Bears Go All-In On Super Bowl Run, Land Jeffery Simmons In Blockbuster Trade With Titans

This article was written by Matt Foley and published on Sport & State, a new media company founded by Clay Travis that is built around sports, culture, original voices, and live conversation.

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The Chicago Bears may not be done making moves before the Nov. 10 trade deadline, but GM Ryan Poles just pushed all his chips into the middle of the table.

In a blockbuster trade Thursday, Chicago acquired superstar defensive tackle Jeffery Simmons and a 2028 fifth-round pick from the Tennessee Titans in exchange for two first-round picks (2027 and 2028) and a 2027 fourth-rounder.

Trade: Titans are trading All Pro DT Jeffery Simmons to the Chicago Bears, per sources.

— Adam Schefter (@AdamSchefter) October 29, 2026

It’s a massive move for a 5-2 Bears team that, at times this season, has already looked like a legitimate Super Bowl contender.

As I detailed in the Morning After column this week, Chicago’s defense has been outperforming the collective talent level so far this season, and the defensive interior was a glaring weakness for the unit.

With the arrival of Simmons, Poles gives defensive coordinator Dennis Allen a bona fide game-wrecker to not only stave off the regression that was likely coming but to level up his attack.

Simmons is arguably the best defensive tackle in football. Paired with Bears DE Montez Sweat — who will return from a two-game suspension Monday night against Seattle — he’s exactly the type of interior force that can spark a deep playoff run.

Simmons was a first-team All-Pro last season, when he posted a career-best 11 sacks, and has 46.5 sacks in eight NFL seasons.

The four-time Pro Bowler has generated 38 tackles this season and 28 pressures, including 10 pressures and three sacks when double-teamed, according to Next Gen Stats. All of those statistics rank first among defensive tackles.

Leading your position in sacks and pressures when double-teamed is a clear sign of dominance, and Bears fans should be ecstatic that their front office is aggressively solving problems with the best possible answer.

Jeffery Simmons 10 Fastest Sacks since 2024: https://t.co/WSpz3hnfHE

— Ryan Paganetti (@RyanPaganetti) October 29, 2026

The Money

Simmons signed a three-year, $105.8 million extension in June, averaging $35.3 million annually in new money and keeping him under contract through 2030.

That’s a substantial long-term financial commitment, particularly with Caleb Williams coming due for a massive payday, but according to Albert Breer, Tennessee already paid Simmons’ bonus money.

That means Chicago will only owe him $7.94 million for the rest of this season and $26.95 million in 2027. Chicago’s not just renting him for a playoff run, and it’s a relatively team-friendly deal, despite Simmons being owed $124.7 million through 2030.

How it happened

Here’s how the sausage gets made, folks.

Titans GM Mike Borgonzi and Bears GM Ryan Poles worked together in Kansas City from 2009-21, and actually were together at Boston College in 2007 when Poles was a player and Borgonzi was a young assistant.

High level of trust b/w the two was a big factor in the Simmons deal.

— Albert Breer (@AlbertBreer) October 29, 2026

Evidently, Williams doesn’t hold a grudge …

THROWBACK: When #Bears rookie Caleb Williams told #Titans star Jeffrey Simmons to ‘CHECK THE SCOREBOARD’ at the end of the game.

This came shortly after Simmons made fun of Caleb‘s nails: “Painted nails. I can’t wait to say that to him”

Teammates now ???? https://t.co/ZElCJqhSms

— MLFootball (@MLFootball) October 29, 2026

For Tennessee …

The deal signals a full commitment to rebuilding. At 1-6, the Titans are sacrificing their defensive cornerstone for a massive infusion of draft capital.

It’s a potentially franchise-altering haul, and it’s absolutely the right decision. But as my colleague Chad Withrow points out, it’s not without risk.

Getting two 1st round picks in return for Simmons is a MAJOR coup for the #Titans . The current problem is that the guy in charge of making those first round picks hasn’t been particularly good at the whole drafting players thing.

— Chad Withrow (@TheChadWithrow) October 29, 2026

Titans GM Mike Borgonzi now faces the pressure of turning those premium picks into actual difference-makers.

Chicago is loading up to win now. Tennessee is betting on better days tomorrow (if they can just fix that tricky Cam Ward problem …)

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