Hello, Chicago Bears Fans! For this hypothetical scenario on the Chicago Bears’ offseason plans, I tried to envision what it would look like if the Bears tried to fix the defensive line just as they did the interior of the offensive line last season. So the basic outline of the scenario is this: 1) a big splash free agent signing at either the DT or DE positions, much like the Drew Dalman signing last season, 2) a significant trade where I send draft capital for a former Pro Bowl or All Pro player
who is getting on in years, but still playing at a high level, and where the trading team could stand to clear some cap space, like the Joe Thuney trade with Kansas City, giving up a 4th round pick, and 3) a lower tier trade where I bet on upside on a player who was either injured or underperformed last season, like the trade for Jonah Jackson from the LA Rams that netted the Rams a 6th round pick.
So before I made these moves, I restructured some contracts: Montez Sweat, DJ Moore, and Jaylon Johnson – converting their base salaries to signing bonuses and spreading the hits – in Sweat’s case, I added a void year. I cut Edmunds, netting $15 million against $2.4 million dead cap and D’Andre Swift, as a post-June cut, saving $7 million.
Projected 2026 cap space created: $72 million dollars.
Step One: Big Splash Free Agent Signing: Bears sign Trey Hendrickson 3 years, $99 million ($33M AAV)
At 31, Hendrickson is coming off core muscle surgery in his hip/pelvis area and a lost 2025 season, where he played in only seven games and dropped to 4 sacks, after posting back-to-back seasons where he led the league in sacks. I bet big here on Hendrickson returning to form and at least giving me two seasons near his peak performance. His elite first-step quickness, familiarity with Dennis Allen and his scheme, and relentless motor are just too good to pass up. Like Dalman at the center position in the 2025 free agency period, he’s the perfect fit at a major area of need for the Chicago Bears. I guarantee $50 million of the contract with a bit of front loading to manage the contract hit in the final season.
Step Two: Long in the Tooth but Still Killing it Trade Acquisition: Chris Jones, DT/DE Kansas City Chiefs for 2026 Third Round Pick
Here I go back to the team that gifted us Joe Thuney last year. While Kansas City restructured Patrick Mahomes’ contract to create $43 million in cap space, they are still $11 million over with a number of free agents and pending free agents to account for. While Jones remains an All-Pro caliber interior disruptor at age 32, just like Thuney, he is rapidly approaching his decline phase. KC is coming off of a disastrous 2025 season, and they do not know when they will have Patrick Mahomes back under center in 2026. Chris Jones is under contract with Kansas City through 2028. In this trade, I give up our third round pick (age / contract value = less draft compensation for KC) and give Jones a small contract extension through 2030, his age 36 season (fully expecting to cut him that year), in order to fit him under our cap. As part of the extension I restructure, converting his $19 million base to bonus and dropping his 2026 cap hit. With the Bears undoubtedly cutting Grady Jarrett next season, and either cutting Dayo or coming to an injury settlement with him, I can absorb Jones’ contract in 2027 going forward.
Step Three: Lower-Tier Trade Betting on Upside – Bears trade for DaRon Payne, DT Washington Commanders for 1st of two 7th round picks in 2026 Draft
DaRon Payne was once one of the best defensive tackles in the NFL, and there were rumors swirling that the Chicago Bears were interested in acquiring him just a few years ago. Instead, the Commanders signed Payne to a big extension and traded Montez Sweat to the Bears for a second-round pick. That choice has not worked out for the Commanders, as Payne’s play has significantly declined the last two years. Still, he had 46 tackles, three sacks, and one forced fumble in a lost season for the Commanders in 2025. He remains a decent run-stuffing tackle at age 29, and is a viable replacement for Andrew Billings, who is expected to leave the Bears in free agency.
DaRon Payne is entering the final season of the 4-year $90 million contract he signed with the Commanders, and carries with him a $27.95 million cap hit. He is a cut candidate for the Commanders, but instead, they do a small trade with the Chicago Bears, netting the first of the two 7th round picks the Bears hold in the 2026 NFL draft. As part of the trade I extend Payne with a two year extension with a void year, and add some sack incentives to motivate the big man. Payne is no longer a star, but perhaps he can regain a bit of that magic he had, rejoining with his former Commanders teammate in Sweat, and help the Bears’ interior run defense, which was one of the worst run defenses in the entire NFL in 2025.
So what do you think, Chicago Bears fans? This plan definitely ages up our defensive line, adding a 31 year old, a 32 year old, and a 29 year old to a defensive line that already has some older players in Sweat and Jarrett. This would in no way change my focus on defensive end and defensive tackle in the NFL draft this season, as most of these players would be gone by the 2028-2029 season. Still, consider the impact this defensive line could have for the Chicago Bears in the 2026-2027 NFL season:
Left Defensive End: Montez Sweat, Daniel Hardy
Interior Defensive Line: Chris Jones, DaRon Payne, Gervon Dexter, Grady Jarrett, Shemar Turner
Right Defensive End: Trey Hendrickson, Austin Booker
That works for me. But tell us how you would try to match the Chicago Bears’ interior offensive line offseason in 2025 with a 2026 offseason for the Bears’ defensive line in the comments!
