In a recent turn of events, Barstool Sports founder Dave Portnoy has entered the fray regarding the ongoing saga surrounding Bill Belichick.
The 73-year-old coaching titan, celebrated for his unparalleled record of Super Bowl victories, has grabbed headlines not just for his strategic prowess on the football field, but for his romantic entanglement with 24-year-old Jordan Hudson.
The controversy ignited following Belichick’s appearance on a CBS Sunday Morning interview with host Tony Dokoupil, where the discussion was ostensibly meant to center around Belichick’s new book, “The Art of Winning.”
However, the interview took a bizarre turn as Hudson seemingly took the reins, reacting defensively when Dokoupil inquired about the origins of their relationship.
According to Hudson, the couple’s fateful meeting occurred on a plane bound for Palm Beach, Florida, back in 2021.
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Yikes: This has to be the most awkward Bill Belichick interview he’s ever done…
Something strange is going on with Jordon Hudson.
(via @CBSSunday) pic.twitter.com/jtWbF45z9N
— Dov Kleiman (@NFL_DovKleiman) April 27, 2025
Following the awkward CBS segment, Belichick issued a rare statement criticizing the network for straying from the agreed-upon topic.
“Unfortunately, that expectation was not honored during the interview. I was surprised when unrelated topics were introduced, and I repeatedly expressed to the reporter, Tony Dokoupil, and the producers that I preferred to keep the conversation centered on the book,” Belichick’s statement read. “After this occurred several times, Jordon, with whom I share both a personal and professional relationship, stepped in to reiterate that point to help refocus the discussion.”
The CBS network countered Belichick’s claims, stating, “When we agreed to speak with Mr. Belichick, it was for a wide-ranging interview. There were no preconditions or limitations to this conversation. This was confirmed repeatedly with his publisher before the interview took place and after it was completed.”
Many observers, including Portnoy, have cast doubt on the authenticity of Belichick’s statement, suggesting it may have been penned by Hudson herself.
Further complicating matters, TMZ reported that CBS had to trim 30 minutes from the interview, revealing that Hudson reportedly exited mid-conversation, expecting Belichick to follow suit.
SHOCKER: TMZ Is Reporting That Bill Belichick’s Disastrous CBS Interview Was Even Worse Than What Aired. They Had To Cut 30 Minutes From It, and “Jordan Hudson Stormed Out In The Middle Of It And Expected Bill To Follow Her” pic.twitter.com/c8ZnaPJWr7
— Barstool Sports (@barstoolsports) April 29, 2025
Concerns are mounting regarding the nature of Belichick’s relationship with Hudson, especially after the New York Post reported that Hudson has remarkably built an $8 million real estate portfolio since their relationship began.
“Hudson, 24, acquired three multi-family homes in the Boston area in December 2023 for approximately $7.5 million—signing substantial mortgage agreements in mere days, according to documents reviewed by Realtor.com,” reported the New York Post.
“Merely two months prior, Hudson purchased a cottage in the picturesque Cape Cod town of Harwich for $610,000, which she listed as her home address on the mortgage documents,” the report continued.
Megyn Kelly has gone so far as to suggest the situation resembles elder abuse.
Portnoy, meanwhile, has shared additional insights into the peculiar dynamics of Belichick’s relationship with Hudson.
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