. 

These two surely are among the top candidates to hold down the starting spot until Trapilo is ready. However, there are also questions about how much the Bears trust them. Against the Rams, Chicago decided to shift Joe Thuney, an elite left guard, to left tackle. This move shocked many, as both of these other players were options. Benedet had been fully healthy and was consistently appearing in games as a sixth offensive lineman. Additionally, Jones had been activated from the injured reserve the week leading up to the game and appeared to be healthy.

Ultimately, the left tackle situation will be one of the critical decisions that the Bears need to address to continue their success. Familiar options would build on the chemistry from last season and offer short-term stability. However, the team's playoff decision suggests that there may not be enough trust in those solutions. The idea of adding another option through the draft or free agency is available, but Chicago also needs to direct their focus towards the defense. In the end, bringing back one of these familiar options may be the most practical path to ensuring stability while continuing to improve the rest of the roster. 

Tyler Courtney

Tyler Courtney is a Sport Management Major at the University of Minnesota-Twin Cities . He has all the passion for sports and would like to help connect others to it, with the hopes it can help them in the ways that sports have helped him.

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