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Bears’ Biggest Free Agency Winners, Losers Revealed by Insider

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LAKE FOREST, ILLINOIS - JULY 22: General manager Ryan Poles of the Chicago Bears speaks to the media ahead of the start of Chicago Bears Training Camp at Halas Hall on July 22, 2025 in Lake Forest, Illinois. (Photo by Michael Reaves/Getty Images)

The first wave of NFL free agency is officially in the books. The Chicago Bears have quietly reshaped many parts of their roster and are looking ahead to taking another step forward in 2026.

While general manager Ryan Poles has not landed the blockbuster addition many fans were hoping for yet, Chicago still managed to add several key pieces while maintaining financial flexibility. The moves have left analysts across the league debating which players and figures within the organization benefited the most and who may have taken a step back.

According to Bears analyst Anthony Miller, Poles deserves significant credit for how the team approached the opening week.

“Despite spending limits, the Bears’ general manager, Ryan Poles, managed to create some cap space while keeping key players and adding new talent,” Miller wrote.

Chicago’s strategy focused less on splashy signings and more on strengthening depth across multiple positions. Additions like safety Coby Bryant and linebacker Devin Bush, along with the signing of offensive tackle Jedrick Wills Jr., gave the roster several experienced contributors heading into the next phase of the offseason.

Ryan Poles, Coby Bryant Among Early Bears Winners

The biggest winner from the Bears’ opening week may be Poles himself.

Poles especially deserves credit after center Drew Dalman’s unexpected retirement threw a wrinkle into the Bears’ offseason plans. He quickly addressed the position by adding Garrett Bradbury from the Patriots and bringing in Jedrick Wills to reinforce the offensive line.

Although Chicago was linked to major names like Maxx Crosby and Trey Hendrickson earlier in the offseason, Poles instead prioritized building depth while keeping long-term flexibility intact.

“Coby Bryant and Devin Bush are upgrades at their positions, and Jedrick Wills Jr. might end up being the steal of free agency,” Miller wrote.

Bryant, in particular, landed one of the most significant deals of the Bears’ free-agent class. The safety agreed to a three-year contract worth $40 million, making him the team’s highest-paid addition so far.

Bryant will have a massive opportunity to be a key piece of the Bears’ defense going forward.

Meanwhile, offensive tackle Braxton Jones also emerged as an unexpected beneficiary of the free-agent market. Jones returned to Chicago on a one-year deal reportedly worth $10 million, positioning him to compete for a starting role again in 2026.

Bears Defensive Changes Create Uncertainty

While several names emerged as winners, the Bears’ defensive changes have created uncertainty elsewhere on the roster.

Linebacker T.J. Edwards was highlighted as one of the early losers following Chicago’s decision to add Bush and re-sign depth linebacker D’Marco Jackson. The moves could potentially reduce Edwards’ long-term security within the defense.

The Bears’ secondary as a whole may also face the biggest challenge moving forward.

Chicago lost several defensive backs in a short period, including Kevin Byard, Jaquan Brisker, Nahshon Wright, C.J. Gardner-Johnson and Jonathan Owens. With so much turnover at the position, defensive coordinator Dennis Allen now faces the task of rebuilding a completely reshaped unit before the season begins.

With free agency still unfolding and the NFL Draft approaching, Poles still has time to further improve the roster.

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