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Chicago Bears All-Pro trade target threatens hold out amid contract stall 2 Bengals Trey Hendrickson celebrates a sack – Credit: Kareem Elgazzar/The Enquirer / USA TODAY NETWORK via Imagn Images

Chicago Bears urged to swing blockbuster Trey Hendrickson trade by insider

Originally posted on ChiCitySports | By Dan Fappiano | Last updated May 14, 2025 1:00 PM ET

The Chicago Bears have gone all-in on revamping their roster for success ahead of Ben Johnson’s arrival. However, one area of clear need that remains in pass rusher.

Chicago already has Montez Sweat and Dayo Odeyingbo on their roster. The latter was signed to a three-year, $48 million contract in the offseason after back-to-back 17 quarterback hit campaigns with the Indianapolis Colts. The former is the clear leader of the Bears’ defense and team’s sack leader from 2024. For all the changes Chicago could make to their defensive line, any decision will be built around Sweat.

But behind the pairing comes a lot of unknowns. Names like Austin Booker, Dominique Robinson and Daniel Hardy have potential, but none of them are proven. Trey Hendrickson of the Cincinnati Bengals certainly is, and would form one of the scariest duos in the league across from Sweat. With Hendrickson’s name continuously being thrown in trade rumors, longtime Bears insider Marc Silverman thinks it’s time general manager Ryan Poles makes a call to the Bengals.

Go get him.#Bears https://t.co/OHASb2xGs9

— Silvy (@WaddleandSilvy) May 13, 2025

Why Chicago Bears are being linked to Trey Hendrickson

Chicago Bears All-Pro trade target threatens hold out amid contract stall 2 Bengals Trey Hendrickson celebrates a sack – Credit: Kareem Elgazzar/The Enquirer / USA TODAY NETWORK via Imagn Images

The Bengals side both Ja’Marr Chase and Tee Higgins to massive extensions during the offseason. However, that has left Hendrickson without a long-term plan. The pass rusher has voiced his displeasure to the media and made it very clear that he is seeking a new contract. On Tuesday, he went as far as to say he wouldn’t play without a new deal in place.

Chicago is being linked as a potential suitor because of their need for a pass rusher. But it’s important to note that a Hendrickson trade won’t be simple. For starters, the Bears and Bengals must agree to terms on a new deal. Then, Chicago must sign Hendrickson to a long-term contract. The latter might be even more difficult based on the Bears’ current cap situation. But if the Bengals and Hendrickson truly can’t work things out, and the Bears shuffle around their cap space, the All-Pro would undoubtedly bring back the Monsters of the Midway mentality back to the Windy City.

Hendrickson is on a stretch of four-straight Pro Bowl appearances. But in 2024, he was named an All-Pro for the first time in his career. The Bengals star led the NFL with 17.5 sacks – it was his second-straight year with 17.5 sacks – alongside 36 quarterback hits and two forced fumbles. Hendrickson earned an 88.1 grade from Pro Football Focus, ranking 8/211 edge rushers.

The Bears haven’t had a player get double digit sacks since Robert Quinn’s 18.5 in 2021. While Sweat led the team in 2024, that meant just 5.5. Adding Hendrickson not only gives Chicago a dangerous weapon off the edge, but it should make things easier for Sweat in terms of getting to the quarterback. Overall, the Bears would have one of the most feared pass rush units in the entire NFL.

There are still plenty of hurdles to cross before Hendrickson even sniffs Chicago. However, he is only growing angrier with the Bengals. If they’re forced to put him on the trade block, it wouldn’t be a shock to see the Bears get involved.