Caleb Williams stands on the sideline holding his collar
Caleb Williams #18 of the Chicago Bears stands on the sideline during the national anthem prior to the game against the Minnesota Vikings at Soldier Field on September 20, 2026 in Chicago, Illinois. | Todd Rosenberg/Getty Images
Every football fan in Chicago held their collective breath on Sunday when Bears quarterback Caleb Williams crumpled to the ground in mid-run after suffering what looked like a major leg injury in an NFL game.
Eventually, the Bears medical staff carted their franchise quarterback off the field with a towel draped around his head as Williams gave vent to his emotions. When he gestured to a cheering Soldier Field crowd, everyone could see that he had been crying.
It was a heartbreaking scene and everyone who watched it dreaded what this could mean for his future.
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So after the Bears announced that Williams’ injury wasn’t as bad as feared and listed his status as “week-to-week,” what did certain luminaries in the football manosphere choose to discuss?
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Williams’ painted nails. His crying.
And by association, his perceived softness.
Homophobes love to attack Caleb Williams and his nails
Barstool Sports founder Dave Portnoy took a break from defending himself against a cancel culture mob that doesn’t exist to offer a take on Williams’ injury that no one asked for.
During an appearance on FS1’s “Wake Up Barstool,” Portnoy offered his signature blend of humor-free joke-like objects delivered with the charisma of a sixth grade boy reading baldness pill legal copy.
“The man tweaked his hammy, and acted like both ACLs, MCLs, and everything else had been torn…”
–@stoolpresidente has given Caleb Williams a new nickname; “The Thespian” pic.twitter.com/SDguE8jLPo
— Wake Up Barstool (@wakeupbarstool) September 21, 2026
“Who knows what’s going on with ‘The Thesbian?’” Portnoy made sure to pronounced “thespian” as if rhymed with “lesbian.”
Portnoy asked as the show’s co-hosts audibly chortled long enough to ensure that their checks cleared, “You know…’Inside the Actor’s Studio.’ You don’t know what his injury’s gonna be…The man tweaked his hammy and acted like both ACLs, MCLs, and everything else he had…He tweaked his hammy! What are we doing here?!”
Get it? Since Williams’ injury wasn’t as bad as it first appeared, that apparently made him Chappell Roan.
Which, come to think of it, would be amazing. No wonder 100 thousand Chicagoans cheer his every move.
OutKick and Barstool in a constant battle for last place
Despite Portnoy’s usual ignorance, though, OutKick somehow topped the Barstool founder for the worst response to the Williams injury and its aftermath.
That was courtesy of OutKick podcast host Craig Carton.
Caleb Williams’ reaction to a first-degree hamstring strain is exactly why he may never truly resonate with Bears fans
"He acted like his career ended" pic.twitter.com/B3DX8xs9Qf
— The Craig Carton Show (@CraigCartonShow) September 21, 2026
Sounding like what would happen if Shaggy from Scooby Doo called in to Fox and Friends, Carton bleated, “The problem that Caleb Williams suffered, despite it looking like a serious career ending season-ended injury, is that he merely has…vaginitis.”
Somewhere on the far reaches of the universe, there exists a black hole that swallows up all sound and emits nothing but what NASA describes as “a low-pitched groaning.” That is exactly what this joke deserves.
After invoking famous macho Bears men’s men of the past like Mike Ditka and Brian Urlacher, Carton hit on what he felt was at the heart of Williams’ response to his injury.
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“When you act like that, when you’re not hurt that badly, it brings a lot of dudes back to ‘I never trusted him when he painted his fingernails pink!’” he ranted.
Carton further added, “And that’s the problem. Caleb Williams is, I think, gonna be a damn good quarterback for a long time. But he’s never really truly gonna resonate with a Bears football fan. ‘Cause he’s never gonna be one of you.”
There it was. A New York sports radio host whose entire concept of Bears fans appeared to originate from a three-decade old SNL Superfans sketch presumed to speak for Chicago and told us that Williams is “never gonna be one of you” because he paints his nails.
You know…those same painted nails that led one of greatest comeback victories in franchise history over the hated Packers during last season’s NFL playoffs.
In that game’s wake, it sure looked like Chicago accepted Williams as one of its own.
Self-appointed guardians of heterosexual manliness and their weird online followers can heave every attack they can think of at Williams for crying because he thought his season was over.
If his next ride is on top of a Michigan Avenue bus during a Bears Super Bowl parade, he will become the face—and painted nails—of Chicago.
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