The Chicago Bears made one of the biggest moves of the 2026 NFL trade deadline, acquiring Tennessee Titans defensive tackle Jeffery Simmons and a fifth-round pick in 2028 in exchange for two first-round picks and a fourth-round selection.
While the price is steep, general manager Ryan Poles is betting that adding the four-time Pro Bowler and three-time All-Pro can help Chicago become a legitimate Super Bowl contender.
The deal belongs in the same conversation as several other blockbuster trades involving elite NFL talent. For a trade to qualify as a “blockbuster deal” in this comparison, at least one team must surrender a first-round pick.
Bears’ Jeffery Simmons Trade Joins Recent NFL Blockbuster Deals
Here is how Chicago’s acquisition of Jeffery Simmons compares with six other major NFL trades involving first-round draft picks.
Indianapolis Colts trade for Sauce Gardner
In November 2025, Indianapolis acquired cornerback Sauce Gardner from the New York Jets in exchange for the 2026 and 2027 first-round picks, as well as wide receiver Adonai Mitchell. Gardner was a two-time First Team All-Pro cornerback who, at the time, looked to help the 7-2 Colts make a playoff push.
Dallas Cowboys trade for Quinnen Williams
Out of all the trades that will be mentioned, this is the most comparable to the Simmons trade, considering Quinnen Williams plays the same position. Back in November, the Cowboys acquired Williams from the New York Jets, sending a 2026 second-round pick, a 2027 first-round pick, and defensive tackle Mazi Smith.
Green Bay Packers trade for Micah Parsons
The Packers made a splash in August 2025, acquiring edge rusher Micah Parsons from Dallas in exchange for defensive tackle Kenny Clark and first-round picks in 2026 and 2027. Green Bay then handed Parsons a four-year, $188 million contract which includes $120 million fully guaranteed, making him the highest-paid non-quarterback in NFL history at the time.
Cincinnati Bengals Trade for Dexter Lawrence
Another trade involving a defensive tackle, the Bengals traded the 10th overall pick in 2026 for New York Giants defensive tackle Dexter Lawrence, who’s been a game-changing acquisition for Cincinnati.
User @ilannfl18 pointed out something interesting when comparing the Simmons and Lawrence trades:
“Dexter Lawrence traded for 10th overall pick 10th overall pick value: 1300
Jeffrey Simmons and a 5th traded for 2 firsts, a 4th, extended through 2030
24th overall pick value: 740 2028 24th overall pick value: 340 2027 4th round pick – 2028 5th round pick value: 40 ≈1120
Roughly very similar prices. People seemed to think Lawrence price was fair. This one is too.”
New England Patriots trade for A.J. Brown
The Patriots acquired wide receiver A.J. Brown from the Philadelphia Eagles in 2026, sending a 2028 first-round pick and a 2027 fifth-round pick. Although Brown hasn’t done much this season.
Los Angeles Rams trade for Myles Garrett and Trent McDuffie
The Rams really went all in, acquiring Myles Garrett from the Cleveland Browns in exchange for edge rusher Jared Verse, a 2027 first-round pick, a 2028 second-round pick, and a 2029 third-round pick. Garrett was coming off a record-setting 23-sack season in 2025, but like Brown, hasn’t done much so far this season in Los Angeles.
The Rams also traded for Kansas City Chiefs cornerback Trent McDuffie, sending the 29th overall pick, a fifth-round pick, a sixth-round pick in the 2026 NFL Draft, and a third-rounder in 2027. Los Angeles then handed McDuffie a four-year, $124 million extension that includes $100 million in guaranteed money.
Simmons’ Contract Through 2030 Gives Bears a Significant Advantage
One of the most important details of Chicago’s trade is Simmons’ contract. He signed a three-year, $105.8 million extension in June 2026 and is under contract through 2030.
That gives the Bears something particularly valuable after surrendering two first-round picks: contractual certainty.
Spotrac’s Mike Ginnitti outlined the financial commitment Chicago now faces since they traded for Simmons:
2026: $7.9M
2027: $26.9M
2028: $29.8M
2029: $28M
2030: $32M
It allows the Bears to win a Super Bowl now, and worry about handing players like Caleb Williams, Colston Loveland, and Luther Burden extensions later.
Comparing the Bears-Jeffery Simmons Trade to Other Blockbuster Deals