The Chicago Bears have done pretty much all they can to prepare the roster for a big 2026 season. Despite monitoring the various markets, general manager Ryan Poles didn’t make any bold moves. He managed his resources carefully and got the best players possible. All things considered, he did pretty well. The defense is younger and faster. The offense is younger, faster, and deeper. Everything was accomplished while maintaining flexible finances and enough draft capital for the future.
Still, it feels like the Bears are one move short of really being a team that has a legitimate chance to chase a Super Bowl. Right now, they aren’t considered true favorites in the NFC like Seattle, Los Angeles, or Philadelphia. They need something more to hit that extra gear. If they’re to find something like that, it will have to be on the trade market. Right now, no such possibilities exist. However, looking ahead to the deadline in November, here are a few names that could be up for grabs and had for affordable prices.
Chicago Bears trades that would instantly make them better.
3rd round pick to Arizona for EDGE Josh Sweat
It is an open secret at this point that the former Super Bowl champion isn’t happy. The coach Sweat signed on to play for, Jonathan Gannon, was fired after last season. That and releasing quarterback Kyler Murray put Arizona squarely on the path to a rebuild. Sweat didn’t sign up for that, and there have been rumblings for months that the edge rusher might eventually push his way out of town. Having three years left on his contract makes him a more attractive target for the Bears. A 3rd round pick feels reasonable since he’s 29 and wants out. Arizona gets something to help the rebuild, and Chicago gets a legitimate double-digit sack option.
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2nd round pick in 2027 to Pittsburgh for EDGE T.J. Watt
The Steelers really put themselves in a cap bind by extending Nate Herbig. They are now paying three of their edge rushers big money, along with Alex Highsmith and Watt. This is why speculation has persisted that one of them will eventually be traded. Watt is the most expensive of the group at $41 million per year. He’s also coming off one of his worst seasons in years with seven sacks in 14 games. It is believed he is on the decline at age 31. If the Steelers don’t get out of the gates strong, they may decide to unload him. Even at his age, Watt is worth the gamble. Few pass rushers can take over games as he can. Playing in a more diverse and exotic scheme like Chicago’s could make life easier for him while he makes life easier for everybody else.
4th round pick in 2027 and 5th round pick in 2028 to Indianapolis for RB Jonathan Taylor
ESPN predicted that the Chicago Bears would be the landing spot for the All-Pro running back in a trade this year. This presumes the Indianapolis Colts struggle out of the gates. Taylor has one year left on his contract, and they might be reluctant to extend him again, even though he’s still just 26. Ben Johnson won’t have any concerns about that. Taylor is the type of stud running back who would be a demon in this rushing scheme. Remember, he’s posted at least 1400 yards in three of the past five seasons. That was despite playing with below-average quarterbacks. Put him with Caleb Williams, and it could get wild.
Conditional 3rd round pick in 2027 for Baltimore DT Nnamdi Madubuike
Baltimore faces serious salary cap issues in 2027, with projections of being over $64 million in the red. That means they will have to unload at least one of their biggest contracts. Madubuike suffered a nasty neck injury last season, leaving his status moving forward uncertain. The Ravens could use that as an excuse to move him out. A trade would net them $11 million in cap space. When healthy, Madubuike was one of the best interior pass rushers in the NFL. The Bears have badly needed that for some time. A conditional 3rd round pick that can become a 2nd round pick if certain health and statistical thresholds are met sounds reasonable.
Conditional 4th round pick in 2027 to Atlanta for LT Jake Matthews
It isn’t a secret that left tackle is a problematic position for the Chicago Bears. Right now, their two best options are Braxton Jones and Jedrick Wills. Free agency and the draft didn’t offer any definitive solutions. That could change if things don’t go well early for Atlanta this season. They’re facing a transition period under new general manager Ian Cunningham. He may decide to start stacking draft capital for 2027. Trading the 34-year-old Matthews feels like a possibility. He’s still good enough to fetch something decent. In this case, a conditional pick that becomes a 3rd if he starts every game and a 2nd if he makes the Pro Bowl. Chicago gets one of the better left tackles in football, fortifying their offensive line for a big second-half run.
