As the Super Bowl confetti settles and the champagne dries, the NFL shifts gears into its next high-stakes season: free agency. For some teams, it’s about finding that final puzzle piece.
For others, it’s a scramble to retain their stars before the bidding wars begin. The Cincinnati Bengals are firmly in the middle of that fray, and at the center of their offseason questions stands one of the league’s most disruptive edge rushers: Trey Hendrickson.
Hendrickson’s future in Cincinnati is anything but certain. Despite battling through injuries last season, his body of work over the past three years makes him one of the most coveted defensive players on the market.
He’s been a relentless force off the edge, ranking in the top five at his position in Pro Football Focus’ pass-rush grade on true pass sets (92.5). Just six edge rushers in the NFL have posted a pass-rush win rate above 20% over the last three seasons - Hendrickson is one of them.
That kind of production doesn’t go unnoticed, especially by teams desperate for pass-rush help. Enter the Chicago Bears.
According to PFF, Chicago profiles as a top landing spot should Hendrickson test free agency. The Bears finished 29th in pressure rate last season (31.1%), and while Montez Sweat gave them a spark with 10 sacks, the rest of the defensive line struggled to generate consistent heat.
Gervon Dexter was the next closest with six sacks, and beyond that, it was crickets. Adding Hendrickson to that front would instantly elevate Chicago’s ability to disrupt opposing quarterbacks - a missing ingredient in their defensive formula.
There’s also a familiar face in Chicago who could make the transition smoother: Dennis Allen. The Bears’ new defensive coordinator coached Hendrickson during his breakout years in New Orleans.
From 2017 to 2020, Allen helped mold Hendrickson into a double-digit sack threat, and the reunion could be appealing for both sides. Schematically, it’s a fit.
Personally, it’s a comfort zone.
But there’s a financial hurdle to clear. The Bears are currently projected to be about $5.3 million over the salary cap.
To make room for a player like Hendrickson - who’s expected to command north of $50 million at age 31 - Chicago would need to restructure deals or move off some big contracts. It’s doable, but it won’t be easy.
On the Bengals’ end, the writing may already be on the wall. Hendrickson’s relationship with the front office has been rocky in recent years, with trade requests and contract disputes dominating headlines in both 2024 and 2025.
Cincinnati’s front office has invested heavily in the edge position via the draft, using first-round picks on Myles Murphy and Shemar Stewart. With more talent like Rueben Bain Jr. and David Bailey waiting in the draft pipeline, the Bengals may feel they have the depth to move on.
But replacing Hendrickson’s production won’t be simple. He’s been one of the most consistently impactful defenders in the league when healthy. Even after a core muscle injury and surgery that sidelined him for much of the season, he remains the top edge rusher available in this year’s free agent class.
The Bengals are facing a tough decision. If they weren’t willing to extend Hendrickson when he was younger and healthier, it’s hard to imagine they’ll match what he’s likely to command now. And while fans in Cincinnati would love to see No. 91 back in stripes, the business side of the NFL may dictate otherwise.
If this is indeed the end of Trey Hendrickson’s run in Cincinnati, it was one to remember. He brought relentless energy, Pro Bowl-caliber production, and helped redefine the Bengals’ defensive identity during their recent playoff pushes.
His signing was one of the franchise’s best moves of the past decade. And while the story may be closing in the Queen City, it’s far from over for Hendrickson.
Whether it’s Chicago or another pass-rush-needy team, someone is going to pay him - and pay him well. The only question now is: who’s ready to make room for a game-wrecker?