Bears’ Moves May Spell Trouble for Caleb Williams in Year 3

The Chicago Bears face growing unease about their left tackle position entering 2026, after a dynamic 2025 offseason that briefly vaulted the team from worst to first in the NFC North but left the line vulnerable to a steep drop-off. The combination of re-signing Braxton Jones, adding Jedrick Wills Jr., and the abrupt end to Ozzy Trapilo’s rookie-year starter arc has created a fragile balance that could undermine Caleb Williams’ development if protection fails.

In retrospect, several 2025 moves exceeded expectations and earned a measure of grace for head coach Ben Johnson and general manager Ryan Poles. Center Drew Dalman delivered a Pro Bowl-caliber season after a lucrative free-agent signing, Colston Loveland emerged as a cornerstone of the passing game, and Trapilo showed promise at left tackle before an early playoff injury. These outcomes tempered initial criticism and underscored the plan’s potential.

However, the offensive line remains Chicago’s most uncertain unit heading into the next draft cycle. Williams’ third season hinges on a stable frontline, and the group’s up-and-down pass protection in the previous year highlighted the risk of regression if depth and consistency erode. The Bears’ ability to integrate Williams’ skill set with a sturdier pass shield will be a defining storyline as free agency settles and the draft approaches.

Jones’ return on a modest deal and Wills’ addition carry implications beyond immediate performance. Jones struggled with injuries and consistency as the frontline shifted, while Wills’ health and performance after a lengthy absence will determine whether he can anchor the left side or if further reinforcements are required. The evolvingLeft tackle scenario casts a long shadow over the team’s long-term offensive strategy.

Analysts have noted that Johnson’s run-game design and the offensive-line overhaul helped elevate Williams from a challenging rookie year to a more competent operator in recent seasons. Yet the current depth chart and the uncertain health timeline for Trapilo leave Chicago with a high-stakes question: can the Bears sustain their improved line play and minimize sacks and pressure in 2026?

With the NFL draft still ahead, there remains an opportunity for Chicago to shore up the left tackle spot or add versatile linemen who can bridge the gap until Trapilo returns from injury. The team’s success in this offseason hinges on protecting Williams, enabling a more diverse passing attack, and maintaining the momentum generated by last year’s upward trajectory. The next few months will determine whether the Bears can convert potential into sustained performance behind a more reliable frontline.