Should the Bears Trade for Trey Hendrickson?

The Chicago Bears once again won the offseason… for the third year in a row.
They have significantly improved the talent on both sides of the ball and emphasized increasing the competition across the board.
While they added a few quality defensive linemen, they could have a unique opportunity to land one of the league’s premier pass-rushers in Trey Hendrickson.
The Bengals are historically one of the league’s cheapest organizations. They notoriously didn’t have an indoor training facility until midway through the 2022 season. They recently made headlines for not having injury guarantees baked into rookie contracts if they were to get hurt in training camp (unlike every other NFL team). They also routinely let their pending free agents walk in free agency, even when they would have been obvious resign candidates if employed by other franchises.

PHOTO: Sam Greene/The Enquirer/USA TODAY NETWORK/Imagn Images
Many expected them to treat Tee Higgins with the same disregard they had for many Bengals of days past. Still, they surprised the masses when they resigned him to a four-year, $115 million deal just hours after inking Ja’Marr Chase to a four-year, $161 million contract ahead of free agency. Contrary to some of the opinions I’ve heard around social media (some people thought they should’ve let Higgins walk), those moves were smart and instilled hope that the team could be turning a new leaf. Unfortunately, Trey Hendrickson threw a bucket of water on that notion when he requested a trade after feeling disrespected by the lack of movement on his contract.
I know some think the fact that they signed Higgins and Chase limits their ability to resign Hendrickson, but that’s not the case. The Bengals have nearly $70 million in projected cap space next year. They could easily sign him to a two-year extension that locks him in through his age-33 season.
Hendrickson is now on the wrong side of 30 but has shown no signs of slowing down over the past couple of years.
In fact, he is coming off back-to-back 17.5 seasons and nabbed the first All-Pro nod of his career last year. He’s heating up at the right time and clearly knows it. An elite player playing out their contract year despite coming off their two best seasons is virtually unheard of. The four-time Pro Bowler recently vowed that he had no intentions of being a trendsetter in that regard, as he promised to hold out if the two sides don’t get a deal done.
Hendrickson’s recent discontent has put the Bengals in a precarious situation. They definitely hope he will cave, as their current pass rush leaves an awful lot to be desired without him in the lineup. However, the odds of his putting pen to paper there appear slim. The more important question for the sake of this article, though (my apologies for burying the lead; I felt this one needed to be fleshed out a bit more), is, should the Bears be interested? I ultimately believe that the answer to that question can be found by breaking it down to the two most important factors regarding the situation.
How Much Would He Cost?
Probably not that much at this point, honestly. The Bengals were rumored to be looking for a first-round selection and some extra draft capital to land him ahead of the draft. That’s an easy pass from the Bears’ perspective. However, that was before he promised to hold out if a deal didn’t get done ahead of the season. It was before he vented his frustrations to the press. We have reached a point where the asking price could lower by the day.
Could a team land him with a second and fifth-round selection? Maybe even a single second-round pick if the holdout bleeds into the regular season? I know fans are opposed to trading future capital, but it’s hard to say no to that deal if that’s all it would take to land the NFL’s reigning sack king.
Would the Bears Be Able to Re-sign Him?
That’s the catch. This question became more difficult to answer after the team re-signed Joe Thuney to a two-year extension. They may be willing to give up a second-round pick to land him, but there’s no point if they aren’t willing to pay him. I’m also sure Hendrickson would want confirmation that negotiations would resume before he steps on the field for whichever team trades for him.
While you certainly don’t like having your back against the wall when it comes to available cap room (which is how they were able to pry Thuney away from the Chiefs in the first place), they would be able to make it work as far as the cap goes. He is the perfect example of the type of veteran you go after when you have a quarterback on a rookie deal.
I’m generally not an advocate for predicting cost-cutting measures a year ahead, since there is no telling how the team will perform under new offensive and defensive schemes. D’Andre Swift could have a career year with Ben Johnson calling the shots. If he struggles, however, they would save $7.5 million by cutting him next year. They’d also save $15 million by cutting Tremaine Edmunds. I love Cole Kmet, but they just drafted a tight end in the first round. If Loveland makes 85 expendable as quickly as some expect him to, they could also save roughly $8.5 million by showing him the door this time next year.
On top of those potential cap casualties and trade candidates, I also need to mention that the cap is going up yearly. More importantly, it is also fake. Front offices have mastered the art of manipulating the cap. Even with the massive spending spree Chicago went on this offseason, they can pull off a big move if they want to dance with the cap devil.
If the price is right, it’s hard to say no to the prospects of landing someone of Hendrickson’s caliber.
However, they shouldn’t even consider the move if they don’t know that they can lock him in for the next couple of seasons.
If they have a plan to work around the cap, he would be well worth the price of admission it would probably take to land his services.
I’m not saying he would provide a Khalil Mack-level impact, but he would be the final piece to a Championship-level defense.
PHOTO: Sam Greene/The Enquirer/USA TODAY NETWORK/Imagn Images
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