Chicago added several key pieces to Dennis Allen’s defense in the opening wave of free agency, and the way those contracts are structured could still leave room for more roster upgrades.
The Chicago Bears were far from the NFL’s most aggressive team on the opening day of free agency as the league’s legal tampering window opened Monday.
Still, Chicago managed to make several meaningful moves that pushed the roster in the right direction as the team continues building toward the 2026 season.
The Bears added an infusion of talent to Dennis Allen’s defense, beginning with the return of linebacker D’Marco Jackson on a two-year deal worth up to $10.5 million. Jackson previously played for Allen during their time together with the New Orleans Saints and emerged as one of Chicago’s most pleasant surprises in 2025 after stepping in for the injured Tremaine Edmunds.
Jackson may not be guaranteed a starting role heading into next season, but given the uncertainty surrounding T.J. Edwards and the Bears’ need for additional linebacker depth, retaining him was one of Chicago’s most logical offseason priorities.
The Bears also added defensive lineman Neville Gallimore and made two splashier defensive signings: Super Bowl champion safety Coby Bryant, who agreed to a three-year, $40 million contract, and linebacker Devin Bush, who landed a three-year deal worth $30 million.
While I’m bullish on several of these players and how they fit within Allen’s defensive system, each move initially came with at least a little concern.
The Bears don’t have an endless supply of salary cap space, and for a moment it felt as though Chicago might struggle to address all of its roster needs after committing significant money at safety and linebacker.
Those concerns only intensified when the Bears agreed to a one-year deal with left tackle Braxton Jones, a contract worth $5 million with the potential to reach $10 million through incentives.
However, once you dig into the details, the structure of these contracts actually gives the Bears more financial flexibility than it first appears — leaving the door open for additional roster upgrades.
Bryant’s contract, for example, is heavily backloaded. His base salary in 2026 sits at just $1.5 million before jumping to $12.25 million in 2027. After factoring in his prorated signing bonus and other minor bonuses, Bryant’s cap hit for the upcoming season drops to just $5.96 million, a remarkably manageable figure for a player on a $40 million contract.
Jackson’s deal follows a similar philosophy. His base salary for the 2026 season is only $1.75 million, and the contract is heavily incentive-based. When combined with a relatively modest signing bonus, Jackson’s cap hit comes in at just over $3 million for 2026 despite the deal having a maximum value north of $10 million.
The same concept applies to Jones’ contract. The Bears will carry roughly $5 million on their cap for Jones in 2026, while the additional $5 million in incentives likely won’t impact the cap until 2027 — if they are earned at all.
That distinction exists because the NFL categorizes incentives into two groups: Likely To Be Earned (LTBE) and Not Likely To Be Earned (NLTBE).
LTBE incentives count against the current year’s cap because the player achieved those benchmarks the previous season. NLTBE incentives, however, do not count against the current cap and instead apply to the following year if the player earns them.
Because Jones battled injuries, was benched, and struggled during portions of the 2025 season, it’s highly unlikely his incentives will be classified as LTBE. As a result, those bonuses probably won’t affect Chicago’s 2026 cap at all.
That kind of structuring appears intentional. The Bears project to have significantly more cap flexibility in 2027, when several large dead-money charges finally come off the books.
Prior to the agreement with Jones, Chicago had $14.96 million in total cap space and $10.28 million in effective cap space, though those figures were still pending finalized cap hits for linebacker Devin Bush and newly signed quarterback Case Keenum, whose contract details have not yet been fully reported.
Once those numbers are finalized, the Bears will likely appear to be tight against the cap.
But appearances can be deceiving.
Chicago still has several avenues available to create additional financial breathing room. Trading quarterback Tyson Bagent would free up roughly $3.75 million in cap space, and restructures involving players such as Montez Sweat, Joe Thuney, Jaylon Johnson, and Cole Kmet could collectively create as much as $30 million in additional flexibility.
That may be all the Bears need to address their remaining roster holes.
At this point, Chicago’s biggest needs include another safety — potentially a reunion with Kevin Byard — along with help at cornerback, edge rusher, and wide receiver.
Realistically, the Bears won’t be able to solve every remaining issue in free agency. That’s what the NFL Draft is for.
But if Chicago can check even two more boxes before April, Bears fans should feel pretty good about the foundation the front office has laid during the opening wave of free agency.