The Chicago Bears have already made one splashy move ahead of the 2026 NFL Trade Deadline.
So how about seconds?
Before piecing together this week’s post, I looked at what I did last week for inspiration. And hey, you can’t say we didn’t give you a heads up on the potential of a Jeffery Simmons trade:
The Bears just got a good look at Hooker and Simmons when they traveled to Nashville for joint practice sessions with the Titans. Perhaps that familiarity will help guide their search for a trade partner who can help upgrade their defensive line. Simmons is signed through 2030, so it might be more expensive to trade for him compared to players with expiring deals. But the juice could be worth the squeeze to reel in an impact defensive lineman whose future contract considerations seem reasonable.
Simmons is set to make his Bears debut on Monday Night Football. When he makes his home debut at Soldier Field, it will be on Sunday Night Football against the Tampa Bay Buccaneers in Week 9. Back-to-back primetime games for a guy who has spent the last few seasons on a rudderless Tennessee Titans team probably feels wild. But I digress.
After watching the Bears trade for Simmons, it is easy to wonder if this front office will make another move. After sorting through colleague Patrick Flowers’ 17 potential Bears trade targets post, here are some games to watch that will feature some possible trade fits.
Sep 20, 2026; Nashville, Tennessee, USA; Tennessee Titans defensive tackle Jeffery Simmons (98) takes the field during the first half against the Philadelphia Eagles at Nissan Stadium. Mandatory Credit: Steve Roberts-Imagn ImagesAfter the Jeffery Simmons Trade, Here Are the Week 8 Games to Watch For Bears Trade Fits
NFL GAMES AT NOON
These games are on CBS
Colts at Jaguars — Colts IDL Grover Stewart Titans at Bengals — Titans S Amani Hooker Browns at Steelers — Steelers EDGE Alex HighsmithEven though there is a case for the Bears to add another defensive lineman, I’m co-signing Patrick’s sentiment here:
Highsmith is a good player and has had a very good 2026 campaign. The Steelers are 5-2, so they’re not selling off assets for draft capital, especially with Aaron Rodgers playing out his final year. But Highsmith could be acquired in a trade that brings the Steelers a player at a position of need: wide receiver. I’m not seeing a fit here for the Bears, even if Chicago is an obvious name to attach to any defensive lineman.
The only reason I’m keeping Stewart on our list as a possible Bears trade fit is because it isn’t inconceivable that Chicago adds another interior defensive lineman if the price is right. Even if that happens, it would likely be a result of trade plans falling through elsewhere.
NOTE: The Ravens-Bills game will air on CBS-2 in Chicago. It doesn’t have any players on our watch list, but it should be a doozy of a game to watch if you want to put your peepers on some high-quality football.
These games are on FOX
Cardinals at Cowboys — Cardinals S Budda Baker, Cardinals EDGE Josh Sweat Raiders at Jets — Jets S Andre Cisco Falcons at Buccaneers — Bucs EDGE Yaya DiabyI made it clear which player I’d like to see the Bears target next via trade:
Showing up to your press conference in a full Halloween get-up is 10/10. No notes.[image or embed]
— Funky Cold Luda (@funkycoldluis.bsky.social) October 30, 2026 at 4:03 PMTHE LATE AFTERNOON SLATE
Chargers at Rams (FOX) — Chargers EDGE Khalil Mack Patriots at Dolphins (CBS) — Dolphins IDL Zach SielerThe Chargers-Rams game will not be shown on FOX locally in Chicago. Sorry to burst your bubble if you’re a Bears fan who was planning to do a Chargers Hate Watch on Sunday afternoon in hopes that it would knock some sense into a Chargers front office that reportedly refueses to engage in Khlail Mack trade discussions. Instead, the FOX single game on our plate will feature the Vikings and Lions. It’ll be a different kind of hate watch! Yay?
As for Sieler, I’d be surprised if the Bears went back to the interior. However, if they were to go back to the well, I can envision them targeting one on an expiring contract.
NOTE: The Chiefs-Broncos game will air on CBS-2 in Chicago. Again, it doesn’t have any players on our watch list. But it’ll be hard for me to not flip over to a game between two longtime AFC West foes. Nothing like a classic rivalry game for your Sunday viewing pleasure.
Oct 23, 2022; Inglewood, California, USA; Los Angeles Chargers linebacker Khalil Mack (52) celebrates after a touchdown in the first half against the Seattle Seahawks at SoFi Stadium. Mandatory Credit: Jayne Kamin-Oncea-USA TODAY SportsSUNDAY NIGHT FOOTBALL — EAGLES AT COMMANDERS
Eagles DL Moro Ojomo Eagles EDGE Nolan Smith Commanders EDGE Dorance Armstrong Jr.Only the NFL can get away with pitting a pair of teams with a combined record of 3-9-1 in primetime and not catch guff for it. The edge rushers here are worth monitoring. Smith is under contract for the rest of this season and will play next year on the fifth-year option. That might be appealing to a Bears front office that could value cost control. As for Armstrong, he is in the final year of his contract, which makes him a notable target. He doesn’t have any sacks this season, but Armstrong has collected 5+ sacks in each of the last five seasons.
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