Bear Digest

Chicago Bears Dubbed 'Team to Keep an Eye On' for Top Free-Agent Pass Rusher

ESPN linked the Bears to one of the top defenders in 2026 NFL Free agency.
Bryan Perez|
A general view of a Chicago Bears helmet
A general view of a Chicago Bears helmet | Denny Medley-Imagn Images

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Chicago Bears

When ESPN assessed the 2026 NFL free agency landscape, one line stood out for Chicago Bears fans when Matt Bowen predicted the best fit for Cincinnati Bengals superstar edge rusher Trey Hendrickson:

"The Bears are a team to keep an eye on here, too."

The reasoning is obvious. Hendrickson is one of the most proven pass rushers scheduled to hit the open market. It's rare for a player with his resume to become available. For a team like the Bears, which must upgrade their pass rush, connecting Hendrickson to Chicago is an easy line to draw.

MORE: Chicago Bears Land Interior Force in Latest 2026 NFL Mock Draft

Although Hendrickson's 2025 season was limited to seven games because of injury, he still posted four sacks. In 2024, he led the NFL with 17.5.

ESPN suggested the most logical landing spot for Hendrickson is the Indianapolis Colts, but calling the Bears a "team to keep an eye on" signals that Chicago is expected to be aggressive with the top-of-the-market pass rushers.

Cincinnati Bengals defensive end Trey Hendrickson (91) celebrates the win.
Cincinnati Bengals defensive end Trey Hendrickson (91) celebrates the win. | Joseph Maiorana-Imagn Images

According to current free-agency projections, Trey Hendrickson's market value could be in the $25-$30 million per year range. Whether or not Bears GM Ryan Poles is willing to commit that kind of payday to a 31-year-old pass rusher remains to be seen.

MORE: Chicago Bears' Breakout Defender Linked to AFC Squad Ahead of 2026 NFL Free Agency

Still, beggars can't be choosers. The Chicago Bears struggled to consistently generate pressure beyond Montez Sweat. Adding a past sack champion to the roster would not only bring legitimacy to the Bears' pass rush but also cause opposing offensive coordinators to pick their poison. The days of focusing O-line protections on Sweat would be over.

If Poles is going to take a big swing on a player like Hendrickson, he could be in a now-or-never window. Caleb Williams is still on his rookie contract, but he'll be extension-eligible at the end of 2026. Once QB1 inks his expected massive second deal, luxury signings like Hendrickson will be much harder to pull off.

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Bryan Perez
BRYAN PEREZ

Bryan Perez founded and operated Bears Talk, a Chicago sports blog. Prior to that, he covered the Bears for USA Today’s Bears Wire and NBC Sports Chicago. In addition to his Chicago Bears coverage, Perez is a respected member of NFL Draft media and was a past winner of The Huddle's Mock Draft competition. Bryan's past life includes time as a Northeast scout for the CFL's Ottawa Redblacks.

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