Bears Linked to Potential Blockbuster Deal for All-Pro Playmaker

Caleb Williams, Chicago Bears

The Chicago Bears have a clear need and, as a team ready to win now, know that a trade could be the best path forward to address it. They have already been linked to multiple trades that would send players out. But there has been far less on whom they might try to acquire, especially when it comes to addressing that looming need.

That could be about to change.

The Bears are among the teams linked to Las Vegas Raiders star Maxx Crosby, who has praised quarterback Caleb Williams. There could soon be movement regarding the five-time Pro Bowler and two-time Second Team All-Pro.

Bears Linked to Maxx Crosby Trade Before Offseason

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“I’d lean toward a Maxx Crosby trade happening, and maybe this week. But there’s going to have to be some needle-threading,” Sports Illustrated’s Albert Breer wrote on March 2, noting his belief that both sides want to avoid a drawn-out process in the public eye. “Vegas, to be sure, isn’t going to give Crosby away.”

“We should know soon enough which path the Raiders are taking, with teams like Dallas, Chicago, Baltimore, Buffalo, New England, Philadelphia and the Rams keeping tabs on his availability.”

ESPN’s Jeremy Fowler reported that it was a “layered discussion.”

“A team source said a few weeks ago that Crosby’s chances of returning were relatively small. But he doesn’t plan to request a trade,” Fowler wrote on March 1.

“He wants to win, which might not be in the cards for Las Vegas in 2026. Some teams I’ve spoken to believe he will remain with the Raiders — for now. “Why would you trade him?” one GM asked. “He’s a premier player at a premier position.” Added an executive from an NFC team: “I think the price is too high. I’m not sure they really want to move him at this point. But that could change.”

Fowler added that “at least a dozen teams” have registered interest in a trade for Crosby, echoing Breer’s sentiments that the haul is likely to be less than some other recent blockbusters due to Crosby’s age and recent injury history.

He also has a $35.8 million cap number in 2026.

Notably, Crosby’s cap hit will decrease when he officially begins his three-year, $106 million extension that runs through 2029.

However, with no guaranteed money on that deal, there is at least a minor chance that Crosby seeks some kind of re-work. The Bears will have to get creative to make room for Crosby this season.

Their potentially having to figure his future out would only add another layer of complexity.

Bears Could Have Pair of Trade Chips for Raiders

Speculation around the Bears landing Crosby is not new, and it often includes wide receiver DJ Moore, who general manager Ryan Poles acknowledged could be traded this offseason.

However, Fowler noted that the Raiders are interested in linebacker Tremaine Edmunds.

Including Edmunds and Moore in a trade package for Crosby would clear more than enough space for the Bears, whereas the Raiders have the second-most headroom in the NFL before the official start of the offseason on March 11.

That could ease the burden of draft capital from both standpoints, leaving something like the framework below.

Bears get:

  • Maxx Crosby

Raiders get:

  • DJ Moore
  • Tremaine Edmunds
  • 2026 first-round pick (No. 25 overall)
  • 2027 second-round pick

This deal would give both sides what they need and/or on paper.

Draft compensation still looms as the most likely sticking point in a trade for Crosby or any other target the Bears have in mind, as they balance winning now with their long-term financial flexibility.

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