Bear Digest

Potential trades the Bears could make for Trey Hendrickson

With the Cincinnati Bengals officially listening to trade offers for star pass rusher Trey Hendrickson, the Chicago Bears have multiple ways to make a deal.
Pete Martuneac|
Sam Greene/The Enquirer / USA TODAY NETWORK via Imagn Images

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Navigating one contentious contract negotiation is bad enough for an NFL team, but the Cincinnati Bengals have had to work through two this offseason, and both at the same position. Rookie defensive end Shemar Stewart and the Bengals eventually hammered home a workable deal, but the NFL's reigning sack leader Trey Hendrickson remains a holdout (technically a hold-in now that he's reported to training camp but still won't practice).

Apparently, negotiations between Hendrickson and the Bengals have reached a breaking point and the team is now officially listening to trade offers, per NFL insider Ian Rapoport.

Just about every team in the league should be interested in acquiring a pass rusher of Hendrickson's caliber, including the Chicago Bears. If they finally got the head coach and quarterback right, and all signs indicate that they have, then this is the time to go all-in on a Super Bowl run.

It'd be tough to get a deal done and also pay Hendrickson the money he's seeking, but here are four potential trades the Bears could make to bring him into Halas Hall.

1. Montez Sweat and a 2026 fifth-round pick

The biggest obstacle stopping Chicago from bringing in Hendrickson is paying him what he wants. The Bears are right against the salary cap for the first time in years and have young players that may earn huge contracts in the coming two years. The easiest solution would be to include Montez Sweat in a trade with the Bengals plus a future pick.

Sweat signed a four-year, $98 million contract with the Bears shortly after they acquired him in a trade at the 2023 deadline. Hendrickson would likely earn more than this, but by moving Sweat and sending his salary along with him, it would be easier to pay Hendrickson. The only drawback would be the diminished return of Hendrickson. While he would certainly be an upgrade over Sweat, Chicago would still be without a reliable second pass rusher.

2. Tremaine Edmunds and a 2026 fourth-round pick

Similar to the Sweat deal, the Bears would be able to offload a pricey contract to make more room for Hendrickson against the salary cap, though this path has the added benefit of keeping Sweat. Chicago would feature one of the league's most fearsome pass rush duos, but its linebacker corps would be diminished. Edmunds may have been slightly underwhelming last year, but new defensive coordinator Dennis Allen believes he can unleash the beast in Edmunds.

3. Chicago's 2026 second-round pick

When the Bengals first gave Hendrickson permission to seek a trade, Jonathan Jones of CBS Sports speculated that, considering the immense contract that Hendrickson's new team would be expected to sign, the trade compensation would likely be in the range of a high third-round pick or a low second-rounder.

If the Bears want to add Hendrickson without reducing their roster elsewhere, then they'd have to cough up valuable pick, probably second-rounder. If all went according to plan, that pick would be near the back of the second-round, anyway, making the deal easier to swallow.

The contract is where things could get sticky. The Bears have just $13 million in cap space available according to Over The Cap, and not a whole lot of ways to expand that. Luckily for the Bears, a shrewd NFL general manager has many tools at his disposal to create salary cap space, and GM Ryan Poles could probably figure it out, though it may be costly in the long run.

Trey Hendrickso
Sam Greene/The Enquirer / USA TODAY NETWORK via Imagn Images

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Pete Martuneac
PETE MARTUNEAC

A former Marine and Purdue Boilermaker, Pete has been covering the Chicago Bears since 2022 as a senior contributor on BearsTalk. He lives with his wife, two kids and loyal dog.

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