The Chicago Bears are entering a pivotal stretch in their offseason-one that could shape the next phase of their rebuild. With the Senior Bowl now in the rearview mirror, GM Ryan Poles and new head coach Ben Johnson are shifting gears from scouting college talent to evaluating their current roster.
The priority right now? Deciding which players to retain before free agency opens next month and which ones they’ll have to let walk.
But while the front office is still weighing internal decisions, defensive coordinator Dennis Allen already has his eyes on a familiar face: Trey Hendrickson.
Sources inside Halas Hall say Allen is pushing hard for Poles to make a run at the veteran edge rusher. It’s not just wishful thinking-this connection runs deep.
Allen was instrumental in Hendrickson’s early NFL development back in New Orleans, where the Saints drafted him in the third round. Despite Hendrickson’s promise, the Saints’ depth at defensive end-featuring Cameron Jordan and former first-round pick Marcus Davenport-meant there wasn’t room to keep him long-term.
He eventually landed in Cincinnati, where he blossomed into one of the league’s most disruptive pass rushers.
Even at 31, Hendrickson has shown he’s still got juice. His 2025 campaign was cut short due to injury, but in just seven games, he racked up four sacks and eight quarterback hits. That’s still impact production, and assuming he's fully healthy by training camp in July, he could be a major asset for a Bears defense that’s looking to take another step forward.
Pairing Hendrickson with Montez Sweat and promising young pass rusher Austin Booker could give Chicago the kind of edge rotation that keeps offensive coordinators up at night. It’s the kind of move that could unlock the full potential of Allen’s defensive scheme-generating pressure with the front four and allowing more flexibility on the back end. And if the Bears can solidify their edge group with a proven vet like Hendrickson, it frees up Poles to focus on other areas of need in the draft, like defensive tackle, linebacker, and safety.
But here’s the catch: money.
Hendrickson isn’t going to come cheap. Cap analysts project his next deal to be in the ballpark of $25 million per year.
With his 32nd birthday coming up in December, he’s likely looking for a short-term deal-maybe two years-but with premium pay. That’s a tough ask for a Bears team currently sitting about $10 million over the cap.
If Chicago wants to make this work, it’s going to take some creative accounting. Restructures, cuts, and cap gymnastics will all be on the table.
The question is: how badly does Allen want him, and how far is Poles willing to go to make it happen?
There’s also the wild card of the open market. Edge rushers are always in demand, and Hendrickson’s résumé-double-digit sack seasons, playoff experience, and a motor that hasn’t quit-makes him one of the more attractive options out there. If a bidding war breaks out, the Bears may have to bow out.
But don’t rule out the power of familiarity. Hendrickson could be intrigued by the idea of reuniting with Allen, the coach who helped mold him into a pro. And after watching the Bears make a deep playoff run this past season, he may see Chicago as a team on the rise-and a place where he could make a real impact.
It’s early in the offseason, but this is one storyline worth watching. If Allen gets his guy, the Bears’ front seven could look a whole lot scarier in 2026.