The first wave of 2026 NFL free agency has brought meaningful change to the Chicago Bears roster.

General manager Ryan Poles focused on strengthening the defense with additions such as Devin Bush, Coby Bryant, Neville Gallimore, and return specialist Kalif Raymond.

But free agency is about more than new signings. Every move reshapes the roster, creating opportunities for some players while increasing pressure on others.

After the first two days of free agency, several clear winners and losers have emerged at Halas Hall.

Winner: Bears DC Dennis Allen

Defensive coordinator Dennis Allen may be the biggest beneficiary of Chicago’s early offseason moves.

The Bears’ most significant transactions have focused on strengthening the defense. Adding Bush, Bryant, and Gallimore gives Allen more versatility across all three levels of the defense.

Bush adds speed at linebacker. Bryant provides flexibility in the secondary. Gallimore strengthens the defensive line rotation.

Chicago is entering Year 2 in Allen's defense, and it feels like he got the kind of personnel upgrade that he needed to have much better on-field results in 2026.

Winner: Austin Booker

Third-year pass rusher Austin Booker quietly finds himself in a great position after the first wave of free agency.

Many expected Chicago to pursue a high-profile edge rusher. Instead, the Bears focused on reinforcing other areas of the defense.

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That decision leaves a clear opportunity for Booker to carve out a larger role in 2026. If he takes a step forward in his development, he could become the primary pass rusher alongside Montez Sweat.

Booker ended the 2025 season with 4.5 sacks in 10 games.

Winner: Braxton Jones

When the Bears brought back Braxton Jones on a one-year deal, many assumed Chicago would still pursue a major upgrade at left tackle.

That hasn’t happened; at least not yet.

As things stand today, Jones appears likely to enter the season as the starting left tackle again. For a player entering a prove-it year, that opportunity could be massive.

If Jones delivers a strong season protecting the blind side of Caleb Williams, he could position himself for a much larger contract next offseason.

Winner: Luther Burden

The Bears’ receiving corps also saw a shift earlier this offseason after the team traded DJ Moore to the Buffalo Bills.

That decision opens the door for second-year wideout Luther Burden to step into a much larger role on offense.

Burden already entered the league with expectations as a dynamic playmaker. Now, the opportunity is even bigger.

He enjoyed a productive rookie season with 47 catches, 652 yards, and two touchdowns.

Loser: Caleb Williams

While the Bears strengthened their defense, the situation around Williams remains a concern.

Chicago lost starting center Drew Dalman, and the team’s trade for Garrett Bradbury represents a noticeable downgrade in terms of overall stability.

The offensive tackle situation also remains unsettled, with no long-term answer clearly in place at left tackle.

For a franchise quarterback entering a critical stage of his development, those questions up front are difficult to ignore.

Loser: Montez Sweat

Sweat remains the centerpiece of Chicago’s pass rush, and that’s exactly the problem.

Despite speculation about potential upgrades, the Bears have not yet added another major edge rusher. That means opposing offenses will likely continue focusing their protection schemes on slowing down Sweat.

Until Chicago adds another consistent pass-rush threat, Sweat will continue carrying the burden of being the defense’s primary disruptor.

Loser: The Bears' Offensive Line

If there’s one position group that still feels unsettled after the first wave of free agency, it’s the offensive line.

Between the downgrade at center and lingering questions at tackle, Chicago’s offensive line could remain one of the biggest storylines heading into the 2026 season.

And if the Bears want to remain contenders in the NFC North, solving that issue will be critical.

Chicago strengthened its defense and added depth across several areas of the roster. But as the offseason continues, the spotlight will remain on the offensive line and whether the Bears can give Williams the protection needed to lead another division title run.