Credit: Wake Up Barstool; Kirby Lee – Imagn Images

Ever since Tom Brady reemerged in the public eye around 2024, he has had a complicated relationship with the New England Patriots.

Despite leading the franchise to six Super Bowl trophies, Brady has not been as warm toward the Patriots and their fans as one might expect. Even a statue at Gillette Stadium was not enough to solidify Brady’s tightness with the team.

Just in the last few months, the NFL on Fox analyst stated he did not “have a dog in the fight” in Super Bowl LX, as the Patriots competed for championship No. 7. Brady also vied for Los Angeles Rams QB Matt Stafford to win the MVP award over Patriots sophomore star Drake Maye.

The latest wrinkle in the saga came this week, as reports surfaced that Brady intervened to prevent New England from acquiring outgoing Raiders edge rusher Maxx Crosby, who was eventually traded to Baltimore.

It was the final straw for Barstool boss Dave Portnoy, a notorious Patriots fanatic. On Monday’s episode of Wake Up Barstool on FS1, Portnoy made a big show of cutting ties with the Patriots legend.

But more interestingly, Portnoy also offered a theory that he believes could explain why Brady has a vendetta against the team.

“I have a theory on what this all stems from. Because from the outside it makes no sense, right?” Portnoy said.

“(Bill) Belichick gone. He’s friends with (Robert) Kraft. (Mike) Vrabel, he played with. So what is this hatred of the New England Patriots? The only thing I can think is he wanted to buy into the Patriots, and he wanted it basically for free like he got from the Raiders, and it didn’t happen, and he’s holding a grudge. Nothing else makes sense to me.”

Brady purchased a minority stake in the Las Vegas Raiders in late 2023, at what has been widely stated was a steep discount. The Washington Post reported Brady bought between 5 and 10 percent of the team at as much as a 70 percent discount. NFL owners delayed approval of Brady’s purchase for about a year due to reported frustration with the deal.

No talks between Brady and the Patriots have been reported, but it stands to reason that Brady would have explored such a deal before moving on to the Raiders. It also stands to reason that the notoriously cash-poor Raiders would be far more likely to give Brady a cupcake deal than the Krafts.

Either way, Portnoy is out on Brady.

“It’s just one thing after another to the point (where) if you’re a Patriots fan, you can come to no other conclusion than he hates the New England Patriots,” he said.

“It’s not an accident. We just put a statue of the guy, I say, tear it down. Thank you for your Super Bowls. You’re just a guy. Go play in your flag football game, go be in a million ads. But I don’t need you in my life anymore, and you don’t need us.”

About Brendon Kleen

Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.