Saturday, October 24, 2026
EDGE is live. Chicago fans can now access and explore the beta.

Bears Players Roasted Caleb Williams Hater Dave Portnoy After Beating His Patriots

-

Anyone familiar with the modern sports media landscape has heard of Barstool. It was founded by Dave Portnoy as a sort of sports enterprise by the fans, for the fans. It’s certainly had plenty of success, but hasn’t done much for the image of its owner. Over the years, Portnoy has earned a reputation less as a happy-go-lucky fan living the American dream and more as an ignorant blowhard who likes to hear himself talk. Never is that clearer than any time he’s talking about Caleb Williams.

Portnoy has been outspoken about the Chicago Bears’ quarterback for years. He has stated on more than one occasion that he believed Williams was destined to be a bust coming out of USC. He’s also offered not-so-subtle hints that Williams is soft, a crybaby, and not a real man. That was on display a few weeks ago when he called out the quarterback for milking his “minor” hamstring injury.

Well, it seems Bears players didn’t take kindly to those remarks. After beating the New England Patriots, Portnoy’s favorite team, on Thursday Night Football, cornerback Kyler Gordon and tight end Colston Loveland decided to send him a message.

Dave Portnoy built a side gig as a pizza reviewer.

He’d go to various places with a strong reputation and review their pies. He’d then give them a rating. Plenty of restaurants weren’t happy about it, feeling he was using his platform to stain their reputations. What makes him the end-all be-all of pizza experts? The guy was a degenerate gambler who failed at his first career as a market researcher before hitting it big with Barstool Sports. Even that didn’t become a success until he started including beautiful women in his newspaper and blog.

🔥 Subscribe to the Untold Chicago YouTube channel to hear Chicago legends tell stories you’ve never seen in headlines — real moments, real experiences, straight from the athletes themselves.

Everything about the guy screams sleaze. He did not play sports at any meaningful level in his life, yet he acts like he has a clear eye for who the good players are. Keep in mind, one of his primary motivations was rejecting political correctness. So, of course, he disliked Williams. The Bears quarterback is very much a modern-day athlete who rejects the gruff, tough-guy persona. He loves fashion. He paints his nails for fun. It is anathema to everything Dave Portnoy stands for.

Williams doesn’t have to worry about it.

He clearly has the firm backing of his teammates, who seem to dislike Portnoy as much as pretty much everybody. Beating the Patriots was fun on its own. Knowing they also ruined his week was icing on the cake. One has to imagine Williams’ excellent performance in that game was partially motivated by what Portnoy said about him weeks ago. The Bears quarterback is exactly the type of person who’d file that away until he needed it. Beating New England’s golden boy, Drake Maye, only added to the thrill.

Rest assured, this isn’t likely to shut Portnoy up. He’ll run his mouth regardless. That suits the Bears fine. They don’t mind firing right back. One must applaud them for saving their shot for when it would sting the most. Portnoy would be wise not to do any pizza reviews in Chicago anytime soon. He might not make it out of town alive.

Erik Lambert
Erik Lambert
I’m a football writer with more than 15 years covering the Chicago Bears. I hold a master’s degree in the Teaching of Writing from Columbia College Chicago, and my work on Sports Mockery has earned more than twenty million views. I focus on providing analysis, context, and reporting on Bears strategy, roster decisions, and team developments, and I’ve shared insight on 670 The Score, ESPN 1000, and football podcasts in the U.S. and Europe.

Chicago SportsNEWS
Recommended for you

← More Chicago Bears News & Rumors | SportsMockery Home