Bears win in Week 9 gives Chicago one last incentive to make an aggressive play before the deadline and bolster the defense

Will Ryan Poles make another mid-season trade before Tuesday’s deadline?

Kole Noble Chicago Bears News Writer
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Sep 21, 2025; Chicago, Illinois, USA; Chicago Bears head coach Ben Johnson on the sidelines during the first half against the Dallas Cowboys at Soldier Field.
Ben Johnson on the sidelines during the first half against the Dallas Cowboys at Soldier Field. David Banks-Imagn Images

The Chicago Bears got a huge win on Sunday against the Cincinnati Bengals, improving to 5-3 on the season and continue to prove there’s no apologizing for winning in the NFL.

At the same time, winning ugly isn’t sustainable and the Bears have some clear weaknesses on the roster that continue to get exposed on a weekly basis and will continue to be exploited down the road when the schedule gets even more difficult.

Ahead of Sunday’s game, NFL insider Jay Glazer reported Chicago as one of the teams who could be “aggressive” leading up to Tuesday’s trade deadline with a win. Chicago secured that win and now has even more incentive to make a last minute swing to improve the roster.

After the emergence of the run game with D’Andre Swift and Kyle Monangai since the bye week, running back should be off the wish list (for now). Instead, the priority needs to be on the defensive side of the ball after looking suspect again on Sunday, particularly at defensive end and cornerback.

Chicago had two new additions take the field in Week 9 at those two positions with defensive end Austin Booker making his regular season debut and newly-signed nickel C.J. Gardner-Johnson joining the squad. While both players played well on Sunday, it still wasn’t enough to hide the issues that have plagued the unit all season. So, let’s break down some of the top trade targets at both positions ranked from most likely to long-shot.

Breaking down potential Bears trade targets before Tuesday’s deadline

Most Likely

DE Matthew Judon: It’s not the prettiest option out there, but it’s realistic. I doubt the Bears want to use anything more than a Day 3 selection to make another addition to the roster and trading for Matt Judon makes a lot of sense. Ryan Poles previously attempted to land Judon but balked at the price when he was traded from New England. Now in Miami, Judon has been seldomly used and the Dolphins are in a position to have a fire sale after firing GM Chris Grier. A 6th/7th pick swap to bring Judon to Chicago would be the most likely option.

CB Alontae Taylor: At cornerback, I’m doubling-down on Alontae Taylor. Last Monday, I spoke with Adam Holt of A to Z Sports New Orleans to discuss this possibility. Taylor fits best in the slot, which is where the Bears signed Gardner-Johnson to play plus still have Kyler Gordon. But, when Dennis Allen was using him in New Orleans, Taylor played the majority of his snaps outside with mixed results. It’s worth checking the price and it’d be an easy transition back into a familiar scheme.

Possible

DE Jermaine Johnson II: The New York Jets are in an odd situation with new general manager Darren Mougey and head coach Aaron Glenn when it comes to building this roster. The two locked up multiple players over the summer and still have valuable players set to hit free agency that don’t seem to be in the team’s future. Jermaine Johnson II is one of those players. He’ll cost a lot more than Judon (Dianna Russini noted has high as a second-rounder) but he’s young and could stick beyond 2025.

CB Rasul Douglas: Originally, I had Marshon Lattimore in this spot, but after the knee injury he suffered un Sunday night’s game, I switched it to Rasul Douglas. Another member of the Dolphins who could be available for a simple late-round pick swap and has starting experience on the outside.

Long Shots

DE Trey Hendrickson: The long-shot, but still reasonable, target at defensive end is Hendrickson. The Bengals star pass rusher has had some pretty public disagreements with the organization over the last few months and is playing out the 2025 season on a revised contract. Cincinnati would be smart to get something for him this week, but it’s hard to give up such a talent for a team wanting to try and right the ship this season. Handing the Bengals a sixth loss on Sunday raises the chances Hendrickson gets traded but it’d still be quite the swing for Chicago to try and work out.

CB Riq Woolen: When the Bears drafted Zah Frazier back in April, I compared him to Riq Woolen, another fifth-rounder from UTSA. Chicago shut Frazier down for the season due to a personal matter ahead of the regular season and with issues in the secondary, going after a similar player for the remainder of the season is logical. Seattle doesn’t seem eager to move Woolen, but could if an aggressive offer is there. Again, I would be strongly against Chicago making any aggressive offer.