What the Chicago Bears should do to help Caleb Williams succeed: 7 bold moves

If the Bears hope to be relevant in 2025 and beyond, they’ll need to swing for the fences.
Caleb Williams dreaming of year two
Caleb Williams dreaming of year two / Jeffrey Becker-Imagn Images
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The Chicago Bears aren’t the kind of franchise that goes for it. Like rather than draft a player with a few red flags (Jalen Carter), they’ll grab an uninspiring option (Darnell Wright.)

Because, safety.

Playing it safe is fine if your franchise has a history of making safety work. The Bears, however, aren’t working, so it’s time to get bold—especially when the team’s number one goal is unlock Caleb Williams’ considerable potential.

It’s possible GM Ryan Poles is aware that if the Bears have a repeat of 2024, he could be filing for unemployment next January, so maybe he’d be willing to throw caution to the wind. If that is the case, here’s we should see from the Bears between now and training camp:

Give the Running Back a Makeover

Drafting Ashton Jeanty and/or signing Najee Harris would both improve the team’s 25th-ranked rushing attack and give Caleb some much-needed support. Keeping D’Andre Swift as the lead rusher won’t.

Trade Their Two Second Round Picks For a First Rounder

The Bears have holes galore, but Poles could decide that shipping picks #39 and #41 to, say, Dallas for #12 might simultaneously help Caleb and speed the rebuild. (And yes, they’re rebuilding.)

Let Keenan Allen Walk

Admittedly, this’ll be a bummer for Williams—Allen was targeted 121 times, a number that would’ve been higher had Allen not missed a couple of games—but there are plenty of free agent WR’s who would be useful, among them…

Overpay Tee Higgins

Williams himself will be decamped on Higgins’ doorstep the second the legal tampering period ends, a four-year, $86 million contract in hand. Would you blame him?

Say Goodbye to Cole Kmet

It’s possible that the tight end’s meh 2024 was due to a shoddy offensive scheme. But it’s also possible that he’s simply a meh tight end. Williams doesn’t need a meh tight end.

Move on from Teven Jenkins

Addition by subtraction. Jenkins is an injury waiting to happen—he hasn’t played a full 17-game season in his four-year career—and letting him walk will allow the Bears to bring back an old friend, that being…

Sign James Daniel

It seems like Daniel’s been in the league for 52 years, but the fact is he’s only 27 and he was PFF’s second-highest graded tackle in 2024. If the Bears are willing to pony up the ducats, this would be a win for everybody—especially Caleb Williams.


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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.