Dave Portnoy speaks out to Megyn Kelly on Bill Belichick debacle: ‘The age gap is huge’

If anyone is an expert on questionable age gap relationships, it’s Barstool Sports founder Dave Portnoy.

Not so long ago, Portnoy was on the receiving end of a media firestorm due to his relationship with a women half his age (she was 20, he was 43). The relationship in question was part of an explosive Business Insider article on Portnoy’s sex and dating life and alleged the Barstool founder recorded sexual encounters without consent, among many other lurid accusations. Portnoy denied the allegations and would go on to sue Business Insider for the article, with the suit later dismissed.

Now, Portnoy is discussing the bizarre relationship of former New England Patriots coach Bill Belichick, whose girlfriend, Jordon Hudson, is nearly 50-years his younger. The couple has been in the headlines all week after Hudson, who seemingly has substantial influence over Belichick’s media appearances, interrupted an interview with CBS Sunday Morning after anchor Tony Dokoupil asked a question about how the two met.

Surprisingly, Portnoy, a lifelong Patriots fan who now considers Belichick a peer as both live in Nantucket, did not rush to the legendary coach’s defense during an appearance on Megyn Kelly’s radio show Thursday.

.@stoolpresidente on Bill Belichick’s relationship: “It’s just a very awkward situation. The age gap is huge, clearly, but she runs the show. There’s rumors… ‘Hard Knocks’ for HBO was supposed to do North Carolina, she shut that down… It’s such a juxtaposition of a guy who… pic.twitter.com/BTWEbgv1lc

— The Megyn Kelly Show (@MegynKellyShow) May 1, 2025

“I’ll start by saying I am a diehard New England Patriots fan. Diehard. I love Bill Belichick, he’s like my guy, he’s brought so many championships. I know him personally. He lives on Nantucket, I live on Nantucket. I’ve met Jordon, so it’s a very awkward thing to see,” Portnoy began.

“I was squirming,” he said of the CBS interview. “I don’t know what to expect. I don’t know what to think about it. It certainly was awkward. I’ve heard people say, you know, ‘Is she taking advantage of him?’ Well, he’s taking advantage of her. He’s sleeping with a very attractive young girl, 50 years younger.

“I don’t know why she’s so involved. Like, I really don’t. I’ve met her, she’s nice enough. She’s running the whole show, I’ve known that a couple months ago. Like she, every piece of Bill Belichick business goes through her. Like, she is basically- she would act, like, if that was maybe not in a romantic relationship, and that’s his PR manager, nobody’s blinking at that. Like, that happens, I’m sure, a lot with celebs that are not gonna talk about it,” the Barstool founder said of Hudson’s interruption.

“Now, you combine it with Bill Belichick who is gruff with the media and generally always handles himself, it’s just a very awkward situation. The age gap is huge, clearly, but she runs the show. There’s rumors Hard Knocks, for HBO, was supposed to do North Carolina, she shut that down. …It’s such a juxtaposition of a guy who seemingly had no media savvy, but was always just straightforward, no time for the media, now having his life run by a 25-year old. It certainly is eye-opening for a guy like me.”

Eye-opening is… one way to put it given Portnoy’s history. But his comments are certainly notable independent of that. Outside of maybe Bill Simmons, Dave Portnoy is the biggest Belichick cheerleader in sports media. The fact that he’d call out the six-time Super Bowl-winning head coach for letting Hudson “run his life,” especially if he had knowledge of the dynamic months ago, means that this is a real story outside of the one incident on CBS.

It seems like Belichick has lost the room, even among his most ardent supporters. The question now is whether or not he can keep his Tar Heel locker room in order with all of the noise off the field.