Why The Chicago Bears Should NOT Sign Trey Hendrickson

I get it. The Chicago Bears are under the gun to make use of Caleb Williams’ rookie contract before they have to pay him $60 million a year for the rest of his life, which means they need to max out their roster as much as possible until he’s ready to carry the team himself. 

With that in mind, the Bears have a number of major moves to make in the 2026 offseason—both to shed necessary dead weight from their salary and to bring in players that will help them win a championship in 2025.

Chief among them in many Bears fans’ (and Pro Football Focus’) eyes is edge rusher Trey Hendrickson, who will soon become an unrestricted free agent after several highly productive years with the Cincinnati Bengals. 

Going back to his first year with the Bengals in 2021, Hendrickson has been one of the very best pass rushers in the NFL, twice reaching 20 or more sacks, having a pass-rush grade of 86 or better, and consistently being among the top-10 players in win percentage on true pass-rushes. As such, it might seem like a no-brainer to go all-in on the pass rush with Hendrickson on one side and Montez Sweat, who has struggled at times without an elite pass-rusher opposite him.

But free agency isn’t about rewarding what a player has done. It’s about what they’re going to do. Which is why I think the Bears should steer clear of Hendrickson for this extremely important time in their development as a consistent power in the NFC.

Last year, unfortunately, was a harbinger of what might await the 31-year-old Hendrickson going forward: a drop-off in production due to injury (only four sacks and 23 pressures in eight games). It also saw Hendrickson’s production in true pass-rush situations dip, though he was still in the top-15 in win rate.

The problem is that Hendrickson, after making $30 million last season, will no doubt be looking for three-plus-year deal for at least that amount, which is the going minimum for top-flight pass rushers these days. The Bears simply don’t have the money to do that, with Sweat still having two years remaining on his deal and Chicago having no reliable way to get out from Dayo Odeyingbo’s three-year, $48 million deal while he recovers from an Achilles injury. And, just in case some of you are considering it, swapping Sweat out for Hendrickson still doesn’t completely solve Chicago’s problem of needing more production from players like Austin Booker or being unable to stop the run on the interior.

If I were the Bears, I would be more willing to potentially send draft capital to the Las Vegas Raiders to get them to try to take on a bit more of Maxx Crosby’s contract than give the same money to Hendrickson, who’s three years older, coming off a down year, and not quite as game-changing as the Raiders star. Because Crosby, much like the Packers’ trade for Micah Parsons last year, makes the Bears an instant Super Bowl-caliber defense. Signing Hendrickson makes them better, but not to the same degree. If you’re going to swing for it, go all the way, right? And if they can't go all the way in on Crosby, I'd almost rather try to see what Booker can do and see if the Lions would dare part with Alim McNeill, which would solve the Bears' arguably bigger defensive problem at tackle. (Fat chance, but why not ask?)

Personally, I think the Bears are in a tough spot as far as getting elite difference-making talent at edge in this year’s draft, despite it being a deep class with intriguing prospects. They simply performed a bit too well this year to get a blue-chip prospect at that position, and they have other needs at defensive tackle and potentially left tackle they need to address now, as well. That suggests they probably have to sign or trade for an edge to make their defense more dangerous in 2026.

But that doesn’t mean Hendrickson, a really good player who’s unfortunately just a little too far down the road in his career, is the right investment at this stage.