The Chicago Bears have emerged as heavy favorites to land Las Vegas Raiders pass rusher Maxx Crosby, and multiple reports suggest a deal could happen before free agency opens next week.
According to BetOnline, Chicago sits at -140, ahead of the Bills (+500), Patriots (+600), Ravens (+750), and Cowboys (+800). The betting market is not alone. Insider reporting and Crosby’s own signals increasingly point toward the Bears.
How It Fell Apart in Las Vegas
Crosby’s availability stems from a breakdown in alignment.
Last December, Raiders GM John Spytek informed the five-time Pro Bowl edge rusher that the team was shutting him down for the final two games. The decision secured draft positioning, but it did not sit well with one of the league’s most competitive players. Las Vegas finished 3-14 and secured the first overall pick, yet the move strained its relationship with the emotional engine of its defense.
That tension reflects a broader disconnect. As detailed in The Athletic, Crosby once had to be warned by Jon Gruden to ease up in practice after repeatedly hitting quarterbacks. He was told that if he could not dial it back, he risked being cut.
That edge defines him. It also makes tanking environments a difficult fit.
Instability has marked his tenure with the Raiders. Including interim coach Rich Bisaccia in 2021, Crosby has played under five head coaches. Newly hired Klint Kubiak would be his sixth. The Raiders have produced just one winning season during that span.
Trust issues extended beyond coaching turnover.
Questions surfaced about the influence of Alex Guerrero, officially the team’s wellness coordinator and a longtime Tom Brady associate. Guerrero attends practices and meetings and, according to reports, has informed players of pending transactions and suggested staff roles could be affected if his guidance was ignored. With Brady based primarily in Florida, Guerrero has operated as a conduit inside the building.
That structure did not inspire universal confidence among veteran players.
After firing Pete Carroll in January, owner Mark Davis handed full football authority to Spytek and Brady to operate jointly. Their first defining decision revolves around Crosby.
A Trade Is Coming…The Question Is When
With Las Vegas preparing to draft Indiana quarterback Fernando Mendoza first overall, moving Crosby aligns with a long-term reset. The Raiders can convert a premier veteran into draft capital to accelerate that rebuild.
The interest in Crosby is substantial. Roughly half a dozen teams inquired about Crosby at last year’s NFL Combine. This year, that number has grown.
The Raiders are seeking a return comparable to what Dallas received from Green Bay for Micah Parsons last August: two first-round picks and Pro Bowl defensive tackle Kenny Clark. Crosby turns 29 next summer and recently underwent meniscus surgery. While those factors complicate his trade value, they have not reduced demand.
Sports Illustrated’s Albert Breer indicated a trade could materialize quickly. ESPN’s Jeremy Fowler reported a team source called it “relatively small” that Crosby returns to Las Vegas.
The Athletic’s Dianna Russini added that the outcome will “come down to what Maxx wants.”
What Maxx wants appears to be Chicago.
Why Chicago Makes Sense
KOA Colorado’s Benjamin Allbright reported the Bears are Crosby’s preferred destination if he has input. The remaining hurdle is how the extension would be structured.
Crosby’s appearance on Caleb Williams’ podcast only amplified speculation. He spoke openly about his respect for Williams and the trajectory of the Bears.
The football need is clear. Chicago ranked 22nd in the NFL with 35 sacks in 2025. Montez Sweat led the team and became the first Bear since Robert Quinn in 2021 to record double-digit sacks. But he operated without a consistent counterpart.
Crosby posted 10 sacks and 28 tackles for loss in 2025 despite playing through injuries. His 28 tackles for loss ranked second in the NFL. ESPN’s Bill Barnwell noted that pairing Crosby with Sweat would prevent offenses from routinely sliding double teams in one direction.
The Trade Framework and Cap Math
The most discussed structure centers on wide receiver DJ Moore. Jeremy Fowler outlined a package sending Moore, Chicago’s 2026 first-round pick (No. 25 overall), and a 2027 third-round pick to Las Vegas for Crosby.
For the Raiders, Moore gives Mendoza an immediate No. 1 target and the draft capital fuels the broader rebuild.
For Chicago, moving Moore shifts the offensive core toward Rome Odunze, Colston Loveland, and Luther Burden III alongside Williams. It also frees roughly $16.5 million in cap space to help absorb Crosby’s three-year, $106.5 million extension.
Additional flexibility exists. The retirement of center Drew Dalman clears approximately $10 million. A trade or release of linebacker Tremaine Edmunds could push available space toward $25 million. The numbers are tight but workable.
The final variable is Bears GM Ryan Poles. He has been disciplined with premium draft capital, conscious of the aggressive strategy employed by former GM Ryan Pace. It would be the boldest move of his tenure.
Bottom Line
Crosby has spent his career setting a relentless standard inside a franchise that rarely risen to his level. Now, with the Raiders resetting around Mendoza and insiders anticipating movement, the window is open.
The Bears have the need and the assets to get a deal done.
The question is whether Chicago is ready to match his urgency.
