The Bears already made the kind of move that changes the entire conversation around a trade deadline.
Chicago shocked the league by landing All-Pro defensive tackle Jeffery Simmons from the Titans, a deal that instantly shifted the spotlight onto Ryan Poles and whatever he might still have up his sleeve. Simmons leaves Tennessee and joins a Bears team trying to keep pushing forward, while the Titans continue toward the No. 1 overall pick in next year’s draft, a spot they know well in recent years.
With that blockbuster out of the way, the bigger question is what Chicago can still do. The answer starts with the draft capital the Bears still control after the Simmons deal.
For 2027, Chicago still has a second-round pick, a third-round pick, a fifth-rounder via Atlanta, a sixth, and a seventh. In 2028, the Bears still hold a second, third, fourth, fifth, fifth via Tennessee, sixth, and seventh.
But after giving up two first-round picks, the Bears are almost certainly done dealing premium capital. Any further move is expected to be built around Day 3 picks. A second- or third-rounder feels highly unlikely now, and even a fourth-rounder would be a surprise after the Simmons trade.
That leaves Chicago looking at a narrower class of targets, and the biggest name still floating around is a familiar one: Khalil Mack.
Mack, EDGE, Chargers
Mack has been quiet since opening the season with 3.0 sacks in his first four games, but the Chargers’ situation keeps getting worse. He’s on a one-year contract, which makes a reunion with the Bears easy to understand. Chicago has generated sacks at a better rate than expected this season, but it still doesn’t look quite complete enough on that side of the ball to chase a championship.
Donte Jackson, CB, Chargers
Cornerback remains the most obvious weakness on the roster. Between Jaylon Johnson and Tyrique Stevenson, the Bears do not have a dependable starting answer next to rookie Malik Muhammad.
Jackson is one of the Chargers players who could be moved, and before a hamstring injury he had allowed an opposing quarterback rating of 89.6 through four games.
Nahshon Wright, CB, Jets
This one fits neatly. The Jets have not used Wright, and he has grown more frustrated with his role in New York.
Bears fans already know what he can do. Last season, he produced five interceptions and three fumble recoveries. He would make sense as a late Day 3 addition for a player who already knows Dennis Allen’s defense and could push Johnson and Stevenson.
Shemar Stewart, EDGE, Bengals
This is the odd one in the group. Stewart was a first-round pick in 2025, but he is not being used in Cincinnati. That alone raises the possibility that he could be available.
The bigger question is price. Would the Bengals really expect premium compensation for a player they drafted just last year? Based on how they’ve handled him so far, that seems hard to believe.
Riq Woolen, CB, Eagles
Woolen is the kind of player who comes with plenty of volatility. He can be a problem at times, but he also brings size and speed that stand out immediately.
He’s not perfect, and he’s had his rough moments this season. Still, he looks like a better option than Johnson or Stevenson, which is why he belongs in the conversation. The Bears need help at corner, and Woolen offers a higher ceiling than what they’re currently working with.
The chatter around Mack isn’t slowing down either. Ted Nguyen of The Athletic said Sunday that a Mack-to-Chicago reunion “seems inevitable,” and there have been multiple reports suggesting the cost could be as low as a fifth-round pick for the Bears.
There’s also been noise around Woolen. Nguyen’s Sunday morning report included a deal in which Chicago would send a sixth-round pick to land the corner.
As for Mack, Sports Illustrated’s Albert Breer reported that the Chargers have “shut down” trade offers so far. But with the Chargers now 0-7 and Mack on a one-year deal, that kind of stance may not hold for long.
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Jeffery Simmons wasted no time making his presence felt in his Bears debut, giving the front seven a jolt that showed up all over the field. Caleb Williams, Luther Burden III, Montez Sweat, Rome Odunze and DAndre Swift also turned in notable performances, and the bigger takeaway for Chicago is that these wins no longer feel like isolated bursts. They are starting to look like evidence that this team may actually be building something real. [Read more 🡒]