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The Bears were linked to interest in Mack by FOX Sports' Jay Glazer a few weeks back, which makes sense because Chicago could use more depth at edge rusher.
Unfortunately for the Bears and their fans, it doesn't look like a reunion is likely.
The Chargers have said publicly they don't want to trade Mack, and Mack has said he doesn't want to be traded. Adding to that, reports suggest the Chargers and Mack aren't lying.
"Despite their 0-7 record, the Los Angeles Chargers continue to tell teams that they have no interest in trading away Khalil Mack, and the veteran pass rusher will not be going anywhere before Tuesday's deadline, according to sources," ESPN's Adam Schefter and Ian Rapoport reported.
There's a few reasons why we're holding out hope. One of them has to do with the fact that this could simply be posturing on the Chargers' part in order to try and get more for Mack.
It also makes no sense for both sides to stay together. Mack may very well be in the final year of his career after mulling retirement in the past and it's hard to fathom him staying with an 0-8 team going nowhere. The Chargers would be better served moving on and picking up a draft pick.
Trade chances: 20%
The Bears could use another starting-caliber player at cornerback given the struggles of Jaylon Johnson and Tyrique Stevenson this season. At the very least, more depth is needed.
Woolen is a great fit because he thrives in man coverage, which the Bears play at the second-highest rate in the NFL this season, and Woolen has plenty of starting and even playoff experience, and has been better than Johnson in 2026.
The Philadelphia Eagles showed they are ready to sell after trading Jordan Davis to the Jacksonville Jaguars, and it makes sense to deal Woolen, also, as he'll be a free agent in 2027.
Cost will be important here, but with Woolen's price likely being a fourth-round pick, at most, we could see the Bears making this trade.
Trade chances: 60%
Wright left for the New York Jets in free agency and that proved to be a colossal mistake for the veteran cornerback.
Wright has not played a single snap on defense this season and has routinely been a healthy scratch. Safe to say, Wright likely wouldn't mind getting out of there and Gang Green probably wouldn't be opposed to trading him, either.
Wright started in 16 games for the Bears last season and was pretty solid. He also proved to be a turnover matchine after notching five picks.
There wouldn't be much of an acclimation period, either, thanks to Wright's experience in Dennis Allen's defense. He will also be dirt cheap, which only adds to the likelihood the Bears will at least have interest in him.
Trade chances: 80%
After losing Cole Kmet to a season-ending injury, the Bears, who use a lot of 12 and 13 personnel, are relying heavily on rookie Sam Roush, who has struggled this season, and uninspiring veteran Stephen Carlson behind Colston Loveland.
The Bears could use a well-rounded tight end like Goedert, who has proven to be a solid blocker and very good pass-catcher during his career.
The rules for why the Eagles would trade Woolen apply for Goedert, although the latter obviously has a deeper connection with the Eagles because he has spent his entire career there.
At a reasonable price of a fourth- or fifth-round pick, it wouldn't shock us to see the Bears trade for Goedert, although we don't believe it's likely, either, since the Bears have bigger fish to fry.
Trade chances: 20%
Here's a more realistic option for the Bears at tight end.
Alie-Cox doesn't offer as much in the pass-catching department as Goedert, but he's serviceable in that area and is as good, if not better, as a blocker. Alie-Cox will come cheaper than Goedert, also, with it likely costing a sixth-round pick, at most.
The Indianapolis Colts are in the midst of a fire sale after trading off Quenton Nelson and DeForest Buckner, so everyone is on the table right now, and especially when it comes to players who are slated to be free agents like Alie-Cox is.
If the Bears do come away with a tight end on Tuesday, look for it to be Alie-Cox, or someone like him.