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After the confetti falls and the winners hoist the Super Bowl trophy, an entirely new battle will begin, one that focuses on free agency. Some teams will be looking for the missing piece while others try their best to hang onto their best players. Money will be flying all over the place and the signing alerts will soon be blowing up a phone near you.
The Bengals will be no different especially as it pertains to star pass rusher Trey Hendrickson. Recently Pro Football Focus slotted the Chicago Bears as the best fit for the defensive end, should he choose to test the lucrative waters of the free agency pool. They noted the Bears’ lack of quality pass rush, as they finished just 29th in pressure rate (31.1%) last year. Hendrickson may have been limited by injury last year but over his last three years he has been one of the more dominant forces on the edge. He ranks in the top five at his position in PFF pass-rush grade on true pass sets (92.5) and stands as one of just six edge rushers with a pass-rush win rate above 20% over his last three seasons. Montez Sweat still managed to wrack up ten sacks for Chicago, but the next highest total was 6 by Gervon Dexter. They were in the bottom third of the league in pressures and apart from Sweat the defensive line failed to get to it the quarterback in any real way. Adding Trey Hendrickson to that lineup in the Windy City might be exactly what they need to push even farther towards a championship.
Signing with Chicago would make logical sense as it would mean a reunion between Hendrickson and former coach Dennis Allen, who is now the Bears defensive coordinator. Hendrickson first exploded into a double-digit sack threat under Allen’s guidance in New Orleans. During his four-season stint with the Saints (2017–2020), he recorded a total of 20 sacks for Allen before leaving for Cincinnati in free agency.
And perhaps the time is right for a change of scenery for him. Fans well know the tortured his story of his demands for trades in 2024 and 2025 and his contractual disputes and “hold ins” that so often dominated offseason discourse. Hendrickson is expected to fetch a contract of over $50 million at age 31 which is something the Bengals may be hesitant to try to match even if he is interested in a Queen City reunion. A complicating factor here is that the Bears are currently estimated to be approximately $5.3 million over the cap. Without major restructuring of contracts and/or moving on from some of their more expensive players, freeing capital to pay what Hendrickson will be asking for would be financially very tricky.
Cincinnati’s ability (or willingness) to make a competitive offer would have to take into account the fact that the they have already spent enormous draft capital on the edge position, including two first round picks in Myles Murphy and Shemar Stewart. With even more defensive end talent potentially waiting in the wings in the NFL draft in the form of Rueben Bain Jr. and David Bailey, Cincinnati will likely have the players to try to replace Hendrickson if he does choose to walk. Though replicating his production is another question altogether.
The reality is that he is 31 and coming off a core muscle injury and surgery that cost him more than half a season. This isn’t to say that he won’t get a king’s ransom in the open market. He’s the top free agent of the entire 2026 crop as reported by multiple media outlets. But if the Bengals weren’t willing to pay Hendrickson top tier money when he was a year younger, and a year healthier, it’s highly unlikely that they will match the offers he’s likely to get from a team ready to make him their top shelf option rushing the passer.
As much as it may hurt to admit, it seems that we’ve likely seen Trey Hendrickson play his last snap for the Orange and Black. It was an amazing run full of pro bowl type performances and his acquisition was one of the best that Cincinnati has made in the past decade. It is a shame that money and contracts spoiled so much of his final games with the team, but the NFL is a business at the end of the day. And wherever he may end up, Trey Hendrickson will surely get the payday he and his agent feel he deserves. If Chicago can find the money, they sure have the desire and the need, and so it may well work out that way, though time will tell.
