Bear Digest

A new weapon for Caleb Williams: 4 deals that will get Cooper Kupp on the Chicago Bears immediately

Is Rams wide receiver Cooper Kupp sprinting to Chicago?
Is Rams wide receiver Cooper Kupp sprinting to Chicago? | Bill Streicher-Imagn Images

In this story:


After a mostly wonderful career in Los Angeles, the Rams are kicking Cooper Kupp to the curb. And the wide receiver ain’t happy about it.

The kindest part of the announcement is that the Rams are, “…working with [Kupp] and [his] family to find the right place to continue competing for championships.”

Should that place be Chicago?

Yes. Please. Thank you. And here are four ways that Bears GM Ryan Poles can make it happen.

Trade #1

CHICAGO RECEIVES

  • Cooper Kupp

LOS ANGELES RAMS RECEIVE

  • 2025 third round pick
  • 2026 fifth round pick

This would be the least complex way to get Kupp into the building: A couple of picks, done, call it a day.

Would L.A. go for it? There’s plenty of wide receiver value to be had in round three, some recent examples being Chris Godwin, Keenan Allen, Tyler Lockett, and—wait for it, wait for it—Cooper Kupp.

Trade #2

CHICAGO RECEIVES

  • Cooper Kupp

LOS ANGELES RAMS RECEIVE

  • Tyrique Stevenson
  • 2025 fifth round pick

A huge contingent of Bears fans—this writer among them—would love to see Stevenson shipped out of town, as we still hold a grudge for his super-foolish behavior that led to the infamous Hail Jayden disaster.

The Rams need some help in the defensive backfield, and if L.A. coach Sean McVey can knock some sense into Stevenson, it’s a win/win.

Trade #3

CHICAGO RECEIVES

  • Cooper Kupp
  • Los Angeles 2025 second round pick

LOS ANGELES RAMS RECEIVE

  • Kyler Gordon
  • Chicago 2025 fifth round pick

Gordon is beloved inside of Halas Hall, but landing Kupp and a second would be hard for Poles to turn down.

Trade #4

CHICAGO RECEIVES

  • Cooper Kupp

LOS ANGEES RECEIVES

  • D’Andre Swift
  • Chicago 2025 sixth round pick

Two words: Domino effect. This move would make it a whole lot easier for Poles to draft Ashton Jeanty or sign free agent Aaron Jones Jr.—either of which would thrill this writer to no end.

Okay, it’s just two dominoes, but those two dominoes could help Caleb Williams drag the Bears to the 2025 playoffs.


Published | Modified
Alan Goldsher
ALAN GOLDSHER

Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.

Share on XFollow AlanGoldsher