Bears Send Two First-Round Picks for Jeffery Simmons and His $100M Guarantee: The Cap Math

Ryan Poles added another key piece to the already stacked Chicago Bears defense by trading for All-Pro defensive tackle, Jeffery Simmons. The Bears sent their 2027 and 2028 first-rounder to the Tennessee Titans and a 2027 fourth-round pick to acquire Simmons and a 2028 fifth-round pick.

The 5-2 Bears believe this is their year, and Poles pounced on the chance to sign one of the best D tackles in football. Simmons has four Pro Bowl and three All-Pro selections on his CV.

In 2026, Simmons racked up 38 combined tackles, 4 sacks, 3 pass deflections, and a touchdown for the 1-6 Titans.

Simmons has the same number of sacks as Bears corner Kyler Gordon and defensive back Austin Booker. He ranks second in tackles behind rookie safety Dillon Thieneman—level with linebacker Devin Bush.

Even though Simmons joined a better team, the 29-year-old found it tough to leave his family behind in Music City.

The love I have for the city of Nashville is unmatched. For 8 years I have poured everything in me into Nashville and the Titans organization. Nashville became home. A place where I grew as a player, man, father, and a LEADER. I always pictured myself finishing what I started here, bringing winning football back to Nashville, and continuing to build something special with the Titans.

Jeffery Simmons wrote on social media via Jacob Bowman of Tennessee media.

Seeing this just breaks my heart even more. Jeff did not want to leave and never should have. Jeff was going to retire as a Titan if he had it his way. Maybe he can go win a ring in Chicago and come back at the tail end of his career, but I wouldn’t blame him if he never does. To @GrindSimmons94: Thank you for being the heart and soul of this team for 8 years. You helped show us what it looks like to be a competitor, even in the face of adversity. You showed us how important it is to give back to your community. You showed us that the most important thing is to keep your faith in God and trust in Him no matter where life takes you. I’ve got a lot of love for you bro! I was lucky enough to meet you back in October of 2021 and I’ll never forget that. Go continue to be great in Chicago! Go win a ring brother, you absolutely freaking deserve it. #TitanUp forever💙⚔️

— Jacob Bowman (@BowmanTalksNFL) October 30, 2026

The Titans drafted Simmons with the 19^th overall pick. He recorded 239 tackles, 72 TFLs, 31 passes defensed, and 46.5 sacks in 106 games with the Titans.

Simmons joins a Bears D-line that’s set to welcome back Pro Bowl defensive end Montez Sweat after a two-game suspension. He will line up alongside All-Pro DT Grady Jarrett.

Simmons landed in Chicago a couple of days ago and went straight to work. Reporters asked defensive coordinator Dennis Allen whether Simmons would make his debut in Week 8 against the Seattle Seahawks.

Dennis Allen says they will see what Jeffery Simmons can learn and digest in a short period of time in terms of him playing on Monday night.

Zack Pearson of 247 Sports tweeted

Dennis Allen says they will see what Jeffery Simmons can learn and digest in a short period of time in terms of him playing on Monday night. Also says a player like Simmons being disruptive will free up other guys as well. #Bears

— Zack Pearson (@Zack_Pearson) October 30, 2026

Simmons is 1-1 against the Seahawks in his career, and has recorded three total tackles.

The impact of Jeffery Simmons’ contract on the Bears’ salary cap

Jeffery Simmons signed a three-year, $105.8 million contract extension with the Titans in June. He instantly became one of the best-paid DTs in history.

Before the trade, the Bears had less than $10 million in cap space. The trade reduced the cap space to less than $3 million.

Despite the amount, the Bears can still cover Simmons’ salary. According to Over the Cap, they are taking on a major expense that does not kick in until next season. They will owe him around $7.9 million for the rest of the 2026 season, per OTC.

It works but it’s kind of a long (Hypothetical) Awnser … Bears have about $9.2 million in available cap space. JS 2026 base salary is $13 million, but the Bears would only take on what’s left to be paid. With 11 salary weeks remaining, that’s roughly $7.9 million. That amount decreases the later a trade happens. ( I know you already know this Greg) Titans keeps the cap charges for signing bonuses it already paid. Bears wouldn’t inherit JS entire titans cap hit. That means the Bears could potentially fit him into their existing space, although having only about $1.3 million left would be tight. They’d likely want another move to create room for injuries and roster additions. Next season If the Bears move on from Sweat, Jarrett AND Jaylon with how he’s been struggling on the field before their 2027 roster bonuses, that creates about $50.5M in cap savings. JS estimated $22.55M hit leaves roughly $27.95M before replacements and other roster needs. The Bears could pay Caleb upfront and spread the cap hit. Example: a $100M signing bonus spread over 5 years + $10M salary = a $30M cap hit in 2028. Add Simmons’ estimated $30.9M, that’s $60.9M combined. Hypothetical, but workable if the rest of the roster fits. a potential (hypothetical) path to paying both. It depends on the contract structures and finding affordable replacements & more than Likely Mid Round Rookies who can actually play. Also A LOT of agreements from everyone that they know the money is coming post Hopeful Championship .

— PAT THE DESIGNER (@PatTheDesigner) October 28, 2026

The Bears are in the market for a pass rusher

Poles isn’t finished shopping yet. According to reports from NFL Network’s Ian Rapoport and Sports Illustrated’s Albert Breer, the Bears could reunite with All-Pro edge Khalil Mack.

With the Chargers being winless in six games, they are expected to part ways with the veteran edge who spent four seasons in the Windy City. The 35-year-old has accumulated 19 tackles, 3 sacks, and 5 TFLs in 2026.

Khalil Mack trade rumors UPDATES: Bears are deep in talks to acquire Khalil Mack and deal could get done soon, per @esidery Likely cost a 5th rounder. Bears have 3: 2027 5th (Falcons) 2028 5th (Titans) 2028 5th (Bears) Trade would require minor restructure. https://t.co/ifeIJlhqiw

— Die-Hard Chicago (@DieHard_Chicago) October 30, 2026

Mack nearly retired during the offseason. 2026 could likely be his final year in Pro Football. If so, a move to Chicago sounds like the perfect story for him.

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