Trade Market: Trey Hendrickson could be the missing piece for the Bears

Joseph Maiorana - USA Today Sports

Dustin Riese · Senior Writer · Tuesday, October 07 2025

As we sit here and prepare for the Chicago Bears bye week, all of that takes a backseat as the Chicago Cubs are in the NLDS. Talk about the perfect time to have a bye week when it comes to the fans, as the focus will be on the Cubs, as opposed to competing with the Bears for viewership options.

Soon enough, the focus will shift back to Chicago as they look to build on their two-game winning streak and strive to improve from one game to the next. One way for Chicago to do that would be to get as healthy as possible coming out of the bye, and from all accounts, it does appear the Bears are trending in that direction, which is all you can ask for.

Another way the Bears could continue to improve and make a playoff push is to look into the trade market and make a blockbuster deal. We have seen Ryan Poles do that before, when he brought in Montez Sweat. However, apart from his eight-game run in 2023, things haven't gone as planned for Sweat since he signed his extension.

Sweat was brought in here to improve the pass rush, and with that not panning out the way both parties had hoped, the Bears are still in need of more pass-rushing help. That is where Trey Hendrickson comes into play, as a trade for him would signal the Bears are in it to win for the long haul. Hendrickson was a name that circulated throughout Chicago during the offseason as an ongoing contract saga left his future in doubt.

He eventually signed a one-year deal to remain in Cincinnati, but from all accounts, this season could be the end of his time with the Bengals. With Joe Burrow out for the year and a defense that continues to struggle, Hendrickson's time with the Bengals could end sooner rather than later, as he will be a name floated around at the deadline.

Should that happen, Chicago needs to do whatever it takes to acquire him, as he would be the missing piece to their defense. There is no question that when healthy, Hendrickson is one of the best pass rushers in the game, as he has the capability to give you 15-20 sacks per season. Even on a team where the defense is terrible and he is their only option, Hendrickson still finds a way to produce, which is a feat in itself.

If you add him to the Bears' defense, not only would that open things up for him, but it would also open things up for Sweat and others, as that alone could help Sweat get back to his old ways and become the player the Bears expected him to be. Had the Bengals traded Hendrickson this offseason, the return for him would've been massive, but with this being the final year of his contract, Cincinnati may be forced to get rid of him for next to nothing as opposed to losing him for nothing as a free agent.

That alone could play into the Bears' hands, as you could see Chicago give up a second-round pick and an additional mid-rounder for Hendrickson. Talk about a massive steal if that is all it takes to get the job done. Cincinnati does earn its rights, but knowing what lies ahead and the possibility of them losing him for nothing, Hendrickson has the leverage as the Bengals are put in a tough spot right now.

For a team in desperate need of pass-rushing help, this is a no-brainer and the easiest pitch you can make to a GM who wants to win. Not only would Hendrickson be the elite pass rusher this team has been lacking since Khalil Mack, but Hendrickson could be in a position to stay there long term, as the Bears have the financial gains to make that happen.

Coming off back-to-back huge seasons where he averaged 17.5 sacks per season, no question that adding him to the defense would turn them into a top-10 if not a top-five unit, and that alone is worth discussing. He is a four-time Pro Bowler, and his ability to get after the quarterback would give the defensive line the spark they have been missing.