Tom Brady has never been a stranger to high-end fashion. He has walked a few Met Gala red carpets. But recently, he turned heads by modeling for Demna at Gucci’s Times Square show in sleek black leather pants and a matching jacket. He pushed the boundaries even further in front of GQ’s lenses, posing in an edgy, open-chest gray suit. While the fashion world celebrated the seven-time Super Bowl champion’s bold aesthetic, Dave Portnoy stood as a critic. 

“Look how they massacred my boy!” Portnoy wrote as he shared Brady’s picture in the gray suit on his Instagram Story. 

But the Barstool co-founder didn’t stop there. He sent another reaction response on X, replying to GQ’s post featuring Brady in the two aforementioned outfits. 

“BLINK TWICE IF YOU NEED HELP TOMMY!” Portnoy humorously remarked.

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This isn’t the first time Portnoy has voiced disappointment over Brady’s post-retirement choices. He slammed the former quarterback after he slapped Logan Paul at the Fanatics Fest. Portnoy questioned Brady’s brand trajectory and claimed that his legacy was being “lame-ified.” The unconventional appearances and acts made him believe that Brady’s post-retirement image was “one of the great downfalls of an icon.”

However, plenty of heavyweights rushed to Brady’s defense. And former NBA superstar Shaquille O’Neal was one of them. Firing back at Portnoy’s criticism, ‘Big Shaq’ said: “I’d be glad if somebody punches him in the face. And I hope it’s Tom [Brady]”.

Portnoy previously ripped Brady’s broadcasting skills. And even before that, Portnoy claimed that the quarterback received $75 million to participate in a flag football showcase in Saudi Arabia. But Brady quickly shut him down and called Portnoy out for false reporting, asking whether people were “picking numbers out of a hat.”

Despite the internet jokes, Brady’s foray into high fashion is only picking up momentum. The NFL legend is set to appear in an upcoming Fall/Winter 2026 campaign shot by renowned photographer Michal Chelbin. But he won’t be alone. This time, Alex Consani, EsDeeKid, and Shawn Mendes will join him.

Owing to his recent inclination towards fashion, GQ asked if Brady would appear in more high-fashion campaigns in the future. And Brady was ready to step out of his comfort zone. 

“I would never say never to doing anything, so if there was an opportunity that presented itself that I thought was really fun and new, I would definitely be open to it,” the 49-year-old said. “I always say the only place for growth is outside your comfort zone, and I think this was one of those things: doing something that I had never really done on a big stage with some really great people.” 

Brady spent more than two decades dominating the NFL by ignoring outside noise. And his post-retirement modeling career appears to be following a similar playbook. Of course, die-hard football traditionalists like Portnoy might cringe at shirtless runway suits. But for Brady, it’s simply another world to conquer.