There are days when I admittedly refuse to believe this trade happened for the Chicago Bears. The size, scope, and historic impact October 29th, 2026, will have throughout the league for the foreseeable future is almost impossible to comprehend. A deal many people assumed general manager Ryan Poles would never be bold enough to attempt.
Except, he’s always been this bold. He simply waited for the right time, right price, and only after all his homework was completed and reviewed with their staff.
A trade that assessed every possible angle and weighed risk vs. reward more than anything else.
Detailing back to the spring of this year, I maintained the Bears would be poised to strike on a major move to bolster their defensive line. This scenario has been one I’ve tracked for the better part of the past calendar year. Many, many big names were floated around behind the scenes. Including Maxx Crosby, of whom the Bears mentioned publicly as a player they checked in on. It always came down to Ryan Poles’ comfort level with the price tag presented.
Ironically, it was the least likely option on paper for me that wound up becoming reality. Not a single defensive tackle traded has ever commanded more than a single first-round pick throughout the modern Super Bowl and draft era. Very few players have ever signed a lengthy record-setting contract with their home team only to be shipped off elsewhere before the trade deadline.
That paragraph might be the reason Ryan Poles pulled this trigger then and there. Not a single team in the league was made aware of Jeffery Simmons’ availability until only after the trade was announced. Ryan Poles mentioned in his press conference that he eyeballed Jeffery Simmons for the past few years. He called current Tennessee Titans general manager Mike Borgonzi several times dating back to 2025 and checked in on Simmons’ availability. The answer usually received: “No, Ryan.”
Fast forward to late October of 2026. The Bears are rolling and have a legit MVP-caliber quarterback in Caleb Williams, priming the Monsters of the Midway for a potential run at the Super Bowl. Ben Johnson, the Bears’ head coach and dual-major graduate of mathematics and computer science from North Carolina at Chapel Hill, has the vision on how to get Chicago to the promised land. Dennis Allen, their mad scientist of a defensive coordinator, mixed and matched to the best of their abilities. Everything was trending in the right direction.
There was just one big problem facing the Bears. They didn’t have a destroyer of worlds for the interior of their defense. A kind of player Ryan Poles referenced the last five Super Bowl champs having on their rosters.
2025 – Seattle Seahawks (Leonard Williams)
2024 – Philadelphia Eagles (Jalen Carter & Jordan Davis)
2022 & 2023 – Kansas City Chiefs (Chris Jones)
2021 – Los Angeles Rams (Aaron Donald)
2020 – Tampa Bay Buccaneers (Vita Vea & Ndamukong Suh)
Meanwhile, the Tennessee Titans were facing the exact opposite situation. Endless debates are being entertained after having just one win up to this point in 2026. A season that can be best described as a lost voyage featuring yet another head coach — Robert Saleh — as their captain, paired with a quarterback and helmsman they didn’t handpick themselves. A sailboat with patchwork rigging and a broken rudder but a fine motor in reserve named Jeffery Simmons. The very kind of motor Ryan Poles sought after for his defense.
Determined to get his white whale, Ryan Poles called Mike Borgonzi once again on October 28th. This time, per Jay Glazer, he straight up offered two first-round picks before even beginning their conversation in earnest. Usually you’d contact the football front office of your primary target, ask, “What are your demands?” Then circle back once your own staff is briefed. Ryan went straight to business and threw out all traditional negotiation tactics. Similar to a method when abandoning the traditional second interview for Ben Johnson before hiring him as head coach.
Mike Borgonzi never thought he’d receive a Myles Garrett-level package for Jeffery Simmons. A true Godfather offer that you cannot refuse on first glance. He knew as much as anyone the precedent Ryan Poles’ offer stood to redefine. True to their own principles, Mike told Ryan he’d call him later after mulling over this massive deal. The next morning he briefed Titans owner Amy Strunk along with their executive leadership and Robert Saleh about his latest offer in hand.
Interestingly enough, the Bears weren’t the only franchise attempting to poach Simmons away. Prior to this meeting at the Titans’ ownership level, John Harbaugh of the New York Giants attempted to contact Amy Strunk directly, of which Strunk deferred back to Borgonzi and the terms of the conversation were discussed. It has been suggested John Harbaugh’s offer would not have trumped what the Bears were willing to do.
Then there are these potential considerations when discussing the human element – where were the Bears headed this season in comparison to the Giants? Where would Jeffery Simmons, a player beloved from ownership on down, get their best chance to win a Super Bowl? And how would they go about doing right by Big Jeff?
Early on Tuesday morning, the Titans finalized their decision. Todd France, Jeffery Simmons’ agent, called his client later that day. It was to inform him of his immediate departure for Halas Hall on a short fused flight to Chicago O’Hare. Jeffery Simmons informed his family, said his “see you later’s” to his daughter, and reported to Bears HQ to finalize their physical that very evening. Two practices and a few days later he would make his regular season debut for the Chicago Bears at Lumen Field in Seattle, WA.
