The Potential Chicago Bears-Maxx Crosby Marriage, Revisited

Two weeks ago, I dropped 5 fake Maxx Crosby-to-Chicago deals. Maxx denies hearing trade talk from me (or from anybody, for that matter) so I'm re-dropping them, along with the social media backlash.

Feb 10, 2026

“ALL THE NOISE. IT’S NEWS TO ME.”

So said Las Vegas D-line menace Maxx Crosby, and to that, I call bullshit.

Generally speaking in the world of sports, where there’s smoke, there’s fire, and things have been eminently smoky around Crosby since the tail end of the 2025 NFL season, with credible reports claiming the 28-year-old defensive menace ain’t happy in Sin City.

Which means Bears fans are happy…or, more accurately, might be happy. Because if GM Ryan Poles can get Crosby to Chicago, things will get real for the Midway Monsters in 2026. And fast.

A couple weeks back, I put together a heap of fake trades that would land Crosby at Halas Hall, then followed up the article with a collection of the social media blowback. With Crosby claiming he’s clueless about the whole thing, I thought it would be appropriate — and hopefully fruitful — to revisit the fake trades and the attendant fallout.

To that end, if you have any cool Crosby-to-Chitown deal scenarios, fire ‘em off to ChicagoSportsStuff@gmail.com. I’ll print them up, and maybe it’ll help us get the dude in a Bears uni.

HOWZABOUT WE THROW AROUND some random numbers.

35 (26)
0 (24)
5.86% (22)
46.24 (26)
29% (28)

This looks like my 12-year-old daughter’s math homework — which, for what it’s worth, I couldn’t do, and neither could you. But no, this isn’t seventh-grade brain-teaser, but rather some of the 2025 Chicago Bears’ more notable, less impressive defensive stats:

Sacks: 35 (26th in the NFL)
EPA: 0 (24th)
Sack percentage 5.86% (22nd)
Success %: 46.24 (26th)
Passing Win Rate: 29% (28th)

Led by Montez Sweat, Grady Jarrett, Austin Booker, and a cast of dozens, the Bears’ line had its moments — in the second half of their Wild Card win over Green Bay, they drove Jordan Love to distraction, for instance — but for the most part, well, just look at the digits.

The 2026 Bears will be in the Super Bowl conversation next fall, but they could drive the convo if they shore up their pass rush, and few, if any would shore better than Las Vegas Raiders menace, Maxx Crosby.

With the right deal, the all-world 28-year-old D-lineman — who isn’t super-happy with the Raiders org — might be gettable, and if that’s indeed the case, Bears GM Ryan Poles should go out and get him while the getting’s good.

In 15 games this past season, Crosby racked up 10 sacks — almost 1/3rd of the Bears’ team total — the fourth time in his seven-year career he’s topped double digits. He also compiled a career-high 23.5 stuffs to go with 73 solo tackles and 28 assists. And, to reiterate, this was while missing two games.

Here are five semi-reasonable trade scenarios that might get one of the NFL’s current top-three lineman into Halas Hall.

TRADE #1: First-Rounders Galore

BEARS RECEIVE

Maxx Crosby

RAIDERS RECEIVE

Gervon Dexter Sr.
2026 first-round pick
2027 first-round pick

The talent-deficient Raiders would probably jump at this one, as the only way they’ll get back into Relevancy Land is via the draft. And the 24-year-old Dexter would slide right into their starting lineup. Yeah, Dex isn’t Crosby, but he’d be a decent consolation prize.

Before you’re all like, “Dude, giving up two firsts, WTF,” remember that the Bears are actually good, and those firsts will be near the bottom of the round. And you ain’t getting a Maxx Crosby at pick #22.

Why it works for the Bears

Crosby averaged between 75–80 pressures per season since 2021. Dexter didn’t.

Why it works for the Raiders

This one makes excellent financial sense, as Dexter’s cap hit would be in the $2 million range.

Realism Grade: B-

TRADE #2: No Sweat

BEARS RECEIVE

Maxx Crosby

RAIDERS RECEIVE

Montez Sweat
2026 first-round pick
2026 third-round pick
2027 second-round pick

Sweat has had his moments, but not so many that he’s untouchable. But he’s a bigger name than Dexter, which would appease the fan base, plus he still has a couple years left in his prime (he’s 29), so that might get it across the finish line.

Why it works for the Bears

Believe it or not, Sweat’s contract is less cost-effective than Crosby’s. Not one of Poles’ better decisions.

Why it works for the Raiders

Listen, Sweat may be overpaid, but he’s still a productive player. And it would be tough for Vegas to pass on three high-end picks.

Realism Grade: B

TRADE #3: Probably Won’t Happen, but Nice to Dream

BEARS RECEIVE

Maxx Crosby
2026 fourth-round pick

RAIDERS RECEIVE

Tyrique Stevenson
2026 first-round pick
2026 third-round pick

I’d love to get rid of Stevenson — he’s inconsistent and a bit of a knucklehead — but the Raiders need a defensive backfield, and Stevenson won’t merit a massive contract, and he’s only 25, so he could be appealing.

This feels like the Khalil Mack deal, which, while it didn’t lead to lengthy playoff runs, didn’t suck.

Why it works for the Bears

Stevenson is a good player, but I feel like he’s replaceable. I mean, Chicago lucked into Nahshon Wright, so there are likely upgrades to be found.

Why it works for the Raiders

This is my gut talking, but it strikes me that Stevenson could thrive in a new city. If the Raiders agree, this would be a fantastic get for them.

Realism Grade: C+

TRADE #4: Thanks, but No Thanks

BEARS RECEIVE

Maxx Crosby

RAIDERS RECEIVE

Darnell Wright
2026 second-round pick
2027 second-round pick
2028 third-round pick

Wright is about a season or two from becoming one of the NFL’s elite offensive linemen — some would argue that he already is elite — and elite linemen don’t grow on trees. On the plus side, Chicago wouldn’t lose a first (a first they could use to get Wright’s replacement), so if Poles really wants it to happen, this would be the way to go.

Why it works for the Bears

Last season, Poles landed Ozzy Trapillo in the second round, so he could probably get himself a day-one starter in the first round.

Why it works for the Raiders

The Raiders would jump at this one, and who could blame them? Wright’s a beast, and the Vegas O-line room is a beast-free zone.

Realism Grade: C-

TRADE #5: So Crazy it Just Might Work

BEARS RECEIVE

Maxx Crosby
2026 fifth-round pick

RAIDERS RECEIVE

Jaylon Johnson
2026 second-round pick
2027 third-round pick

Johnson is a top-shelf defender, but to get top-shelf, you generally have to give top-shelf.

Yes, it’d be tough to let Johnson go, but getting his contract off the books ($28 million-plus over the next two years) wouldn’t suck.

Why it works for the Bears

For a team in desperate need of a pass rush, re-allocating money from the D-backfield to the D-line is logical. Tough, but logical.

Why it works for the Raiders

Similar to the Trade #4, this gives the Raiders a high-end defender and a couple of solid day-two picks. This might be the best haul they’ll be able to get from the Bears…or anybody.

Realism Grade: A-