The Chicago Bears have won four games in a row and sit two wins above .500 with two weeks remaining ahead of the NFL trade deadline.
Chicago (4-2) is entering a two-game road stretch in which the team visits the Baltimore Ravens and Cincinnati Bengals, respectively. That looked like a brutal double-header away from Soldier Field heading into the season, though it is far less daunting now.
The Ravens (1-5) are banged up across the roster and may not have quarterback Lamar Jackson at their disposal again this weekend. Meanwhile, the Bengals (3-4) are without quarterback Joe Burrow indefinitely and will rely on 40-year-old Joe Flacco for as long as he remains healthy.
As such, the Bears could find themselves with a record as good as 6-2 a mere 48 hours before the November 4 trade deadline arrives. So the question is whether Chicago should buy, sell or simply ride out the year with the roster as it is?
There are certainly areas in which the team could use a talent upgrade, with edge-rusher standing out clearly above the rest. The Bears have amassed just 12 sacks through six games, leaving them tied with the Arizona Cardinals for 25th in the league in that category, though it is fair to point out that some teams ahead of Chicago have played seven times already this season.
Cody Benjamin of CBS Sports recently listed the Bears as a top potential landing spot for defensive end and reigning NFL sack champion Trey Hendrickson of the Bengals.
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“Riding high off the spark of Joe Flacco’s emergency arrival, Cincinnati will probably be motivated to hold, not sell, as it awaits Joe Burrow’s late-year return,” Benjamin wrote. “Still, Hendrickson has struggled to get a firm long-term commitment from Bengals brass for years. And he’d look pretty good bringing his pure pass-rushing skills to, say, a team already positioned to make some late-year noise.”
Hendrickson is in the final season of his contract, which pays him $29 million. He will play the majority of the 2026 campaign at the age of 31 and will be looking for a long-term extension next offseason if Cincinnati does decide to deal him. Spotrac projects Hendrickson’s market value at just shy of $140 million total (approximately $35 million annually) over a new four-year deal.
The Bengals are also unlikely to let Hendrickson go for anything less than a second-round pick, and may need to lose their next two games against the New York Jets and Chicago to even consider such an agreement.
The Bears will eventually need to invest in the position, though paying that kind of money and draft capital for a player on the wrong side of 30 carries a meaningful risk/reward element.
That said, Hendrickson put up 17.5 sacks in 2024 and finished second in Defensive Player of the Year voting. He has tallied eight quarterback hits, four sacks, three tackles for loss, one forced fumble and one pass breakup in six games played this season.
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