The Chicago Bears made several key moves that allowed the franchise to turn itself from a 5-12 squad that finished last in the NFC North in 2024 to an 11-6 division champion one year later, but the biggest leap forward came on the offensive line.
Part of that unit's ascension involved the development of second-round rookie Ozzy Trapilo into an above-average starting left tackle. However, the Bears lost Trapilo during their opening-round playoff victory over the Green Bay Packers in January by way of a ruptured patellar tendon and aren't likely to get him back before late in the 2026 regular season -- if at all.
The best option available in free agency to replace Trapilo is 10-year veteran Taylor Decker, who has spent his entire NFL career to this point with the Detroit Lions. Decker started 140 games for the Bears' rival, including 46 contests across three years (2022-24) under Ben Johnson who served as Detroit's offensive coordinator over that span before becoming the head coach in Chicago in 2025.
Bears taking huge risk by not spending on left tackle this offseason
It would make sense for the Bears to invest significantly in Trapilo's replacement given the importance of the left tackle in any offense, but particularly to one in Chicago where quarterback Caleb Williams is entering a pivotal third NFL season. However, Johnson and general manager Ryan Poles have declined to do so.
The team brought back Braxton Jones on a one-year deal after he lost his job early last year amid multiple injury concerns. The Bears also inked Jedrick Wills Jr., a former first-round bust of the Cleveland Browns who didn't play a single snap in 2025, to a league minimum contract. Theo Benedet, who played snaps at LT last season before Trapilo took over the job permanently, is also on the roster heading into training camp.
Decker earned a Pro-Bowl nod in 2024 and will play the upcoming campaign at 33 years old. Spotrac projects his market value at upwards of $43 million over a new two-year contract, which might be a longer-term deal and more money annually than Chicago wants to pay with a younger and less expensive solution in Trapilo slated to come back (hopefully) in time for the end of 2026.
That said, Decker's relationship with Johnson is something the Bears should at least try to leverage in an effort to get the offensive lineman in the door for training camp. Even if Chicago has to pay Decker for two years, he's worth the money in 2027 given everything the team has at stake right now.
The Bears aren't just defending a division title, their first since 2018, or trying to get back to the playoffs after doing so last season for the first time since 2020. Chicago is attempting to build a multiyear momentum for the future behind the Johnson-Williams tandem, and that duo is at a crossroads in 2026 -- particularly with regards to the young QB's development.
Williams has yet to miss a game in his career, starting all 34 regular season contests and both playoff outings since Chicago drafted him No. 1 overall in April 2024. Now is not the time for the team to scrimp on the blindside of a player who has the ceiling of an NFL MVP and the best quarterback in the league if everything shakes out right over the next couple seasons.
Worst-case scenario, Decker is an overpaid a swing tackle in Chicago behind Trapilo and second-team All-Pro selection Darnell Wright (RT) in 2027.
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