Of course, the results have been immediate. The Bears are, finally, generating pressure with just their front four while keeping their defensive backs in coverage. That doesn’t mean Dennis Allen won’t blitz anymore; it just means he can keep those aces up his sleeves more often. Prior to “El Jefe’s” arrival, the Bears were blitzing more than anyone else not named the Minnesota Vikings out of necessity.
Through the first seven weeks, the Bears defensive line was unable to register more than two full sacks on their own for any single game. Their pass-rush win rate was roughly 25%, which ranked near the bottom of the league. Following Jeffery Simmons’ arrival the Bears defensive line has exploded – against the Seahawks alone that unit won a whopping 53% of their matchups and Montez Sweat had two of his three sacks taken away due to penalties. Against the Tampa Bay Buccaneers, the Bears’ front four registered four sacks between five players.
Blasting quarterbacks isn’t the only feat Big Jeff is capable of performing. The run defense has been much improved too – for the first seven weeks, the Bears ranked 26th in defensive EPA (-0.01). Since his arrival in week eight that has improved to 19th (-0.07). There is optimism this group will break the top 15 once they return from their bye.
Let’s now talk about the sheer cost of this trade and how it’s not the most expensive ever for a defensive tackle. We will use the Draft Pick Trade Value Chart as designed by Mike McCoy and famously used by Jimmy Johnson as reference.
Shortly before the start of the 2026 NFL Draft, the Cincinnati Bengals struck a deal to send their 10th overall pick, which netted Dexter Lawrence in return. On face value alone, the 10th overall is worth 1300 points. And this isn’t a future draft pick – it’s locked in at its current spot. Which then gave the Giants two picks within the top ten of the draft order at 5th (1700) and 10th (1300) to open the first round. Those picks combined are worth 3000 points.
In direct comparison, while the Bears are surrendering more draft picks in total, the points and value thereof take a steep dive. A future first round pick, which comes at a “future discount” once past 32nd overall (590) will be roughly 500 points. Or the equivalent of having pick #40 overall. Any draft pick past one full year into the future are valued even less. Common sense suggests future picks are unpredictable and can vary greatly once the games are played.
If spotting a generous boost and treating all future picks the same the Bears have given up two 1sts (500 each) and a 4th (33) while netting a 2028 5th (15) along with Jeffery Simmons. The math comes out to 1018 points against the Jimmy Johnson Value Chart. That is less than the 1300 points of value surrendered by the Bengals for Sexy Dexy. A trade that has yielded good results of its own.
So… what about the other massive trades involving defensive stars and multiple first-round picks?
2025 – Sauce Gardner (Indianapolis Colts)
2025 – Micah Parsons (Green Bay Packers)
2019 – Jalen Ramsey (Los Angeles Rams)
2019 – Jamal Adams (Seattle Seahawks)
2018 – Khalil Mack (Chicago Bears)
The Bears saw decent individual results but not elite team results from their Khalil Mack trade of 2018. The Rams would win a Super Bowl with Jalen Ramsey being a major reason why. Micah Parsons has been injured and right now is an incomplete grade. The Jamal Adams deal turned into a “flash in the pan,” a hot start with an NFL record 9.5 sacks registered by a DB only to fizzle out after making just 34 total appearances in 4 seasons. The Sauce Gardner deal has been an unmitigated disaster.
Yet there is one significant difference between the Jeffery Simmons deal and all those previously referenced – he was signed to a long-term contract, of which the Titans have already paid off a good chunk in advance. All those other deals required their new teams to negotiate a new contract prior to their respective arrivals. And in comparison the Jeffery Simmons contract rates in with a significant discount.
Here are his full financial terms for their contract listed on Over the Cap.
Starting in 2027, he will be owed $21.4M in base salary and averages $25.38M for the remainder of his contract running through 2030. There is also an out still available for 2030, which drops his final season for $0 in dead cap. We all know Caleb Williams will likely reset the market at QB once his extension is finalized in the near future. As far as I’m concerned, having the #1 ranked defensive tackle in the league at the value of just over $25M per year is a steal. There’s no guesswork involved at all.
This trade wasn’t made with only 2026 in mind. True to Ryan Poles’ philosophies, he won’t make a move that will hamstring his future severely and force him to win it all for just one season. Jeffery Simmons is under contract for the Bears until 2030 and plays a brand of ball which ages well past their 30th birthday next season. Overall, the Bears are still loaded with healthy amounts of cap space, draft capital, and have budding stars playing on their rookie contracts. It’s the kind of execution few general managers ever get to witness for their rebuilds.
It all comes down to making this trade count. Super Bowl Championships are the only acceptable outcome to fully justify this trade for Chicago. No matter what else happens in Tennessee, much like the deal involving pick #1 overall shipped to the Carolina Panthers in 2023, this is Ryan Poles’ attempt to draw an “Out” to complete his hand at taking back the Lombardi Trophy. He’s pushed all his chips to the table’s center and made his call.
