Monday, December 22, 2025

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Chicago Bears Trade Options Could Be Plentiful Next Month

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Chicago Bears trade ideas aren’t likely to become a talking point anytime soon. The team is too focused on continuing to dig out of their early hole from the start of this season. They got some much-needed momentum with that wild escape from Denver. Now it’s a question of whether they can take advantage of it. The defense is great as expected. It’s the offense that needs work. A lot of work. That said though, GM Ryan Pace is always keeping his ears open for possible moves.

By this point, the landscape of the NFL is coming a little more into focus. The good teams and the “maybe” teams are separating themselves from the “obviously bad” teams. It is those in the latter category that bear watching over the next month and a half. The Miami Dolphins have already blown up most of their original core. Laremy Tunsil? Kenny Stills? Minkah Fitzpatrick? Already traded for high draft choices.

Others may not be far behind if things continue to spiral. Are there any names out there the Bears would or should have interest in? Here is a shortlist of ones to keep in mind as the trade deadline at the end of October draws closer.

Chicago Bears trade deadline targets to watch

Leonard Williams (New York Jets)

Another year, another apparent reality of the Jets being awful. They have a new regime in charge though. At 0-2 and their quarterback laid up with mono, it feels like this team isn’t going to rebound anytime soon. They could be out of the playoff hunt before October is even halfway concluded. This may compel GM Joe Douglas to start stockpiling resources for next offseason. Leonard Williams could be a guy they decide to unload.

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The big defensive lineman has been a source of irritation for many in New York. Not because he’s bad but more because he’s inconsistent. He’ll flash one week with a look of dominance and then disappear the next. The Jets may wish to just move on and start fresh. Williams is 25-years old and played at a Pro Bowl level in 2016. Jay Rodgers is one of the best defensive line coaches in football. This could be a lowkey great move for an already lethal front seven.

The money will be an obstacle though. Williams is playing on his 5th-year option at over $14 million. So either the Bears would be renting him for half a season or working to find a creative way to extend him long-term while stashing enough money for Eddie Jackson next offseason.

Evan Engram (New York Giants)

Adam Shaheen showed encouraging signs of improvement in Denver. Trey Burton finally returned from his groin ordeal. Despite this, the Bears still aren’t getting enough out of their tight ends. Given how important the position is to the success of Nagy’s offense, it would make sense they’d be on the lookout for potential options. Evan Engram is one that popped on the radar before the season.

It was reported that he wasn’t viewed as the best fit for the offense head coach Pat Shurmur is running. Thus far he’s been one of their most reliable pass targets with 164 yards and a touchdown. However, the Giants are 0-2 and now turning in desperation to their rookie top draft choice Daniel Jones at quarterback. If their spiral continues, Dave Gettleman could look to dump another offensive piece he didn’t draft to build towards the future.

William Jackson III (Cincinnati Bengals)

Injury shortcircuited the beginning of his career but Jackson has since developed into a quality cornerback for the Cincinnati Bengals. Thus far in 2019, he’s allowed only 50% of the passes thrown his way to be completed. He’s also the only member of the defense with an interception. This despite playing behind a defensive front that has just four sacks in two games. He has size, length, speed and instinct that is hard to ignore.

The Bears have looming questions at cornerback. Prince Amukamara is getting deeper into his 30s and may be a cap casualty in 2020. The depth behind him is highly questionable with Kevin Toliver and Duke Shelley being their best options at this point. Jackson III would make for a perfect bridge beyond the Amukamara era and the Bears could have him this year at a cheap price with his 5th-year option in effect for next year as well.

Chad Kelly (Indianapolis Colts)

Mitch Trubisky is still the quarterback. That is unlikely to change. However, the Bears have at least been given enough reason to be concerned about his lack of progress. Finding an outright replacement at this juncture is impossible. Their best-case scenario is to find a cheap option with upside who might at least send a message to Trubisky that he better start picking his game up or things are going to change.

Chad Kelly would make sense.

Now a lot of people might scoff at this. They have good reason to. Kelly has a history of delinquent behavior dating back to his college years. He has a streak of immaturity miles long. However, everybody grows up eventually. Kelly would’ve been a top 50 draft choice had he stayed out of trouble. His arm strength and accuracy are top notch. The guy was a gamer during his run at Ole Miss and he’s got NFL blood in his veins, being the nephew of Hall of Famer Jim Kelly.

With Jacoby Brissett and Brian Hoyer firmly in place ahead of him, the Colts might be willing to let him go for cheap.

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