Bear Digest

Maxx Crosby's Message to Caleb Williams Sparks Chicago Bears Trade Speculation

Maxx Crosby praised Caleb Williams on The Rush Podcast, and Bears fans are wondering if it hints at a 2026 move to Chicago.
Bryan Perez|
Las Vegas Raiders defensive end Maxx Crosby (98) looks on from the sideline.
Las Vegas Raiders defensive end Maxx Crosby (98) looks on from the sideline. | Kiyoshi Mio-Imagn Images

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Chicago Bears

Bears fans didn't need much to start connecting the dots between Maxx Crosby and Chicago, and after the latest episode of Crosby's "The Rush" podcast, which featured Caleb Williams as his guest, that line may have been drawn with a Sharpie.

At the end of the episode, Crosby delivered a glowing message to Williams.

“Just to be open and honest, bro, like we talked about earlier, but respect at a different level, bro. You’re one of those guys, for sure, and you’re just getting started. I don’t even know you understand yet how good you can be, and that’s the scariest part. You know what I mean? Just keep that mindset, keep doing what you’re doing. You know we’re locked in forever. So keep doing your thing, bro. You need me, hit me at any time. It goes vice versa.”

We're locked in forever.

You need me, hit me at any time.

That's the kind of player-speak that throws gas onto the fire of offseason speculation.

MORE: Chicago Bears' Breakout Defender Linked to AFC Squad Ahead of 2026 NFL Free Agency

Las Vegas Raiders defensive end Maxx Crosby (98) reacts during the second half.
Las Vegas Raiders defensive end Maxx Crosby (98) reacts during the second half. | Kiyoshi Mio-Imagn Images

To be clear, Crosby didn't say he wants to play for Chicago. He did not say he's requesting a trade. But when one of the NFL's elite pass rushers bonds with your franchise quarterback, it's going to generate serious buzz.

From a football standpoint, Crosby's fit with the Bears is obvious. Chicago already has Montez Sweat anchoring one side of the defensive line, and adding Crosby would create arguably the most disruptive pass-rush duo in the NFC.

For a team that took a massive leap in 2025 and is pushing for serious Super Bowl contention, trading for Crosby is the kind of move that screams "win now."

Crosby remains one of the NFL's most relentless edge defenders. He plays with a high motor, is a tone-setter, and is as productive as any pass-rusher in the league.

MORE: Chicago Bears Land Interior Force in Latest 2026 NFL Mock Draft

Pair that kind of defensive cornerstone with Williams, and the Super Bowl chatter will become deafening.

Indeed, trading for Crosby isn't as simple as just picking up the phone and agreeing to a deal. He has a massive contract and would cost the Chicago Bears a boatload of picks to acquire. Ryan Poles has historically shied away from that kind of move.

That said, moments like the one Williams and Crosby shared on the podcast do matter. Relationships can influence decisions. And if Crosby really does become available for trade, you can bet Williams will be in Poles' ear to get it done.

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Bryan Perez
BRYAN PEREZ

Bryan Perez founded and operated Bears Talk, a Chicago sports blog. Prior to that, he covered the Bears for USA Today’s Bears Wire and NBC Sports Chicago. In addition to his Chicago Bears coverage, Perez is a respected member of NFL Draft media and was a past winner of The Huddle's Mock Draft competition. Bryan's past life includes time as a Northeast scout for the CFL's Ottawa Redblacks.

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