“I Was Squirming In My Seat”: Dave Portnoy Reveals His Shocking Take On Bill Belichick “Being Held Hostage” By His 24-Year-Old Girlfriend Jordon Hudson

Barstool Sports owner and founder Dave Portnoy revealed his shocking reaction to the Bill Belichick-Jordon Hudson interview fiasco with CBS.

Bill Belichick spoke with Tony Dokoupil on the popular CBS “Sunday Morning” show to discuss his new book, The Art of Winning: Lessons from My Life in Football. The interview, however, quickly turned awkward when Jordon Hudson stepped in to shut down a question about their relationship.

Belichick’s relationship with Hudson has drawn immense media coverage, due to their 49-year age gap (Belichick is 73, Hudson 24). Dokoupil asked Belichick how they met, prompting Hudson to interrupt and state that they weren’t discussing the topic:

"We're not talking about this."

Jordon Hudson interrupts Bill Belichick's CBS Sunday interview when he's asked how they met 😳 pic.twitter.com/LvncZ88UVY

— Complex Sports (@ComplexSports) April 27, 2025

Speaking on the latest episode of the “Barstool Rundown” podcast, Portnoy offered his take on the strange interview with Bill Belichick and Jordon Hudson that has made headlines across the football world:

“Imagine my surprise this morning when they had the most awkward Bill Belichick interview I’ve ever seen. I was squirming in my seat…I don’t know if he knew anyone else saw those (Halloween) photos. I was literally squirming. Then it went crazy viral. People are saying he’s like being held hostage. I don’t think he knows still what social media is and that these photos are out there…

He’s been a guy who’s never cared what anybody has thought. But I’ve never seen him seemingly stunned in an interview…I’ve just never seen it. For it to come from the ‘CBS Sunday Morning’ guy…these are the nicest interviewers ever.”

Bill Belichick was always private about his personal life during his tenure as head coach of the New England Patriots. And of course, he was a man of very few words when he spoke to the media.

But Hudson has posted about their relationship aplenty on her Instagram account, and leaked emails showed Belichick asking staffers at North Carolina to CC his girlfriend on certain emails.

Before his relationship with Hudson, Belichick had a 16-year romance with Linda Holliday. He was previously married to Debby Clarke for 29 years, and they had three children together.

Bill Belichick Begins New Era On Chapel Hill

Less than a year after his departure from the Patriots, Belichick signed a five-year deal to take over as the head football coach of the Tar Heels in December worth a whopping $50 million.

Belichick was employed as an NFL coach every year from 1975 to 2023, so this marks the first college coaching position of his illustrious career.

Also Read: PHOTOS: Bill Belichick’s GF Jordon Hudson Reveals Her Real Age For The First Time With Custom Bday Gift, And She’s Even Younger Than We Thought