The Chicago Bears dramatically improved their offensive line in 2025, helping fuel one of the NFL’s most effective rushing attacks. However, the unit has taken multiple blows this offseason, leaving the team searching for stability at a critical position — left tackle.

After a season of progress under head coach Ben Johnson, Chicago now faces a challenging situation protecting franchise quarterback Caleb Williams heading into the 2026 season.

Injuries and Retirement Create Major Hole on Bears’ Offensive Line

The Bears’ offensive line troubles began during the playoffs when rookie left tackle Ozzy Trapilo suffered a torn patellar tendon in the first round. The injury is expected to sideline him for most of the upcoming season, leaving Chicago without a clear long-term answer on Williams’ blindside.

Shortly afterward, the team was dealt another major blow when Pro Bowl center Drew Dalman unexpectedly retired just one year into a three-year contract while still in the prime of his career.

The combination of Trapilo’s injury and Dalman’s retirement has forced Chicago to reassess its offensive line plans despite the strong performance of the unit last season.

Run-Heavy Offense Increases Importance of Left Tackle Position

Under Johnson, the Bears shifted toward a powerful rushing attack that became one of the league’s best in 2025. While the strategy helped accelerate the development of Williams, protecting the young quarterback remains a top priority.

Without Trapilo available for much of the 2026 campaign, Chicago must find a left tackle capable of supporting the run-first system while also protecting Williams’ blindside.

The team was unable to find the right value for that position during the 2026 NFL Draft, which has led analysts to suggest the Bears may turn to free agency.

Former Lions Star Taylor Decker Emerges as Potential Solution

One player who could fill that gap is veteran tackle Taylor Decker, a longtime starter for the Detroit Lions.

Decker spent a decade anchoring Detroit’s offensive line and earned Pro Bowl honors in 2024. Earlier this offseason, he requested his release just one year into a $60 million contract, and the Lions granted the request.

According to Tyler Sullivan of CBS Sports, Chicago could be the best landing spot for the veteran tackle due to his previous relationship with Johnson.

Sullivan noted that Decker could provide valuable insurance at left tackle for the Bears as they wait for Trapilo to recover.

Competition Already Exists on Chicago’s Roster

Chicago has already taken steps to reinforce the position. The Bears signed Jedrick Wills Jr. earlier in the offseason and re-signed Braxton Jones to a one-year contract.

Jones previously lost the starting job to undrafted rookie Theo Benedet last season before Trapilo eventually secured the role.

However, the current options present uncertainty. Wills struggled earlier in his career and missed all of last season due to injury, while Jones and Benedet have yet to establish themselves as consistent long-term starters.

Bears Face Difficult Decision at Left Tackle

Signing Decker would come with financial considerations. According to projections from Spotrac, the veteran tackle could command a two-year contract worth around $42.65 million.

That investment could limit the value Chicago gets from Trapilo’s rookie deal, which runs through 2028. However, the Bears must balance long-term planning with the need to protect their young quarterback and maintain the momentum they built last season.

At 30-plus years old, Decker’s performance has begun to decline slightly based on advanced metrics. Even so, he remains one of the most experienced and reliable left tackles still available in free agency.

For a Bears team looking to protect Williams and continue its offensive rise, adding the veteran blocker may represent the safest short-term solution.