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10 Major Contract Extensions The Bears Must Address

Several crucial contract extensions await the Chicago Bears front office, presenting them with difficult decisions in the near future.
Bears contract extensions

The Chicago Bears overhauled the entire roster when Ryan Poles was hired as the Bears GM in 2022. Now, with key pieces of the team in line for a major contract extension, there will be some tough decisions awaiting the Bears front office. Who should the Bears re-sign and let go?

10 Major Contract Extensions The Bears Must Address

2025 Free Agents

Keenan Allen, WR

Keenan Allen was recently traded to the Bears for a fourth-round pick. The longtime Charger has been Mr. reliable on the field, amassing several 1,000-yard seasons and consistently being hailed as one of the top wide receivers in the league. He’ll be a huge help for rookie quarterback Caleb Williams and should be a difference-maker on the field for the Bears.

Contract Projection: 1yr, $21 mil

Teven Jenkins, OG

Teven Jenkins has been dominant on the field but struggles to stay healthy. Despite playing at a high level across multiple positions on the offensive line, Jenkins has missed multiple games each season and has yet to play an entire season. With contract negotiations at a standstill, the front office may face its first difficult decision in potentially letting Jenkins enter free agency.

Khalil Herbert, RB

As a sixth-round pick, Khalil Herbert has exceeded expectations. He’s filled the void left by David Montgomery and emerged as the Bears’ featured back. However, his inconsistencies in pass-blocking, coupled with the recent signing of D’Andre Swift, could indicate the end of Herbert’s time in Chicago.

Jack Sanborn, LB

Jack Sanborn, also known as “Sand Man,” has quickly become a fan favorite. Arguably, the Bears’ most underrated player, his tackling ability and football IQ have allowed him to earn a spot on the roster and become the Bears starting strongside linebacker. At 23 years old, Sanborn has time to improve and become the next great Bears linebacker.

Contract Projection: 3yr, $16 mil

2026 Free Agents

D.J. Moore, WR

D.J. Moore is currently the 17th highest-paid wide receiver in the NFL. A steal for the Bears, given he is easily one of the league’s top receivers. A superstar wide receiver deserves to get paid, and the Bears should do everything possible to ensure Moore remains in a Bears jersey.

Contract Projection: 3 yr, $93 mil

Nate Davis, OG

Nate Davis signed a massive contract in 2023 and was supposed to be a huge addition to the team. However, with missed practices during the offseason dealing with family issues, Davis underperformed last season and missed time due to an ankle injury. In addition, Davis has started the 2024 offseason practicing in a limited capacity, raising questions about his commitment to the team. If he continues this trend, the Bears will look elsewhere to replace Davis.

T.J. Edwards, LB

T.J. Edwards has been the best free-agent signing by Ryan Poles and has been the heartbeat of the Bears defense. His intuitive ability to be everywhere on the field allows the rest of the team to perform at a higher level. Edwards is one of the best linebackers in the NFL and deserves to get paid.

Contract Projection: 2 yr, $30 mil

Braxton Jones, OT

Playing in one of the most important positions in football, left tackle Braxton Jones has done a solid job protecting the quarterback. He’s been improving every game and has exceeded expectations. The pressing question is whether the Bears should invest heavily in Jones or give 2024 third-round pick Kiran Amegadije a chance to become their next left tackle. With other key contracts to consider, the Bears might decide to let Jones enter free agency.

Kyler Gordon, CB

Kyler Gordon, Ryan Poles’ first draft pick as Bears GM, has made significant strides over the past two seasons. He has emerged as one of the NFL’s top slot cornerbacks and is on track for a substantial payday.

Contract Projection: 3 yr, $33 mil

Jaquan Brisker, S

Jaquan Brisker has been a dependable safety for the Bears, tallying over 100 total tackles in each of his two seasons with the team. He has quickly become a leader, bringing the energy on defense. Brisker should be a cornerstone of the Bears defense for a long time.

Contract Projection: 3 yr, $19.5 mil

Main Image: Matt Marton – USA Today Sports


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