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Syndication: The Enquirer Trey Hendrickson celebrates a defensive stop – Credit: Albert Cesare / The Enquirer / USA TODAY NETWORK via Imagn Images

Chicago Bears’ Trey Hendrickson trade plans doused in cold water by insider

Originally posted on ChiCitySports | By Dan Fappiano | Last updated May 14, 2025 3:00 PM ET

With All-Pro pass rusher Trey Hendrickson expressing his displeasure with the Cincinnati Bengals, the Chicago Bears have been linked as a potential trade partner. However, general manager Ryan Poles actually pulling off a trade for Hendrickson comes with numerous hurdles.

The whole reason Hendrickson has come up in trade rumors is due to his contract. Set to be a free agent after the season, he has seen both Ja’Marr Chase and Tee Higgins sign massive extension. Without a new deal in place, Hendrickson has said he won’t play in 2025. The Bengals would seemingly want to recoup draft capital for the All-Pro rather than have him sit out and eventually walk in free agency.

But for as tantalizing as Hendrickson in the Windy City may be, Brad Biggs of the Chicago Tribune doesn’t see it coming to fruition. Poles can always pull off a shocker and send the Bears’ defense into overdrive. Still, he must consider what it would cost to retain Hendrickson and the pieces Chicago already has on their defense.

“I don’t see how it makes sense to trade 2026 draft capital for Hendrickson, pay him a contract that likely would exceed $30 million per season and then use Odeyingbo as a part-time role player behind Sweat and Hendrickson with an average annual salary of $16 million,” Biggs wrote. “That just doesn’t add up to me.”

“I’d add that any team acquiring Hendrickson likely would view him as the final piece to a championship run. That’s how I’d look at him, anyway, if I were considering trading for him,” he continued. “The Bears are in Year 1 for coach Ben Johnson and coming off a five-win season. They’ve made some interesting moves this offseason and no doubt strengthened the roster. ”

“They have roughly $7.5 million in available cap space, which ranks 28th in the league, according to Spotrac.com,” Biggs concluded. “Yes, they easily could move money around in some veteran contracts to create more space, but do that and all of a sudden they go from being a team with a lot of cap flexibility to one that is tighter.”

Chicago Bears, Trey Hendrickson trade problems

Syndication: The Enquirer Trey Hendrickson celebrates a defensive stop – Credit: Albert Cesare / The Enquirer / USA TODAY NETWORK via Imagn Images

For starters, the Bears and Bengals must come to terms on a deal. As Biggs points out, Cincinnati requesting a first-round pick would likely end conversations. Even a second or third-rounder is premium capital to give up. And while Hendrickson is an elite player, Chicago is still building their foundation under new head coach Ben Johnson.

The bigger problem, though, is signing Hendrickson to a contract extension. Coming off of four straight Pro Bowl appearances and his first All-Pro season, the pass rusher is expecting to be paid handsomely. While Hendrickson deserves the new contract, the Bears already gave fellow edge rusher Dayo Odeyingbo a three-year, $48 million contract. With Montez Sweat and his $98 million contract also on the books, Chicago would be dedicating a massive part of their cap space to the position.

Of course, until a Hendrickson conclusion is made, Bears fans will continue to clamor for a trade. It’s not hard to see how exciting the pairing of Sweat and Hendrickson would be. The Bengals star is coming off of back-to-back 17.5 sack campaigns, racking up 61 quarterback hits in that span. The Bears haven’t had a double-digit sack campaign since Robert Quinn’s 18.5 in 2021. Hendrickson would singlehandedly end that streak.

Biggs points to the Cleveland Browns and how they handled their seemingly unwinnable situation with Myles Garrett. Maybe the Bengals do the same with Hendrickson. But even if the pass rusher ends up on the trade block, it’d be a bit of a shock to see him land in the Windy City.