What Jeffery Simmons Trade Can Mean for the Future of Bears Roster

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The future of the Bears in terms of the salary cap after their trade for Jeffery Simmons is more of alteration than overhaul. Adding a $105 million deal to the payroll can things, but it's all relative in a league that keeps making gobs of money.
Some could look at their cap situation for coming years and wonder what they're doing when they have to pay Caleb Williams an extension, but his deal is always under consideration and their contract negotiator, Matt Feinstein has weighed this out in planning.
“All of those things we started a while ago, just researching what does that look like and how does it impact this?" GM Ryan Poles said. "Because you do have to work both directions.
"We’ve got a ways to go and get through the season before we get to that, but we're always forecasting how do these different things and events and contracts fit together. I have an unbelievable analytics program. I have an unbelievable guy in Matt Feinstein, who does really good work helping us understand the impact that all of those things have on us.”
The reason it means alterations is it is going to mean some players who may have been back, won't be in the future. Then again, some of these players may not have figured into their future. It's all open to speculation now, but based on their performances it is easy to see what could happen.
Feinstein and Poles are not the only ones who can forecast.
Mahomes cap hits the next 3 years:
— Al Bundy (@Maratea20G) October 27, 2026
2027: $90M
2028: $86M
2029: $83M
Remember this when everyone is throwing around these pipe dreams of signing big name players.
Capping the future
The Bears could actually add someone still this year but it would need to be at a low rate. They have $1.8 million left in cap space, according to Overthecap.com. Adding anyone else of significance now would mean more contract restructuring for some players.
As for the future, the Bears now are over the 2027 salary cap by $23.6 million, but it's $32.8 million in terms of effective cap space. This is a more relevant figure becuae it includes what they would have after signing at least 51 players and a projected rookie class. There are only four teams in bigger salary cap holes for 2027 than the Bears.
The Bears just paid two first-round picks for Jeffery Simmons, and the bigger price is the contract.
— check coula (@checkcoula) October 29, 2026
Chicago gets the All-Pro DT plus a 2028 5th. Tennessee gets 2027 and 2028 1sts plus a 2027 4th.
Simmons, 29: 3 years, $105.8M, $100M guaranteed, through 2030. #NFL #Bears pic.twitter.com/mGaXYuXQsz
Obviously, they need to make up that money somewhere.
Cutting Montez Sweat, Jaylon Johnson, Cole Kmet, Grady Jarrett, T.J. Edwards, Dayo Odeyingbo, and Tyson Bagent would get them well below, largely because Sweat gives them $21 million in cap savings and would now only stick them with $4.8 million in dead cap space. Johnson's deal would provide only about $7 million in total cap savings after dead cap and Jarrett about $9.5 million. Kmet's deal would be about $4.6 million in total savings, Bagent $3.75 million, Odeyingbo $3.5 and Edwards $2.8 million.
Plenty of cash exists but it will create a drastically altered roster. Then again, some would look at the production some of these players have had and would expect some sort of roster move.
The important year is 2028 because this is the cap more affected by Caleb Williams' deal. They've been planning for this as they have the third-most cap space in the league available even after Simmons' contract is weighed into all of it.
How He Built the BEST #Bears Team of my ENTIRE Life https://t.co/Mj4anZW1Vl
— Swift Sports Network (@SwiftyNetwork) October 31, 2026
In 2028 great change was already coming
In 2028, they only have 12 starters under contract, assuming Willams' fifth-year option is picked up. Kyler Gordon, Darnell Wright, Simmons, Colston Loveland, Coby Bryant, D'Andre Swift, Devin Bush, Dillon Thieneman, Luther Burden III, Ozzy Trapilo, Trapilo and possible future starting center Logan Jones would be those players besides Williams.
None of those players whose departure would provide relief next year are among players who would be back in 2028, unless they got extensions.
NFL revenue keeps climbing — $301.2M cap is up ~7.9% from last year. Players cashing in big time.📊
— Data Of Statistics (@DataOfStats) February 27, 2026
Adding a top defensive lineman did not really change much in that respect. What has to be done in the future is filling the spots that will be vacated when these players are no longer part of the picture.
They'll have plenty of cash to find many of those, but the draft will need to produce plenty. At least, the draft picks they'll have available after trading away two first-rounders and fourth-rounder will need to be good enough to fill those vacated spots.
Williams is going to command a ridiculous contract, but the key here is that salary cap is only going to keep increasing. That's all it ever does, except during the pandemic.
The other key is the Titans already took care of Bears problems adding talent because all of the years on Simmons' contract from 2027-30 total only $15.5 million in bonus money. In other words, Simmons' contract can act like a bank for the Bears to borrow from in future years when adding talent or getting under the cap.
It's always said the NFL salary cap is a myth. This certainly does not disprove that theory.
Caleb Williams counts 3.58% of the Bears' salary cap this year.
— Caleb Matas Pete (@CalebBears1) November 1, 2026
Next year it's 3.89%.
After that, the number changes forever (unless they get something done quicker).
This year he's at $10.8M and next year $12.6M, per Spotrac. That's why Chicago could afford to send out two…

Gene Chamberlain has covered the Chicago Bears full time as a beat writer since 1994 and prior to this on a part-time basis for 10 years. He covered the Bears as a beat writer for Suburban Chicago Newspapers, the Daily Southtown, Copley News Service and has been a contributor for the Daily Herald, the Associated Press, Bear Report, CBS Sports.com and The Sporting News. He also has worked a prep sports writer for Tribune Newspapers and Sun-Times newspapers.