The 2025 season was supposed to be the Chicago Bears' return to relevance. Competitive football and a possible Wild Card spot were really the ceiling of expectations. But under the creative wizardry of Ben Johnson, Chicago didn't just compete; they took the NFC North crown and secured a top-two seed.
But for general manager Ryan Poles, the euphoria of a division title was quickly replaced by the cold reality of a medical report.
When Ozzy Trapilo clutched his knee during the Wild Card victory over Green Bay, the trajectory of the Bears' 2026 offseason shifted instantly. And now, with Trapilo facing a grueling recovery from a torn patellar tendon that will keep him sidelined "deep into next year," the Bears are staring at the most dangerous question in football: Who is going to protect Caleb Williams’ blindside?
The Theo Benedet Experiment
The Bears acted fast this week, re-signing Theo Benedet to a one-year deal. While Benedet showed flashes as a run blocker last season, his pass pro metrics remain a major red flag. Allowing 26 pressures on just 313 snaps is a recipe for disaster, no matter how creative or athletic your signal-caller is when pressure is in his face.
Relying on Benedet as the primary solution isn't just a risk; it's a gamble with the franchise's crown jewel.
The Safety Vacuum and the Cap Crunch
The offensive line isn't the only fire Poles have to extinguish before the draft. The Bears are currently looking at a secondary that is, quite literally, empty. With Kevin Byard III, Jaquan Brisker, and C.J. Gardner-Johnson all expected to hit the open market, Chicago currently has zero safeties under contract.
Byard, the NFL’s 2025 interception leader, has expressed a desire to return, but the price tag won't be cheap. Compounding the issue is a tightening salary cap.
With DJ Moore ($28.5 million) and Montez Sweat ($25 million) eating up massive chunks of the pie, the Bears may be forced to choose between veteran leadership in the secondary or a blue-chip protector for Williams.
When the NFL Draft kicks off in Pittsburgh, the Bears will sit at No. 25 overall with options likely to be available up front. In a draft class deep on defensive talent but top-heavy at tackle, Poles has a difficult choice. Does he spend that pick on a high-upside protector like Georgia's Monroe Freeling, Arizona State's Max Iheanachor, or Alabama's Kadyn Proctor to secure Williams' future, or does he plug the defensive holes and pray that a patchwork offensive line can hold up?
Read more: Senior Bowl Spotlight: Derrick Moore and Day 2 edge option for Bears
The answer to the question could determine if 2025 was a one-year wonder or the beginning of something special in the Windy City.