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Bears head coach Ben Johnson.
The Chicago Bears will have some difficult decisions to make about their roster in the 2026 NFL offseason after breaking their 15-year playoff win drought, but one of those decisions could come relatively easily to Ryan Poles’ front office.
Over the next five weeks, the Bears must figure out how to create more 2026 cap space through a combination of veteran roster cuts, contract restructures and — in some cases — contract extensions before the start of the new league year at 4 p.m. ET on March 11.
Chicago is also likely to re-sign at least one of its pending free agents, such as Pro Bowl safety Kevin Byard III, to ensure key talent remains in place before free agency starts.
Several weeks later, the Bears will have another decision to make about the future of second-team All-Pro right tackle Darnell Wright before the May 1 deadline to pick up his fifth-year option for the 2027 season — with a projected value of $20.5 million.
As The Chicago Tribune’s Brad Biggs sees the situation, though, the Bears are “likely” to pick up Wright’s option, at which point he would expect them to start working toward signing their former first-round pick to a “multiyear” contract extension past 2027.
“The Bears likely will exercise the fifth-year option in his contract and then would be expected to sign him to a multiyear extension,” Biggs wrote on January 30. “Wright’s third season was easily his best despite playing most of the year with a torn ulnar collateral ligament in his right elbow, missing only the Week 4 game in Las Vegas.”
Darnell Wright Could Undergo Surgery Before 2026
Wright has largely developed how the Bears envisioned he would when they passed on defensive tackle Jalen Carter and traded back to the 10th overall pick to select him.
In 2025, Wright was the driving run-blocking force for the Bears’ third-ranked rushing offense (144.5 yards per game), earning Pro Football Focus’ seventh-best run-blocking grade (85.6) among all offensive tackles. He also gave up three sacks and 19 pressures in pass protection, an improvement from 2024 despite a too-high penalty count (11).
Wright’s elbow, however, could give the Bears pause when discussing an extension.
As Biggs mentioned, Wright played most of the 2025 season with a torn ulnar collateral ligament in his right elbow, missing only one game because of the injury. He also said that it remains “uncertain” if Wright will undergo surgery on his elbow in the offseason.
If Wright does have surgery, the Bears may reasonably decide to wait to start any long-term extension talks until he is healthy again and back on the practice field. Then again, Wright’s toughness playing through the injury in 2025 may shine through and tell the Bears’ front office that they have seen enough to keep him around well beyond 2027.
How Will Bears Handle Left Tackle Position in 2026?
The Bears will likely have a straightforward decision to make with Wright’s fifth-year option in about three months, but what they will do at left tackle is much less clear.
Second-round rookie Ozzy Trapilo seemed to finish the season as the Bears’ top choice at left tackle after starting in their final six regular-season games and their playoff win over the Green Bay Packers, but his status for the start of the 2026 season is uncertain after he ruptured the patellar tendon in his knee in the victory over the Packers.
Even if the Bears are optimistic that Trapilo could be ready for the start of next season, they will likely need to find a capable backup plan at the position, whether they sign a veteran in free agency to help bridge the gap or target a new left tackle in the draft.
The options in free agency are relatively light, but the Bears could consider re-signing Braxton Jones, who missed most of 2025 with an injury after an early-year benching. While Jones has clearly fallen out of favor, the Bears may feel that his experience is too valuable to let him walk out the door, if they can re-sign him to an affordable contract.
Otherwise, the Bears’ best choices could come in the 2026 draft. It is not unreasonable to think the Bears might target a left tackle with their No. 25 overall pick in the first round, especially if they feel good about the defensive line depth for the later rounds.
Jordan J. Wilson is a sports reporter who covers the NFL and MLB for Heavy.com, with a focus on the Chicago Bears and Green Bay Packers. He has previously covered all levels of sports — high school, college and pro — for a variety of publications including The Indianapolis Star, The News-Gazette, Springfield State-Journal Register and Peoria Journal Star. More about Jordan J. Wilson
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