The Chicago Bears may focus heavily on defense in the upcoming National Football League draft because of several roster weaknesses on that side of the ball. However, one significant concern on offense remains — and it’s a problem the team may be better positioned to solve through free agency.

At left tackle, Chicago doesn’t necessarily require a long-term answer. Their 2025 second-round pick, Ozzy Trapilo, stepped into the role late last season and performed well during the second half of the year. Unfortunately, Trapilo suffered a ruptured patellar tendon during the team’s first-round playoff victory over the Green Bay Packers. The injury could keep him sidelined for a significant portion of the upcoming season.

In the meantime, the Bears re-signed Braxton Jones to a modest one-year deal worth $5 million. Jones had previously lost the starting job to Theo Benedet before Benedet eventually gave way to Trapilo. Chicago also brought in Jedrick Wills Jr., a former first-round selection of the Cleveland Browns, on a one-year contract worth the league minimum of $1.2 million. Wills did not play at all in 2025 while recovering from injury and appeared in just 13 games across the previous two seasons.

The organization remains hopeful that Jones — who dealt with injuries of his own — can provide stability after adding strength during the offseason. Still, the situation at left tackle remains far from secure. Essentially, Chicago has placed a temporary solution over a major issue at one of the most critical positions on the offensive line while waiting for Trapilo’s recovery.

Rebuilding the offensive line played a huge role in the Bears’ impressive turnaround last season. The team captured its first division title since 2018 and earned its first playoff victory since 2010. But the unit now faces new uncertainty following the unexpected retirement of Pro Bowl center Drew Dalman, leaving the offensive front once again in flux.

Head coach Ben Johnson has a connection that could influence Chicago’s next move. Johnson served as offensive coordinator for the Detroit Lions from 2022 through 2024, and during his final season with the team, veteran left tackle Taylor Decker earned his first Pro Bowl selection.

After spending a decade as Detroit’s starting left tackle, Decker recently requested his release along with the remainder of his $60 million contract so he could explore opportunities elsewhere in the league.

Because of Chicago’s uncertainty at the position and Decker’s familiarity with Johnson’s system, the possibility of the two joining forces again makes sense. The complication is that Trapilo could return later in the 2026 season, though it’s unclear whether his comeback would arrive soon enough to significantly impact the year.

According to projections from Spotrac, Decker’s next contract could be worth around $43 million over two seasons as he enters his age-33 year. Even so, Chicago might view that price as worthwhile to secure a veteran at a premium position and address its most pressing offensive weakness.

Earlier this week, Kristopher Knox of Bleacher Report predicted that Decker could ultimately end up signing with the Bears before the offseason concludes.

Knox noted that Decker has started 140 games across his 10-year career and ranked 41st among all tackles in 2025, according to Pro Football Focus. He suggested the veteran would be a strong option at left tackle, even if the Bears ultimately draft a younger player to develop into the long-term solution.

Knox also pointed out that Chicago might still select a tackle in the upcoming draft, although many of the top prospects in this year’s class have more experience playing on the right side of the line. At the same time, the Bears must also address several defensive needs — including help at defensive tackle, edge rusher, and in the secondary — which could take priority when the draft begins.