Let’s get this out of the way: the Bears are 4-2, and it still doesn’t totally make sense.
Ben Johnson has this squad playing like they didn’t get pantsed in Week 2. They’ve rattled off four straight, turned the offense into something resembling a real threat, and the defense? It’s been playing damn well — but the injury bug has sunk its teeth in hard. If Chicago’s serious about making a playoff run — and not just being the team that shows up and gets boat-raced on Wild Card weekend — they need reinforcements.
And no, not a depth linebacker or a third-string tight end. Real help. Strategic, plug-and-play dudes who can elevate this defense from “hanging on for dear life” to “giving teams hell in January.”
Here are three trade targets that make too much sense — one splash, one smart-as-hell rental, and one high-risk lottery ticket that could pay off huge.
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1. Trey Hendrickson, DE – Bengals
If the Bears want to growl instead of meow down the stretch, Hendrickson’s the move. Full stop.
The pass rush is garbage — we’re talking bottom-of-the-league, peewee flag-football levels of bad. Montez Sweat is doing what he can, but when he’s the only threat, offenses just slide protection and call it a day. That’s where Hendrickson comes in.
The guy led the league in sacks last year (17.5) and already has 4 more through six games in 2025. ESPN has him as the top trade value candidate at the deadline, and it’s not hard to see why. He’s a goddamn menace on third down, lives in the backfield, and would finally give the Bears the edge duo they’ve desperately needed.
Why it works:
- Immediate elite production (65 pressures last season!)
- Expiring contract = minimal long-term risk
- Bengals are 3-4 and might fold if they drop another game
What it costs:
A mid-round pick plus a young, cheap contributor. Think Ruben Hyppolite II and a 4th. If Poles is serious, he’ll pull the trigger.
Fit grade: A+
2. Alontae Taylor, CB – Saints
This is the sneaky move I actually expect to happen. With Jaylon Johnson on IR, Terell Smith out for the season, and Tyrique Stevenson banged up, the Bears are down to duct tape and prayer at corner.
Taylor’s not flashy, but he’s good. Versatile as hell, plays inside or outside, and already familiar with Dennis Allen’s scheme from their time in New Orleans. He’s having a quietly solid season: 34 tackles, 1 sack, 3 PBUs, and hasn’t given up a TD since Week 4.
He’s not a shutdown guy, but in this market? That’s gold.
Why it works:
- Can start immediately, fills glaring need
- On a cheap, expiring deal ($4.26M)
- Saints are 1-6 and definitely selling
What it costs:
A 5th-rounder, maybe a conditional 4th. Total Poles move.
Fit grade: A
3. Riq Woolen, CB – Seahawks
This one’s more of a moonshot.
Woolen’s having a down year. Like, really down — 41.1 PFF coverage grade, which is rough. But go back to 2022 and remember the rookie who looked like a damn alien out there? That guy is still in there somewhere.
Woolen is 6’4″, runs like a gazelle, and when he’s locked in, he’s a problem. Seattle’s defense has been solid overall, but if they’re looking to reshuffle, moving Woolen could make sense. Especially if they’ve soured on his development.
Why it works:
- Freak athlete with legit Pro Bowl ceiling
- Under contract through 2026
- Bears need young, moldable talent in the secondary
What it costs:
Probably a 3rd-rounder. Maybe less if Seattle’s desperate or secretly hates him.
Fit grade: B+ (with boom-or-bust potential)
Final Verdict
Look — the Bears aren’t just playing for relevance this year. They’re 4-2, trending up, and the NFC North is a f*ckin bloodbath. If Ryan Poles wants to make a move that says “we’re here to f*ck around and find out,” Hendrickson is that statement.
Taylor is the budget-friendly fix for an emergency corner situation. Woolen is the lottery ticket that could blow up in your face or turn into a long-term piece. Each of these guys solves a different problem, but all of them bring something the Bears don’t have right now: real upside.
The clock’s ticking. The trade deadline’s November 4. Let’s see if Poles has the stones to push this team over the top.
