Trey Hendrickson Linked to Bears Amid Bengals Contract Uncertainty

As Trey Hendrickson hits free agency amid contract uncertainty and injury setbacks, one analyst sees a surprise landing spot taking shape in Chicago.

Trey Hendrickson’s future in Cincinnati is anything but certain - and the league is watching closely. The veteran edge rusher, once a cornerstone of the Bengals' defensive front, is now at a crossroads. And while the focus often centers on what the Bengals will do, the reality is, other teams might end up dictating how this plays out.

Let’s start with the facts: Hendrickson is 31, coming off a season where he was limited to just seven games due to core muscle surgery. He managed four sacks in that span - a far cry from the dominant force who posted back-to-back 17.5-sack seasons and earned four straight Pro Bowl nods.

That dip in production, paired with the injury concerns, has cooled some of the heat around his name. But don’t mistake that for a lack of interest.

Hendrickson is still a proven pass rusher, and in a league where getting to the quarterback is gold, someone’s going to pick up the phone.

The Bengals gave him a one-year, $29 million deal last offseason. It was a bold move - a bet on his ability to stay elite.

But with Hendrickson now eyeing a multi-year contract with guaranteed money, the Bengals may hesitate to double down. They’re not in a position to throw big money at a player whose durability is now a question mark, especially as they juggle other roster decisions and a looming payday for Joe Burrow’s supporting cast.

So what are the options? A tag-and-trade is on the table, but that comes with its own set of complications.

Finding a trade partner for a 30-something pass rusher with a recent surgery and a hefty price tag isn’t exactly a layup. Front offices love production, but they also love flexibility - and Hendrickson’s next deal might not offer much of that.

Then again, if the Bengals simply let him walk, the market will tell us exactly how much value teams still see in him.

One team that’s already being linked to Hendrickson is Chicago. FOX Sports’ Greg Auman projects the Bears as a potential landing spot, and it makes sense.

Chicago’s defense took major strides last season, and adding a veteran edge rusher with Hendrickson’s pedigree could be the kind of move that accelerates their timeline. The Bears have cap space, a young core, and a head coach in Matt Eberflus who knows how to get the most out of his defensive front.

Hendrickson could be a natural fit.

But here's the catch: will anyone give him the kind of deal he’s looking for? ESPN currently ranks him as the No. 1 overall free agent, but that doesn’t guarantee a bidding war.

The likely scenario? Hendrickson lands a deal with incentives and maybe one year of guaranteed money - something in the ballpark of $20 million per year, but short on long-term security.

That could open the door for Cincinnati to sneak back into the picture if the market doesn’t materialize the way Hendrickson hopes.

It’s also worth noting: Hendrickson is sitting at 81 career sacks. He needs 19 more to hit the century mark - a milestone that’s well within reach over the next two healthy seasons.

That’s not just a stat; it’s a legacy number. And players chasing legacy often find an extra gear.

So here we are: Hendrickson wants security. The Bengals want flexibility.

And the rest of the league? They’ll decide what happens next.

Whether it’s Chicago or another team looking to add a proven pass rusher, Hendrickson’s next chapter is coming - and it could reshape a defensive front, just like he did in Cincinnati.