Colin Cowherd Urges Chicago Bears to Trade for Maxx Crosby

The Chicago Bears enter the final days before the 2026 NFL free agency period with a suddenly shifting offseason plan.

The unexpected retirement of Drew Dalman created an immediate hole on the offensive line and forced general manager Ryan Poles to reassess priorities. But another storyline continues to dominate the conversation around Chicago’s offseason: whether the Bears should pursue a blockbuster trade for Maxx Crosby.

One national voice believes the answer should be obvious.

Why Colin Cowherd Believes Chicago Should Make a Move for Maxx Crosby

Colin Cowherd recently discussed the idea of Chicago making an aggressive move for Crosby on The Herd, arguing that the Bears are in a position to pursue an elite defender.

“Go for it. Ben Johnson's an aggressive guy. Ryan Poles is an aggressive GM. Go for it," Cowherd said. "It's the number one need, edge pressure. It's not a roll of the dice. He's an elite player. Leads the NFL since he entered in tackles for losses. He's two years younger than Myles Garrett, who was just the defensive player of the year.”

Cowherd’s argument centers on a simple point: players of Crosby’s caliber rarely become available, and teams that believe they are close to competing should act decisively.

Drew Dalman’s Retirement Highlights the Bears' Urgency

Cowherd also pointed to Dalman’s retirement as a reminder of how quickly circumstances can change in the NFL.

“Drew Dalman, who they just paid a fortune to last year, retired. At 27, he's like, ‘Yeah, I'm done.’ Interior O-lineman beat you up physically. I'm done. And so the Bears with Caleb Williams were the number one pass-blocking unit and the number seven run-blocking unit, and anchoring that was this great center from the Falcons that they made a deal for a year ago, Drew Dalman. He just retired. And so you only got two years left with Caleb Williams on the rookie deal. He's going to get expensive real quick.”

His broader message was clear: roster stability in the NFL is never guaranteed. Teams that believe they have a competitive window should capitalize before circumstances shift.

Why Maxx Crosby Continues to Be Linked to Chicago

Crosby would address one of the Bears’ most discussed defensive needs: consistent edge pressure opposite Montez Sweat.

Sweat led Chicago with double-digit sacks in 2025, but offenses often focused protection on him without facing a comparable threat from the opposite side. Adding Crosby would dramatically change that dynamic and give the Bears one of the NFL’s most disruptive pass-rush duos.

Few defensive players impact games the way Crosby does. His relentless motor, ability to win with power and technique, and consistent backfield penetration have made him one of the league’s premier edge defenders.

The Trade Cost Could Be the Biggest Obstacle

The largest hurdle in any Maxx Crosby deal is compensation.

Several NFL insiders have reported that the Las Vegas Raiders could seek two first-round picks in return for their star defender. That type of price would represent a major investment for Chicago.

However, trade negotiations rarely begin and end with the same terms. If the Raiders become more flexible, potentially considering a package involving draft capital and an established player such as DJ Moore, discussions could become more realistic.

What Happens Next for the Chicago Bears

For now, a Maxx Crosby trade remains speculative.

But Chicago’s name continues to surface whenever league insiders and analysts discuss potential landing spots. When the same connection appears repeatedly across national conversations, it often signals genuine league-wide belief that a deal could make sense.

With free agency approaching and the roster still evolving after Dalman’s retirement, the Bears face a defining question for the 2026 offseason.

If an opportunity to acquire Maxx Crosby becomes real, will Chicago be willing to make the move?