The Chicago Bears swung for the fences when they acquired four-time Pro Bowl defensive tackle Jeffery Simmons in a blockbuster trade this week, but he might not be their last big-name addition before the NFL trade deadline arrives in 11 days.
In an NFL-shaking move, the Bears acquired Simmons and a 2027 fifth-round selection from the Tennessee Titans in exchange for their next two first-round picks and a 2027 fourth-rounder, processing the blockbuster trade late on Thursday, October 29.
The massive move marked a significant investment for the Bears, who not only gave up their top picks in the next two years but also took Simmons’ massive contract — which, starting in 2027, will carry an average annual value of $35 million through 2029.
According to ESPN’s Ian Rapoport, though, the Bears might still have their eyes on a reunion with All-Pro pass rusher Khalil Mack before the November 10 trade deadline.
“Khalil Mack is another big-time name that we are going to be discussing before the trade deadline,” Rapoport said Thursday on NFL Network after the Simmons trade. The Los Angeles Chargers have yet to win a game. They do not believe they are in sell mode. They believe they are going to turn it around.
“At some point, if they do not turn it around, Mack will be the top name. The Chicago Bears just traded for Jeff Simmons. They still do have a need on the edge. I would expect them to at least inquire about [Mack].”
Bears Could Technically Afford Trade for Khalil Mack
The suggestion that the Bears could trade for Simmons and Mack before the trade deadline with less than $10 million in cap space sounds like a fantasy out of Madden, but Rapoport’s hint that they could circle back to Mack has basis in reality.
For starters, the Bears took on a major expense when they acquired Simmons, but the big money doesn’t kick in until next season. They will owe him only about $7.9 million for the rest of the 2026 season, which leaves them with about $1.26 million in space.
Meanwhile, Mack will cost even less if another team acquires him. The Bears would only be on the hook for the rest of Mack’s $8 million base salary if they traded for him, and that number — which is now about $4.44 million — only gets lower with each passing week.
The Bears would still need to make a few adjustments to clear cap space for Mack — even if they wait until his remaining salary drops to just $4 million after Week 9’s games — but they have more than a few restructure options to make it work.
Bears News: Ryan Poles Casts Doubt on Another Big Trade
Rapoport expects that Chicago will check in again on Mack before the trade deadline, but Bears general manager Ryan Poles sounded far more apprehensive about making another big move after paying so much to acquire Simmons.
“We gotta be very smart how we move forward when you make a deal like that,” Poles told reporters on Friday, October 30. “I don’t think we’re gonna throw picks all over the place right now. We’re gonna be smart about it. Obviously, we’re gonna listen and see if something makes sense or not. I’d like to think the whole process will slow down just a little bit.”
Even if the Bears do call about Mack, the Chargers don’t seem open for business.
NFL insider Albert Breer noted that while teams have called the Chargers about Mack and other targets, the Chargers have not engaged and appear “unwilling to waive any sort of white flag.”
Things can change — especially if the Chargers move to 0-8 before the deadline — but it is just as likely that the Bears move on from that line of thinking and find a more manageable target.
Bears Eyeing Deal for All-Pro Pass Rusher After Jeffery Simmons Trade