Earlier today we dropped the first part of this roundtable discussion between myself and a few others here at Windy City Gridiron. Now we get into whether or not we feel that the Chicago Bears will indeed make a move, and what some of the likeliest deals are to be made elsewhere. A trade market I expect to explode long before the annual trade deadline of week six.
Question 3) Do you think the Bears will make a trade after the date of June 1st? Why or why not?
Gary Baugher Jr: Yes, but I don’t believe it be anything major, depth move for a late round pick or something at the most. I think we’ve
had enough clear indication that the roster is mostly in a spot the team likes, all though if we made a splash for an Edge I would never complain…
Josh Sunderbruch: Probably? Ryan Poles likes to fiddle and tinker with things, and it seems like he might decide to do something random to bring in a guy who might or might not actually play meaningful reps.
Donald Gooch: Not really. I think the Bears have accepted that they’re constrained by their contract commitments, and they have a lot of confidence in the changes they’ve already made to get more of a DA defense on the field in 2026. I think they are content to wait until 2027 to remake the defensive line. And I think they are betting on a Booker breakout.
Myself: Yes. I do believe it won’t be immediately after June 1st comes and goes, but the Bears have been way too involved with looking at options in the veteran defensive end market to not make a deal happen. General manager Ryan Poles has a history of making trades happen when people least expect anything to happen. Once he lands a player on a deal with a price he’s comfortable with paying, he will make his move. Whomever that might be.
Question 4) Besides AJ Brown to the Patriots what move do you expect to see made elsewhere in the league?
Gary Baugher Jr: I gotta go back to Josh Sweat once more, already requested a trade and the team is fielding calls for him, he seems to be the most likely big name on the move post June 1st.
Josh Sunderbruch: I anticipate the Texans doing something baffling, probably with their offensive line. Some desperate GM is going to give up too much for a mid wide receiver or defensive tackle.
Author’s note – Josh simply wins here with an absolute burner of a take on what has been a squirrely roster-building process in Houston.
Donald Gooch: Outside of the aforementioned Josh Sweat, I think that both Kavon Thibodeaux and Brandon Aiuk will be playing for different teams in 2026. I do not expect a Cole Kmet trade, and frankly, I find those trade rumors a bit silly. Anthony Richardson might find a new home for a late-round pick.
Myself: I previously said I do not want to see the Bears entertain any offers for Alvin Kamara. That remains true; however, I fully expect the veteran do-it-all back to be shipped off elsewhere within the next two weeks. The Saints have been very coy about his status, and frankly, I think it’s just extensive salesmanship at this point. I also think at least one big fish of an EDGE player gets auctioned off elsewhere.
What about you guys and gals? What do y’all believe will happen once June 1st rolls into June 2nd?
