Caleb Williams’ Rookie Contract Makes Bears’ Trade for Jeffery Simmons a Home Run

The Chicago Bears picked the perfect time to go all-in with the acquisition of star defensive tackle Jeffery Simmons.

Chicago Bears quarterback Caleb Williams (18) celebrates after defeating the Cleveland Browns at Soldier Field. Mandatory Credit: David Banks-Imagn Images | IMAGN IMAGES via Reuters Connect

The Chicago Bears confirmed that they are indeed all-in on the 2026 season after the team acquired Jeffery Simmons in a blockbuster trade on Thursday morning.

Not only did the Bears give up two of first-round picks in the trade, but they also are taking on Simmons' hefty contract, which ranks fourth in total value at the position.

Simmons is under contract through 2030 and the Bears will be on the hook for $7.9 million in 2026, $26.9 million in 2027, $29.8 million in 2028, $28 million in 2029 and $32 million in 2030.

However, it's important to note that Simmons doesn't have any guaranteed money left after 2027, so there doesn't have to be a long-term commitment here if things don't pan out.

Williams' contract makes Simmons trade a home run

Tennessee Titans defensive tackle Jeffery Simmons (98) storms the field before the game against the Cleveland Browns at Nissan Stadium in Nashville, Tenn., Sunday, Oct. 25, 2026. | USA TODAY Network via Reuters Connect

The most ideal time for an NFL team to go all-in for a Super Bowl is when a quarterback is on a rookie contract because there's more flexibility in the salary cap without the quarterback bringing in a massive sum of money. That obviously allows teams to make massive improvements at positions of need.

And that's the position the Bears find themselves in 2026 and in the next few years after this one, when Caleb Williams will still be on a cheap rookie deal.

Williams accounts for a cap hit of just $10.7 million in 2026 and $12.5 million in 2027. His salary is projected to balloon in 2028 to $29.9 million because of the fifth-year option, but that's still a reasonable price for a top-notch quarterback, as Williams' eventual extension could hit $60 million per year.

So, it comes as no surprise that the Bears are shooting for the stars right now. Also making it easier is the fact that Williams appears to be ascending toward elite status and having a quarterback at an elite level is the biggest puzzle piece.

With Williams' fifth-year option kicking in for 2028, that means the first year of his new deal won't hit until 2029, which is the second-to-last year of Simmons' current deal, assuming the Bears don't extend or cut him before then.

And, Simmons' contract will be in its final year in 2030, so the Bears will have him off the books two years into Williams' extension.

Also bear in mind that Simmons doesn't have guaranteed money left on his deal, so there doesn't have to be a long-term commitment here if things don't pan out.

One more thing to take note of is the $7.9 million the Bears are on the hook for this season. That means the Bears still have some flexibility to make another significant move, which fans will be hoping comes at edge rusher.