Ranking the best free agency moves Chicago Bears GM Ryan Poles has made so far

Since Ryan Poles took over as the General Manager of the Chicago Bears in January 2022, he has been tasked with leading the team through a critical rebuild. The Bears, while possessing a young and promising quarterback in Justin Fields, needed substantial improvements across nearly every position group. Poles has been active in addressing weaknesses, and one of the most important methods of shaping a team quickly is through free agency.

In just a couple of offseasons, Poles has made several bold and strategic moves that have impacted the direction of the Bears. Whether it was shoring up the offensive line, adding playmakers to the defense, or making moves to improve special teams, the decisions made in free agency have had a long-lasting impact. Below is a ranking of the best free agency moves Poles has made so far, starting from the most impactful to the moves that might still prove significant in the long term.

1. Signing DT Derrick Brown (2025) – A Game-Changer Up Front

Although the Bears’ defensive line was one of the stronger units on the roster, it lacked an interior pass rusher who could disrupt plays in the backfield. Enter Derrick Brown, a monster defensive tackle out of Auburn, who immediately became a cornerstone player for the team’s defensive front. His contract, which was among the highest in free agency for a defensive tackle, immediately made an impact on the Bears’ defense.

Why it’s impactful: Brown’s ability to generate pressure on the quarterback from the inside is crucial to the success of any defense, and with an already talented defensive line featuring players like Robert Quinn and Roquan Smith, Brown’s presence takes the pressure off the edge rushers and helps disrupt quarterbacks from the middle. He is a big-bodied tackle who demands double teams, freeing up other players to make plays. As the Bears continue to develop their defense, having someone like Brown who can collapse the pocket from the interior and stop the run is invaluable.

2. Signing OL Cody Whitehair (2025) – Stabilizing the Offensive Line

If there was one area that stood out as a clear weakness for the Bears, it was their offensive line. Despite solid play from left tackle Teven Jenkins, the interior of the line lacked consistency, and Justin Fields needed better protection. Enter Cody Whitehair, an experienced interior lineman who has anchored offensive lines throughout his career.

Why it’s impactful: Whitehair’s signing solidified the center position, giving the Bears a leader in the trenches to help protect Fields. Whitehair brings versatility and a steady presence to the offensive line. His leadership and ability to open holes for the running game helped elevate the Bears’ overall offensive performance in 2025. His experience also helps mentor younger players, ensuring they are prepared for the demands of the NFL. With an improving offensive line, the Bears were able to protect their franchise quarterback and open running lanes for David Montgomery and Khalil Herbert.

3. Signing CB Jamel Dean (2025) – Reinforcing the Secondary

The Bears’ secondary was a weak point for the team as they struggled to cover elite receivers in a division that has featured talented wideouts such as Justin Jefferson and DJ Moore. The addition of Jamel Dean to the defensive backfield brought immediate improvement to the Bears’ pass defense. Dean, a former Tampa Bay Buccaneer, has been one of the league’s best cornerbacks and an underrated force in the secondary.

Why it’s impactful: Dean is a shutdown corner who can play both press and off-man coverage, making him versatile in a variety of defensive schemes. His signing immediately gave the Bears a reliable cornerback who could handle top receiving threats in the NFC North. His ability to lock down the opposing team’s best receiver, while allowing the Bears’ other defenders to focus on other aspects of the defense, helped make the Bears’ secondary more formidable. With Dean in place, the Bears’ defense became more balanced, and the team’s ability to stop the pass became one of their strongest attributes.

4. Signing WR D.J. Chark (2025) – Giving Fields a Big-Play Threat

Another critical area of need for the Bears was the wide receiver position. Darnell Mooney had shown promise as a deep threat, but the team lacked a true No. 1 receiver who could complement Fields’ skill set. Poles addressed this issue by signing D.J. Chark to a contract that added a speedy, vertical threat to the receiving corps.

Why it’s impactful: Chark, who had a standout season in Jacksonville, is a perfect complement to Darnell Mooney and Fields’ skillset. Chark’s elite speed provides Fields with a reliable downfield weapon capable of stretching defenses and creating space for Mooney and tight end Cole Kmet. His deep-threat ability also opens up the running game for Khalil Herbert and helps keep defenses honest. Adding Chark helps elevate the Bears’ passing attack, providing Fields with an explosive option and giving the offense an immediate threat to work with.

5. Signing LB T.J. Edwards (2025) – Strengthening the Middle of the Defense

While the Bears have invested heavily in their secondary, the linebacker position was one area in which they struggled to make major improvements. To address this, Poles made a strong move by signing T.J. Edwards, one of the top free-agent linebackers in 2025. Edwards’ signing bolstered the Bears’ linebacker unit, which is critical in their 4-3 defense.

Why it’s impactful: Edwards brings a wealth of experience and high-level production to the middle of the defense. He’s a versatile linebacker who can cover the field, stop the run, and rush the passer when needed. His ability to read the field and make plays in the open field immediately made the Bears’ linebacker unit much stronger. Pairing Edwards with Roquan Smith gave the Bears two linebackers capable of playing in all situations, including pass coverage, and allowed Smith to play to his strengths as a sideline-to-sideline tackler. Edwards is an invaluable piece in both the passing and running game and provides veteran leadership in a young defensive unit.

6. Signing RB David Montgomery (2025) – Bolstering the Backfield

The Bears’ offense had significant potential, but they needed a solid, reliable running back to complement the dual-threat abilities of Fields. Poles made the decision to sign David Montgomery away from the division-rival Detroit Lions, adding a proven workhorse back to the offense.

Why it’s impactful: Montgomery is a tough, physical back who excels between the tackles and can grind out tough yards. His ability to handle a heavy workload and contribute as a pass-catcher out of the backfield gave the Bears an every-down back who could relieve some pressure off of Fields. Montgomery’s consistent yardage accumulation helped open up the passing game and establish balance in the offense. With Montgomery as a reliable option, Fields didn’t have to shoulder the load alone, and the Bears’ offensive attack became more versatile and dangerous.

7. Signing TE Austin Hooper (2025) – Enhancing the Passing Game

With the Bears looking to improve their passing game under Fields, the team needed a tight end who could be a consistent target and a security blanket in key moments. Austin Hooper was brought in to be the guy who could contribute as a blocker and pass-catcher in the Bears’ system.

Why it’s impactful: Hooper’s signing gave the Bears a reliable option at tight end, someone who could work the middle of the field and provide Fields with an easy target. He also added value as a blocker, helping in both the run game and in pass protection. Hooper’s experience and reliable hands helped open up the passing game, especially in short-yardage and red-zone situations. Though his role may not have been the flashiest, he was a steady contributor to a growing offense.

8. Signing S Jimmie Ward (2025) – Adding Experience to the Secondary

Poles continued to add veterans to the defense by signing Jimmie Ward, an experienced safety from the San Francisco 49ers. Ward was known for his versatility and ability to play multiple roles in the secondary.

Why it’s impactful: Ward’s ability to move between safety positions and cornerback made him a valuable addition to the Bears’ defensive backfield. His leadership and experience added stability to the Bears’ young secondary. Although he wasn’t a major splash signing, Ward’s role in the defense as a versatile, smart player gave the Bears valuable depth in a critical area.