NFL Preseason Week 3 kicks off tonight with Bears-Chiefs on NFL Network and Colts-Bengals on Prime Video (should you choose to watch another game during commercial breaks). But starting today, we — as a collective — need to keep our heads on a swivel because trade season is already underway.

The Chicago Bears (and the other 31 NFL teams) have until Tuesday at 3 p.m. CT to trim 90-player preseason rosters to 53. If you’re not good with math or don’t have a calculator on hand, that is a 37-player cut that will happen over the next 4-5 days. However, some teams won’t wait until after the cuts come down to bring in a player they really like. Hence, we’ll see teams come together on deals between now and cut-down time. Heck, it’s already started with the Cade York trade that we mentioned in Bullets and the intra-division deal between Washington and Philadelphia that sent receiver Jahan Dotson from the Commanders to the Eagles.

I don’t imagine it’ll be long before the Bears throw their hat in the ring and get in on some of these trade talks.

Chicago Bears trade rumors ahead of NFL cutdown day

In his weekly mailbag, Brad Biggs (Tribune) answers a question about a position group to keep an eye on around cut time. And while Biggs says that players who play edge rusher, offensive line, and return specialist roles are possible, there is an under-the-radar position to keep tabs on when it comes to potential Bears targets:

I imagine the Bears will be keeping a close eye on defensive tackles hitting the waiver wire or veterans who are cut and immediately become free agents. The Bears always could flip a late-round pick for a player if it’s someone they project as a rotational backup. … This just seems like a spot at which they could add a player and possibly one with a little experience.

A few things of note here via Biggsy…

Firstly, Biggs underscoring defensive tackle (and not end) as a position group that he sees the Bears possibly targeting with a late-summer trade is notable. Secondly, we shouldn’t overlook that Biggs notes the potential cost of doing business. Chicago’s football team owns four “late-round” picks. The team owns its own selections fifth and sixth rounds, as well as a sixth-rounder from the Steelers (which could become a fourth-rounder if Justin Fields plays 51 percent of the offensive snaps in Pittsburgh) and a sixth-round pick from the Dolphins (thanks to the Chase Claypool trade). Thirdly, I’m taking this Biggs anecdote as a sign that the team doesn’t totally love its depth along the interior of the defensive line.

Suddenly, my mind wants to focus on the defensive tackles tonight to see if anyone makes a big splash statement in the preseason finale.

It is no secret that the Bears have been looking for defensive line help throughout the offseason. To this point, the focus has been mostly at the edge/defensive end position. But once you get past Andrew Billings, Gervon Dexter Sr., and Zacch Pickens on the depth chart, the position group is littered with question marks. Do you feel confident in Byron Cowart, Michael Dwumfour, Keith Randolph Jr., Dashaun Mallory, or Jaylon Hutchings? If the Bears don’t, then I can see them aggressively exploring the trade market for help. Otherwise, they can wait out the waiver wire — where they have the No. 9 position.

Earlier this month, it was reported that Bears General Manager Ryan Poles was monitoring the market for offensive line help. I still believe that is the case. However, I wonder if O-line assistance has been bumped down the pecking order now that Nate Davis is healthy enough to participate in preseason action. Even still … I feel as if Poles would consider adding to the offensive line with the right player if the price is right.

During this week’s installment of HBO’s Hard Knocks, Poles made it clear that he is always on the lookout for options that will make his team better. Perhaps that obsessive mindset will net this team some help in the trenches via trade before NFL cuts start coming down. Stay tuned.