The Chicago Bears already made a splash move ahead of the 2026 NFL Trade Deadline, trading for All-Pro defensive tackle Jeffery Simmons. But it doesn’t sound like General Manager Ryan Poles is closing up shop. The Nov. 10 deadline is approaching, and Chicago’s football team still figures to be in the thick of the trade action between now and when the clock strikes midnight.
Can Bears GM Ryan Poles Pull Off Two More Trades?
There is some fun Sunday reading to be had here in this piece by The Athletic’s Ted Nguyen, who has 10 hypothetical NFL trade deadline deals that could swing the race to Super Bowl glory. Among them are two trades involving the Bears:
Khalil Mack to the Bears for a fifth-round pick. Here’s what Nguyen had to say about this possibility:“The Mack and Bears reunion seems inevitable. The Chargers should be selling, and in the twilight of his career, Mack deserves to play with a contender. The 35-year-old is still playing at a high level as a run defender and pocket pusher. The Bears could use an ace at edge, but no one is just trading those away at the deadline. Mack can upgrade a decent edge rotation with Austin Booker and Montez Sweat, who returns from suspension this week. Maybe Mack has enough to have a signature postseason game and remind us all he’s a future hall-of-famer.”
I sure hope that feeling of inevitability translates into a trade actually happening.
If the Bears were able to successfully land the plane on a Mack trade, just know it’s not like they’d need him to be his 2018 self. Instead, what this team needs is someone who presents a clear upgrade and plays at a high level with more consistency than Austin Booker. This isn’t to say that Booker wouldn’t have a role on the Bears if they traded for Mack. But the team could better deploy Booker by being able to choose his spots.
Chicago Bears outside linebacker Khalil Mack (52) sacks Green Bay Packers quarterback Aaron Rodgers (12) in the first quarter at Soldier Field on Sunday, December 16, 2018 in Chicago, Illinois. Adam Wesley/USA TODAY NETWORK Riq Woolen to the Bears for a sixth-round pick. More from Nguyen:“Woolen signed just a one-year deal, and a team trading for him would only be on the hook for less than $1 million. Dennis Allen wants to play man, but he doesn’t have the corners to do so at a high rate. Jaylon Johnson and the Bears’ cornerback room are struggling this season. Woolen, 27, is an imperfect player, but his upside is huge, and his floor isn’t much lower than what Chicago has had. Like the Bills, the Bears’ offense makes them contenders, but they need defensive help even if the defense is punching above its weight right now.”
If Woolen’s name sounds vaguely familiar, it might be because we highlighted him in our post on Eagles players who could make sense for the Bears if Philly becomes a seller at the 2026 NFL Trade Deadline. This is what we had to say about Woolen at the time:
Woolen is probably my favorite Bears fit in this bunch. A fifth-round pick (153rd overall) in the 2022 NFL Draft, the 6-foot-4-inch Woolen was a Pro Bowler as a rookie in 2022 and a Super Bowl champion with the Seahawks in 2025. He is Pro Football Focus’ 17th-highest-graded cornerback this season, has a history of being sticky in coverage, and has a reputation as a ballhawk (6 INTs as a rookie, 12 overall). Chicago’s history with tall corners (Pro Bowler Nahshon Wright was 6-4, too! … 2025 NFL Draft pick Zah Frazier was 6-3) makes me think Defensive Coordinator Dennis Allen might have a type. Woolen, 27, has an expiring deal, so a trade wouldn’t be a major commitment.
Chicago’s loss to Green Bay in Week 5 exposed what could be a fatal flaw for the 2026 Bears. While rookies Dillon Thieneman and Malik Muhammad have upgraded the team’s speed in the secondary, there is still work to be done to build out the defensive backfield. Simply put, this team needs more speed and sticky coverage at cornerback. This is where someone like Woolen could fit.
Is Jaylon Johnson on the Trade Block?
NFL insider Tom Pelissero’s newsletter is a must-read every week. Not only is Pelissero on point when it comes to the Bears (remember, he broke the news of Jeffery Simmons’ trade to Chicago), but his coverage of league-wide matters is S-tier. So when I saw this mention of Bears cornerback Jaylon Johnson being a name possibly drawing interest in trade discussions, I did a double take.
More from Pelissero:
It’s unlikely the Bears will end up moving Johnson, who is in his seventh season in Chicago and sixth as a starter. But with Kyler Gordon making an impact since his return from injury and the team’s financial picture in flux after the Simmons trade, it would make sense to listen to calls. Johnson, 27, is due about $9.697 million for the rest of this season, including active roster bonuses, and $16 million in 2027 with no guarantees.
On the one hand, I can see where Pelissero is coming from in seeing a scenario in which Johnson is traded. Clearing some money off the books now (and next year) would serve the Bears well in the long run. But on the other hand, Chicago’s defense doesn’t have enough healthy corners to just give one away in a trade for the sake of creating cap space or adding draft capital. But I’m against it, as I’m open to any idea that makes the 2026 (and 2027 … and 2028) Bears better. But there needs to be a contingency plan to add another cornerback if Johnson goes.
Sep 20, 2026; Chicago, Illinois, USA; Chicago Bears cornerback Jaylon Johnson (1) runs onto the field before the game against the Minnesota Vikings at Soldier Field. Mandatory Credit: Matt Marton-Imagn ImagesEven though Pelissero says it is unlikely the Bears trade Johnson, it is still relevant that he has heard the cornerback’s name as someone who could be on the move. That said, perhaps that is where we can marry the two main storylines in this post. The Bears could trade Johnson, but only if they can swing a deal for a cornerback like Riq Woolen. Threading the needle here wouldn’t be easy, but the juice could be worth the squeeze if it means upgrading the secondary.
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