The Chicago Bears are soon expected to enter into the offseason that will be filled with numerous tough decisions needed to be made.

Beyond the expected decisions to be made with the coaching staff, quarterback position, and the 2024 NFL Draft process, the Bears will also have to make some tough decisions with other players currently on the roster.

The Bears will enter into the offseason with $62,155,851 in cap space, which ranks 7th in the league, according to Spotrac. It's quite a sum to have readily available to spend, but the Bears could increase that number even higher by making a couple of decisions regarding players on the current roster in 2024.

Looking ahead to the Bears 2024 books, here's the players with the highest cap hits on the roster entering next season:

DE Montez Sweat- $25,085,200
LB Tremaine Edmunds- $22,437,500
S   Eddie Jackson- $18,140,000
WR DJ Moore- $16,050,000
OG Cody Whitehair- $13,250,000

Based on the team's expected highest cap hits in 2024, here's the two players who should potentially be cap casualties for the Bears heading into the offseason.

Eddie Jackson

This one could be a tough pill to swallow for Bears fans. The team's veteran safety has been a force in Chicago's secondary for years but time is starting to catch up to Eddie Jackson. Heading into Year 8, an $18.1 million cap hit is simply too high of a price to pay just to have an experienced player in the backend of the defense.

Jackson's experience is the primary reason Bears general manager Ryan Poles and head coach Matt Eberflus decided to retain the veteran safety during the 2023 season, but it could be a different story in 2024.

"He's been great," Eberflus said back in December. "He's been awesome in the room and he's been great with the young guys. I think it was really beneficial for [Kyler] Gordon, [Jaquan] Brisker, and those young secondary pieces to be able to see a veteran operate that way. And then, this year we added two more pieces to it. I think that's always great to have that veteran presence in there."

Having Jackson on the roster in 2023 was certainly beneficial for those young guys but now those players are developing into leaders themselves, especially Brisker. Week 18's season finale could be the passing of the torch at the position.

If the Bears were to move on from Jackson this offseason, the team would only have to eat $3.9 million in dead cap as a post-June 1st designation. It's certainly possible and the Bears will free up a lot more cap space to invest elsewhere while finding a new replacement at the position in the draft.

Cody Whitehair

Cody Whitehair is another likely candidate the Bears could elect to move on from heading into 2024 in order to free up more cap space. Currently, Whitehair has a $13.25 million cap hit in 2024, which ranks 5th on the team and 1st among the Bears offensive linemen.

Whitehair as had a disappointing 2023 season after being used at both guard and center but has mainly been a plug-and-play depth player since Teven Jenkins returned. His price tag is entirely to high for a non-starter to take up and the Bears should likely be moving on from him this offseason.

According to Pro Football Focus, Whitehair has a 44.1 run blocking grade and a 55.2 pass blocking grade in 2023. In pass protection, Whitehair has given up three sacks and 20 pressures on 438 pass blocking snaps. The Bears can easily find a cheaper and more productive replacement elsewhere in 2024.

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