The Bears exceeded expectations in 2025, capturing the NFC North title for the first time since 2018. They pulled off a dramatic second-half, 18-point comeback to beat the Packers in the Divisional Round rematch before pushing the Los Angeles Rams to overtime, ultimately falling 20-17.
Defensive progress under veteran coordinator Dennis Allen helped Chicago’s ascent, while quarterback Caleb Williams took noticeable steps forward in his sophomore season under offensive-minded head coach and play-caller Ben Johnson. Still, the left tackle position remained an area of concern despite overall offensive line improvements.
Trapilo’s injury highlights the urgency: the current left tackle will miss substantial time in 2026, and questions linger about whether he can return to his prior level. With the injury, Chicago could look to add a trusted, proven starter to stabilize the blind side as Williams and Johnson continue to develop.
Walker enters free agency as the top left tackle option on the market, having started over Morgan in Green Bay and delivering a solid 64.6 PFF grade last season. He also faced off-field scrutiny after a recent arrest at LaGuardia airport on gun-related charges, a factor that could influence market demand and price.
Spotrac projects Walker at roughly $20 million per year, a figure that could deter some teams. If the Bears could land Walker for closer to $14-16 million annually, with only a modest dead-cap penalty after two seasons, the deal could represent a strong value for a left tackle need that directly impacts Williams’ development and Chicago’s long-term outlook.
Ultimately, signing Rasheed Walker would align with a strategic, risk-balanced approach for the Bears: bolster the left tackle spot with a known commodity, leverage Ben Johnson’s familiarity with Walker, and manage cost in a way that preserves remaining cap flexibility. As March free agency approaches, Chicago’s front office will weigh on-field value against off-field considerations in this hypothetical scenario.
