Five Chicago Bears players are uncertain going into the offseason.

The Chicago Bears enter the 2024 offseason with a number of important decisions to make as they continue their rebuilding process under General Manager Ryan Poles and Head Coach Matt Eberflus. After a season marked by both progress and frustration, the Bears will need to focus on their most pressing needs and determine which players fit into the long-term plans for the team.
While there are clear pieces on the roster that will be part of the team’s future, there are also players whose futures are uncertain. These players face questions regarding their role, contracts, and overall fit within the Bears’ rebuilding project. Some have shown flashes of potential, while others have been inconsistent, and it is unclear if they will remain in Chicago’s plans moving forward.
In this article, we will take a look at five key players whose futures with the Bears are uncertain as they head into the 2024 offseason. These players are at critical junctures in their careers, and the Bears must decide whether they are worth keeping or whether it’s time to move on.
1. Darnell Mooney – Wide Receiver
Overview:
After an impressive rookie season in 2020, Darnell Mooney quickly became one of the bright spots on the Bears’ offense. As a second-year player in 2021, Mooney established himself as a reliable target in the passing game and flashed big-play potential. However, in 2023, his performance was impacted by injuries and inconsistent quarterback play. Despite a productive season statistically, Mooney has not fully lived up to the expectations of a No. 1 receiver.
Uncertainty:
Mooney’s future with the Bears is currently in question. Although he has had moments of brilliance, he has not yet developed into the true No. 1 receiver that many hoped for. His 2023 campaign, which was marred by injuries and a lack of consistency from the quarterback position, saw him post decent numbers but not enough to make him indispensable. As the Bears continue to develop their offense around Justin Fields, they may need a more consistent and dynamic receiving threat to complement their young quarterback.
Mooney is also entering the final year of his rookie contract. With a deep wide receiver class in the 2024 NFL Draft and plenty of veteran options available in free agency, the Bears may decide to either trade Mooney or let him walk after the 2024 season, particularly if they don’t see him as part of their long-term plans.
The question is whether Matt Eberflus and Ryan Poles see Mooney as a valuable building block or as a player who is expendable in the pursuit of more dynamic and reliable receiving talent.
2. Khalil Mack – Edge Rusher
Overview:
Khalil Mack was one of the most exciting acquisitions for the Bears during the 2018 offseason when the team traded for the All-Pro edge rusher from the Oakland Raiders. Over his first few seasons with the Bears, Mack was a dominant force, regularly finishing as one of the top sack leaders in the NFL and being a critical part of the Bears’ defense. However, injuries and age have started to catch up with him. Mack is now on the wrong side of 30, and his production has been inconsistent over the past two seasons.
Uncertainty:
Mack is still a highly respected and talented pass rusher, but the Bears must evaluate whether it makes sense to keep him around, especially given his contract and the direction of the team. Mack’s contract could be an issue, as the Bears may not want to allocate a significant portion of their salary cap to a player who is no longer as dominant as he once was. He’s still a capable edge rusher but has not been able to stay healthy over the past two seasons, and with younger players like Trevis Gipson and Dominique Robinson showing promise, Mack’s future with the team is unclear.
Another factor that makes Mack’s future uncertain is the Bears’ rebuilding focus. The team is not expected to contend for a Super Bowl in 2024, so they may decide to part ways with veterans like Mack in favor of building younger talent. If the Bears elect to go this route, they could free up significant cap space and look to develop younger pass rushers who could contribute long-term.
Given his age, injury history, and contract, it’s possible that the Bears could trade Mack or even release him in the near future, allowing them to shift their focus to younger players in the edge rusher position.
3. Cody Whitehair – Offensive Guard
Overview:
Cody Whitehair has been a mainstay on the Chicago Bears’ offensive line since he was drafted in 2016. Known for his versatility and leadership, Whitehair has been the anchor of the Bears’ interior offensive line. He has consistently started at left guard and center and has been an essential piece of the team’s offensive line for years. However, over the past few seasons, Whitehair’s performance has been inconsistent, and injuries have also taken a toll on his effectiveness.
Uncertainty:
Whitehair’s contract status and his recent decline in performance are the primary reasons for uncertainty surrounding his future in Chicago. The Bears have already begun to prioritize improving the offensive line, and Whitehair’s $8 million salary for 2024 may be seen as an expensive price to pay for a player who is not performing at the elite level that the Bears expect.
Additionally, the Bears have already invested in their offensive line with players like Teven Jenkins and Braxton Jones, and they may be looking to further improve their line during the draft or free agency. Whitehair’s age and recent injury issues could make him expendable in the eyes of the Bears’ front office, especially if they plan to revamp their offensive line with younger, more durable players.
If the Bears feel that Whitehair’s best years are behind him or if they can find a younger replacement through free agency or the draft, it would not be surprising to see Whitehair released or traded in the offseason. However, his leadership and experience on the line could still make him an appealing option to retain, albeit at a lower salary or in a backup role.
4. David Montgomery – Running Back
Overview:
David Montgomery has been a staple in the Bears’ backfield for the past few seasons, providing consistent production as a bruising, between-the-tackles runner. Known for his vision, toughness, and ability to pick up yards after contact, Montgomery has been one of the more reliable players on the offense despite the team’s struggles. However, his time in Chicago is uncertain due to the emergence of younger players and the possibility of the team looking for a more explosive playmaker at running back.
Uncertainty:
Montgomery is set to be a free agent in 2024, and the Bears will need to make a decision on whether to re-sign him or let him walk. With Khalil Herbert showing potential in 2023, Montgomery’s role in the offense could be reduced. While Montgomery is a reliable player, he may not provide the same level of game-breaking ability as other top-tier running backs in the league, and the Bears could choose to move in a different direction.
The Bears will also have to consider the financial side of things. Running backs are often viewed as replaceable, and the Bears may prefer to invest their money in other areas of the team. If Montgomery’s market value is too high, or if the Bears feel that Herbert and other running backs can take on a larger role, it is possible that Montgomery will not return to the team in 2024.
Ultimately, Montgomery’s future with the Bears will depend on both his value to the team and the direction the Bears want to take at the running back position. If they want to upgrade at the position with a younger or more dynamic player, they could let Montgomery walk.
5. Eddie Jackson – Safety
Overview:
Eddie Jackson has been a cornerstone of the Bears’ defense for years, earning a reputation as one of the top ball-hawking safeties in the NFL. Known for his playmaking ability, Jackson has the vision and instinct to create turnovers, and he has been one of the team’s most consistent defensive players. However, his performance has been less impactful in recent seasons, and questions about his role in the new defensive scheme have begun to emerge.
Uncertainty:
Eddie Jackson is under contract for the 2024 season, but his future with the team remains uncertain. The Bears’ defense under Matt Eberflus is focused on creating turnovers and being more aggressive, but Jackson’s role has been inconsistent in recent seasons. He hasn’t been the same player since his 2018 All-Pro season, and while he still has the ability to make plays, his lack of consistency and struggle with injury concerns have raised questions about his long-term fit in Chicago.
Additionally, the Bears have the option to release Jackson and save some cap space, which could be an appealing option if they feel that younger players such as Jaquan Brisker or Kyler Gordon can handle a larger role in the secondary. If the Bears are looking to rebuild their defense with fresh talent or find a more consistent playmaker, Jackson could be a candidate for release or trade.