Roger Goodell and Robert Kraft don’t have a simple relationship. High-stakes meetings, Super Bowl trophies, and controversies have layered the relationship and strained both sides. Kraft has been one of the league’s most influential owners since the 1990s, and he helped bring Goodell into power in 2006. But then came Deflategate in 2015. It wasn’t just a scandal—it was a fracture.

The NFL went after Tom Brady aggressively, and Robert Kraft felt blindsided. A four-game suspension, a $1 million team fine, and the loss of first- and fourth-round draft picks followed. The tension between Kraft and Goodell was unmistakable. The air was cold. Kraft didn’t publicly withdraw his support for Goodell, but something had changed.

When Goodell returned to Gillette Stadium in 2017, the first game of the season, the ring ceremony in the rearview—it wasn’t just another night. The crowd knew. The optics mattered. Fans booed—loudly. Many in the crowd wore t-shirts with Goodell’s face, altered to include a red clown nose. The designer? None other than Dave Portnoy, a vocal critic of Goodell, and Kraft allowed it.

During the May 14 episode of the Club Shay Shay podcast, Kraft revealed: “We printed 40,000 towels with the little clown nose on them. A week before the game, I made a call to Patriots season ticket holders: ‘I need you to show up at this warehouse—I’m going to give you boxes, and you hand them out.’ Then the Krafts called me.” Surprised? You thought the owner would stop the Barstool founder from antics like that. Turns out, he helped make them happen.

In fact, he did the opposite. Portnoy added, “They’d heard about it and said, “You know we don’t let anything come into the stadium, and you’re not allowed to promote for free… but we’re just going to turn the other cheek on this. We’ll let these come in.” That moment took on a life of its own.” It’s hilarious. But his admission will make life difficult for the Patriots’ owner. They are already struggling now.

While the story will surely make the Pats’ owner uneasy, Portnoy has no problem. Even after the nose antics, his run-ins with the NFL commissioner have been plenty.

Roger Goodell has an insecure relationship with Dave Portnoy

The Barstool Sports owner revealed that the league doesn’t allow the Barstool reporters to come into the conferences of franchises, other than the Patriots. Now we know the reason. Portnoy once had secured a chance to meet the NFL commissioner in person. Alas, it failed in its initial stages.

Talking about the NFL supremo, Dave Portnoy said, “I’ve never met Roger, but he’s put me in cuffs twice.” He then revealed how Roger Goodell once organized a charity auction that went south. “During COVID, he did a charity auction where the winner could sit in his basement and watch Monday Night Football with him. I bid $250,000, won the auction, and then got an email saying NFL security did a background check and found I’d been arrested twice, so they wouldn’t allow it. But the only times I’ve ever been arrested were by them—that is the background check!” That’s interesting.

These interesting stories bring back the hot topic of Roger Goodell’s arrogance into discussion. The league owner doesn’t want to address his criticism. However, he prefers to be silent. The only plausible reason is that he doesn’t want any negative light on the NFL. He wants to spread only positive news around the league. But with rising criticism, how long will he stay quiet?