There are few bigger trolls on the internet than Barstool Sports founder Dave Portnoy, so it was funny to see him get a taste of his own medicine from Caleb Williams, Colston Loveland and Kyler Gordon.

Portnoy had a lot to say about Williams after he went down with a hamstring injury in Week 2 before it was later discovered that the Bears quarterback had a more serious issue than initially thought.

Rest assured, Williams saw Portnoy mocking him, so he took the opportunity to troll Portnoy after the Bears beat his favorite team, the New England Patriots, in Week 7.

Caleb Williams trolls Dave Portnoy

On Instagram, Williams reposted a social media post of Portnoy's that included a photo of a handful of Barstool analysts picking the Bears to beat the Patriots. Portnoy had also included several eye emojis.

"On to the next," Williams wrote in the caption of the post.

Portnoy later responded.

FETISH ALERT 🚨 See you in Feb @CALEBcsw pic.twitter.com/lRIzAFfT9n

— Dave Portnoy (@stoolpresidente) October 23, 2026

It's pretty comical that Portnoy would accuse Williams of having a fetish considering he takes every chance he gets to knock Williams, but I digress

Of course, this isn't the first time Portnoy and Williams have had a back-and-forth.

As we mentioned, Portnoy mocked Williams after his hamstring injury, as did the rest of the internet, and Williams later fired back at him with a repost on social media that basically accused Portnoy of being soft.

Portnoy then knocked Williams for not divulging more about his injury when Williams first addressed the media during the week the Bears quarterback returned to the field.

Loveland, Gordon troll Portnoy

Bears players weren't done there.

Gordon and Loveland did a pizza review after the game, which was a clear troll of Portnoy and the countless pizza reviews he has done over the years.

It was pretty well done, except they forgot the score.

Bears players Kyler Gordon and Colston Loveland dropped a pizza review after last night’s win

We cannot confirm or deny if they were trolling any Patriots fans that do pizza reviews pic.twitter.com/6Og9saWd8Q

— Barstool Sports (@barstoolsports) October 23, 2026

A break from the norm

The Bears have struggled mightily to beat the Patriots over the years, and that was the case for a lot of teams during the Tom Brady era.

Before their win on Thursday night, the Bears had lost six of their last seven against New England, with the last win coming in 2022.

However, with that win and the one in Week 7, the Bears are starting to flip the script and have now won two of three.

Barring a meeting in the Super Bowl, this will be the last time these two teams square off until at least 2028, as New England is not on Chicago's schedule next season.

In 2028, the Bears are slated to face one AFC East opponent, but who that is will depend upon where the Bears finish in the division.