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ESPN insider raises possibility of major Bears trade deadline move

ByChris Pownall
May 9, 2025; Lake Forest, IL, USA; Chicago Bears defensive coordinator Dennis Allen (L), general manager Ryan Poles (C) and head coach Ben Johnson (R) observe during the Rookie Minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Images
May 9, 2025; Lake Forest, IL, USA; Chicago Bears defensive coordinator Dennis Allen (L), general manager Ryan Poles (C) and head coach Ben Johnson (R) observe during the Rookie Minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Images | IMAGN IMAGES via Reuters Connect

The Chicago Bears have been mentioned among teams preparing to make an aggressive move before the NFL trade deadline. ESPN's Courtney Cronin believes the opportunity is there, but another NFC contender just removed one of Chicago's potential targets from the market.

The Chicago Bears might be running out of time to decide how aggressive they want to get.

And after Tuesday's developments around the NFL, general manager Ryan Poles has another reason to pick up the phone.

During an October 27th appearance on ESPN Chicago's The Chicago Bears Podcast, Courtney Cronin discussed the possibility of Chicago making a significant defensive addition before the November 10th trade deadline.

Her message was pretty clear. The Bears have a legitimate opportunity to compete, and those opportunities don't last forever.

Then, shortly after the podcast was released, one of the biggest names connected to Chicago was traded.

Courtney Cronin believes Bears have reason to make aggressive trade

Cronin pointed to Caleb Williams and the advantage Chicago currently enjoys with its quarterback playing on a rookie contract.

"You can't waste this opportunity to win with a quarterback who is still on his rookie contract," Cronin said.

She also acknowledged that Poles has historically valued draft picks, making a trade involving multiple first-round selections difficult to envision.

But this isn't the same situation Chicago faced during previous rebuilding seasons.

The offense has demonstrated it can compete against quality opponents. The defense, however, still has questions along the defensive line and in the secondary.

Cronin identified those areas as potential priorities, mentioning Khalil Mack, Jeffrey Simmons and DeForest Buckner among the defensive players generating trade discussions.

There was just one problem.

Buckner wouldn't remain available much longer.

DeForest Buckner trade puts additional pressure on Bears

Later Tuesday, Indianapolis traded Buckner to the San Francisco 49ers for a 2027 fourth-round pick.

That's a relatively modest return for a three-time Pro Bowl defensive tackle who already has four sacks this season.

And Chicago had reportedly been connected to him.

NFL insider Jordan Schultz previously identified the Bears and 49ers as teams showing interest in defensive reinforcements, including Buckner.

Now San Francisco has him.

The 49ers aren't merely adding depth. They're bringing back a proven defensive lineman to strengthen an already competitive roster.

Meanwhile, the Bears are still evaluating their options.

That doesn't mean Chicago should have automatically matched San Francisco's offer. Buckner is 32 and approaching free agency.

But watching another contender acquire an established pass rusher for a fourth-round selection certainly raises questions.

Ryan Poles faces an increasingly important decision

Cronin also discussed the possibility of Chicago pursuing Mack, whose previous tenure with the Bears makes him an obvious name to watch.

Simmons would represent another significant addition, although acquiring him could require considerably more draft capital.

And Montez Sweat's return from suspension gives Chicago an opportunity to evaluate its existing pass rush before making a decision.

The Bears don't necessarily need to mortgage their future.

But with Buckner already heading to San Francisco and Seattle strengthening its offensive line by acquiring Quenton Nelson, the NFC's contenders aren't waiting around.

Poles has until November 10th to decide whether Chicago will join them.

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