7 Bears Entering Contract Years Who Won't Survive the 2027 Cap

The Chicago Bears massively improved the competition across their roster this offseason. However, they also had to make some tough decisions along the way. This year's roster will look much different than the 2025 squad, as they opted not to bring back a few key free agents this offseason (on top of trading another).

They appear destined to undergo a significant amount of roster turnover next offseason, as well. They have a few noteworthy players entering a contract year, and it's safe to assume they won't be able to bring many of them back with a new Caleb Williams contract on the horizon.

The Bears' brass have a few difficult decisions to make next offseason. How will the roster shake-up shake out at that time?

Garrett Bradbury: One and done

The Bears liked Garrett Bradbury enough to trade a fifth-round pick for his services shortly after Drew Dalman's sudden retirement. However, they didn't like him enough to avoid prioritizing landing the top center in this year's class with the selection of Iowa's Logan Jones with the 57th pick.

Bradbury always seemed like a one-year rental, as he is entering the final year of his contract, but the addition of Jones really cemented that fact. He will definitely be finding a new team next offseason, and might be relegated to backup duties in short order for the first time in his seven-year career.

Braxton Jones: Definitely gone

Braxton Jones entered last season in a similar position to the one that Garrett Bradbury enters this season. He was entering a contract year, and the Bears drafted their hopeful left tackle of the future via the selection of Ozzy Trapilo with the 56th pick. Jones got the first crack at the starting job, but they gave him the quick hook after he struggled early in the year.

Honestly, I was surprised when the Bears re-signed him this offseason. I thought for sure he was a goner, and he certainly would've been if Trapilo's status for 2026 wasn't in doubt after suffering a torn patellar tendon in their wild card matchup against Green Bay. Jones has definitely entered his one last ride era in the Windy City.

Noah Sewell: Definitely gone

Noah Sewell is coming off the best season of his career. While he struggled mightily against the pass, he was rock-solid on early downs in 2025. He outperformed expectations after failing to ascend beyond special teams over the first two years of his career.

Sewell tore his Achilles in Chicago's Week 17 matchup against San Francisco, but I honestly don't think he'd stick around even if he were fully healthy. He doesn't have enough speed to become anything other than a replacement-level starter in the modern NFL. The selection of Keyshaun Elliott could even be the death knell to his chances of providing anything on the defensive side of the ball next season.

Tyrique Stevenson: Definitely gone

Speaking of death knells, that is exactly what the selection of Malik Muhammad was for Tyrique Stevenson's future in Chicago. He was probably a goner regardless after failing to show an ounce of consistency over his first three seasons, but that selection really hammered that fact home.

The 25-year-old still has the inside track at the starting job opposite Jaylon Johnson, but his leash is even shorter than it was last year (when previous practice squader Nahshon Wright pushed him out of the lineup). The flashes will probably get Stevenson paid much more than he should be on the open market, and the Bears definitely won't be the team that puts pen to paper in that regard.

The Bears can afford to move on from high-upside starters like Stevenson because they are banking on Rome Odunze providing a massive ROI on his rookie deal. If Odunze can make that jump, the Bears' transition to a high-priced Caleb Williams era becomes much more sustainable.

Kalif Raymond: Probably gone

Kalif Raymond, whom the Bears signed to a one-year, $3.5 million deal this offseason, will have a role on both offense and special teams for Chicago in 2026. However, the Bears already drafted his hopeful replacement in Zavion Thomas in the third round of this year's draft.

If Raymond has a resurgent year (in either the receiving or return game) and Thomas fails to live up to his third-round draft slot, then Raymond could be brought back on another cheap deal. However, I ultimately think that's unlikely. At the age of 31, with Thomas waiting in the wings, he seems destined to be another one-and-done with Chicago.

Gervon Dexter: Probably gone (barring a surprising breakout)

Gervon Dexter is definitely in a similar position to Tyrique Stevenson when it comes to how their careers have panned out so far. However, he has at least shown semi-consistent promise in the pass-rush department. His 13.5 career sacks are actually tied with Jalen Carter, who was selected 44 picks earlier in the 2023 NFL Draft and is widely considered one of the best DTs in the league.

However, the pass-rush department is only half the battle for defensive tackles. Dexter has failed miserably in the other half. He's a complete non-factor against the run. The fact that they didn't prioritize the defensive tackle position in this year's class is the only thing keeping me from saying that he's definitely a goner. If he has a breakout season, I could see them re-signing him to a one-year extension. Definitely don't hold your breath on that one, though.

D'Andre Swift: Could go either way (but he definitely has the best odds)

D'Andre Swift is going to be 28 years old when he hits free agency. While that would still be in the prime of his career for virtually every other position, you generally don't want to re-sign a depreciating asset. However, there's some reason to believe he might still have some mileage left on his tires after carrying the ball only 364 times over his first three seasons.

Swift is also coming off the best season of his career with nearly 1400 yards from scrimmage and ten total touchdowns. I could definitely see a scenario where they keep him in Chicago on a two-year deal if he has another standout performance in 2026. He should have much greater value to the Bears than he would for a team looking for some new blood in free agency. That theoretically would make it easier to get a deal done if they want to go that route.

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