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Could the Bears swing a trade for Trey Hendrickson?

May 14, 2025 by WGN 9

CHICAGO (WGN) — 2024 NFL sack leader Trey Hendrickson and the Cincinnati Bengals are worlds apart on a contract extension. With Hendrickson publicly saying he will not play for the Bengals under his current deal Tuesday, could the Chicago Bears swoop in and make a trade for the All-Pro defender?

The math required to make such a move work is difficult.

As of Tuesday, the Bears have approximately $6.8 million in total cap space, but their effective cap space, which accounts for their top 51 roster spots and projected rookie contracts, is only $174,000, according to OverTheCap.com.

Hendrickson is reportedly seeking an extension in the ballpark of $30-35 million per year that would likely come with a large portion of the deal being guaranteed.

Comparatively speaking, Cleveland Browns star defensive end Myles Garrett signed a four-year, $160 million contract extension with $123.5 million in guarantees back in March so, think of a deal a notch or two lower than that.


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Without even considering what Chicago would have to give up in a trade, the Bears would need to restructure the contracts of several players (DJ Moore, Montez Sweat and Tremaine Edmunds) to free up the money needed to meet Hendrickson’s salary demands.

This would be done by converting large portions of base salaries into signing bonuses and kicking the can down the line on cap hits to lessen the financial load in the short term.

Another less likely option for Chicago could be outright releasing Edmunds and other more costly short-term contracts, like D’Andre Swift and Cole Kmet, to generate the cap space (releasing all three would open up approximately $31 million). But that would also cause talent and depth concerns, alongside putting the Bears around $21 million over the cap after absorbing Hendrickson’s contract and accounting for rookie deals.

The team also has to weigh extending All-Pro guard Joe Thuney, who’s in the last year of a five-year, $80 million contract he signed with the Kansas City Chiefs ahead of the 2021 NFL season.

That’s just the list of short term hurdles Chicago would have to overcome.

In the long term, Hendrickson turns 31 in December, making him a high-risk investment given that most NFL players start to decline after their age-30 season.

Acquiring Hendrickson and paying him the deal he wants would also muddy team financials 2-3 years from now. If his cap hit were to be in the $30-35 million range from 2026-27, it would push the Bears into a projected $52 million cap deficit starting in 2026 when factoring in existing contracts and a possible Thuney extension.

A Hendrickson trade could also hamstring Chicago from negotiating extensions or free agent deals at other positions of need in the future. Think about the Braxton Jones conundrum at left tackle, or whether or not to keep around safeties Kevin Byard and Jaquan Brisker.

All that being said, there are several reasons why finding a way to get Hendrickson in a Bears uniform makes sense.

Hendrickson, who has 35 sacks over the past two seasons, would give Chicago that highly sought-after one-two punch on both ends of their defensive line between him and Montez Sweat.

He also has past experience under new defensive coordinator Dennis Allen. Hendrickson played four years in Allen’s system when the two were together with the New Orleans Saints from 2017-20. That level of familiarity could not only give Hendrickson the ability to hit the ground running, but also allow for him to be an extension of the coaching staff that helps other players get acclimated to Allen’s scheme.

It’s just highly unrealistic given how many hoops the Bears would have to jump through to make a trade and contract extension happen.

Filed Under: Bears

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