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Chicago Bears Go All-In: Jeffery Simmons Deal Signals Super Bowl Intentions, Khalil Mack Should Be Next

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Ryan Poles feels it. The Chicago Bears have the foundation to contend with any team, any time, anywhere this season, with Ben Johnson guiding Caleb Williams, who has unlocked the offense in his second year under Johnson. Dennis Allen has proven he can elevate a defense that lacks overall talent, but as we look ahead to the 2026-27 NFL season, the Bears are no longer concerned about competing; they’re trying to win a Super Bowl.

Bears Blockbuster Trade for Jeffery Simmons

The intentions were made clear on Thursday, when Poles shocked the league by trading for the best defensive tackle in the NFL. Jeffery Simmons will now anchor Chicago’s D-line after the Bears’ GM sent the Tennessee Titans a 2027 and 2028 first-round pick and a 2027 fourth-round pick to complete the deal. It’s a lofty price for the 29-year-old, but few teams are willing to make a move like this.

It speaks to the team’s confidence in Williams, as any intelligent front office is aggressive while their star quarterback is still under his rookie contract. But why stop at Simmons?

Before the blockbuster Simmons trade, the popular name connected to the Bears was Khalil Mack. He may not be the superstar edge rusher he was when the Bears pulled off a stunner heading into the 2018 season, but Mack can still give opposing teams headaches. Now imagine him lined up opposite Montez Sweat, with Simmons in the middle wreaking havoc.

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What’s the Most You’d Trade for Khalil Mack?

On the latest episode of J-Mack Reacts with Jason McKie, the former Bears fullback was cautious about Mack’s price. Yet it aligns with what other NFL analysts expect to cost to acquire the current San Diego Chargers defensive lineman.

“I would say, right what we were talking about, a fifth. I wouldn’t go higher than that. You know what I’m saying? And I’m a fan of Khalil Mack too. You gotta take your feelings out of it. You got to put your GM hat on; I got to put my Ryan Poles hat on, right? You know what I’m saying? I just wouldn’t go higher than that just because of the age.

How long can he help you? You know what I’m saying? Is it just, is it this year? You’re trying to go all in this year and say, you know what, we got a chance to be really special. We want to make some noise in the playoffs and not just get to the playoffs and we may need a guy, you know, like Khalil Mack in the rotation, more pressure on the quarterback to help us get over that hump.

So, I just think, you know, Ryan Poles is going to do what he has done since his tenure as GM, what makes sense for the Bears, not just in the present, but mostly in the future.”

That answer was before Poles made a franchise-altering trade for Simmons. He showed that while keeping an eye on the future is important, capitalizing on the present reigns supreme. The future is now. Simmons was the big piece the Bears needed. Mack could be the extra edge that might actually get them over the top.

Don’t miss J-Mack Reacts, every week with Jason McKie.

Aldo Soto
Aldo Soto
With a journalism degree from Eastern Illinois University and a decade of Cubs reporting, my work has appeared on 670 The Score, ESPN 1000, and the Pinwheels and Ivy Podcast. I cover Cubs news and analysis for Sports Mockery, including roster moves, game breakdowns, and prospect development.

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