Bears Have 6 Contract-Year Players Who May Be Gone by 2027

As things stand now, the Chicago Bears have over 30 players who are in a contract year in 2026.

Among those players are several important ones on both sides of the ball who figure to make at least some semblance of a significant impact this coming season.

But, based on how we see things, six of those important players are not going to be back in 2027. Here's who they are and why.

D'Andre Swift

Swift has been effective over two seasons as the Bears' lead back, but Kyle Monangai's emergence gives Chicago a potential cheap replacement for the veteran at RB1 in 2027.

Even if Monangai takes a step back, there's a good chance the Bears still opt to go in a different direction and let Swift walk in order to save some money and allocate resources elsewhere.

Braxton Jones

Jones will be one of the competitors for the starting left tackle job vacated by the injury to Ozzy Trapilo and all signs point to him being the favorite to win that job.

Jones has a golden opportunity to have a bounce-back year and show he's a starting-caliber left tackle in this league after getting benched last season. We think he accomplishes that, but the return of Trapilo leads to Chicago letting Jones walk in 2027.

Garrett Bradbury

Bradbury was the Bears' solution to the unexpected retirement of Drew Dalman, but there was always a chance he wouldn't be more than a one-year solution given his contract situation that makes him a free agent in 2027.

Now that the Bears have drafted Logan Jones in the second round of the 2026 NFL Draft, Bradbury's odds of staying in Chicago beyond this coming season have become extremely small.

Gervon Dexter

Dexter has the potential to be a true force on the interior of the defensive line given his pass-rush prowess, but the veteran is lacking as a run defender.

Someone is going to pay Dexter good money in 2027 because of his ability to get after the quarterback, but we don't see the Bears being that team unless he greatly improves his run defense. We're skeptical Dexter can, thus the Bears are going to let him leave.

Tyrique Stevenson

Stevenson saw a reduced role in 2025 after struggling, and now he's fighting for a starting job against fourth-round pick Malik Muhammad in 2026.

Maybe Stevenson begins the year as the team's starter, but we're not sold on him staying as the CB2 for all 17 games. Even if he can do that, the Bears are not going to shell out another significant contract for a cornerback and instead will turn to Muhammad.

Kalif Raymond

The Bears killed two birds with one stone by signing Raymond, who adds a much-needed veteran presence to the wide receivers room while also improving the return game.

But the Bears drafted a similar player in Zavion Thomas in the third round, which will lead to Raymond being a one-year stopgap before Thomas takes over his duties in 2027.

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