On a recent episode of the “BFFs” podcast, Barstool Sports founder Dave Portnoy delved into the topic of Bill Belichick’s relationship with Jordon Hudson, reacting initially with a mix of surprise and disapproval. “Yikes. Ew. Wow,” he exclaimed upon discussing the couple’s significant age difference.
Belichick, the former NFL coach, is 72 years old, while Hudson, a former cheerleader, is 24.
Despite his initial reaction, Portnoy quickly shifted the conversation to challenge the societal judgment surrounding age-gap relationships.
Co-host Brianna Chickenfry highlighted the vast age disparity, but Portnoy dismissed concerns, emphasizing that he does not personally judge such situations.
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He defended the couple’s relationship by recounting how they met: “It’s a big gap. You guys have problems with age gaps,” he noted. “That’s fine. I don’t judge. They met naturally over her homework on a plane. … They’re in love.”
Adding a personal touch to the discussion, Portnoy mentioned that he might encounter the couple during his visits to Nantucket, where Hudson reportedly owns a property.
This led to playful banter with Chickenfry, who made a quip about Portnoy’s own history of dating younger women, comparing him to Belichick with a joke that the coach “gotta be 47.”
Portnoy himself has been in the public eye for his relationships, notably being seen with 25-year-old Camryn D’Aloia at a Boston Celtics game, and later bringing her to a recording of Alex Cooper’s “Call Her Daddy” podcast.
He expressed frustration with Cooper for hinting at D’Aloia being his new girlfriend, which he denied. Before D’Aloia, Portnoy had a more than two-year relationship with 29-year-old model Silvana Mojica, which ended in 2023.
As for Belichick, he had a 16-year relationship with Linda Holliday before starting his relationship with Hudson.
The couple’s relationship came to light under rather sensational circumstances, with Belichick being caught on a Ring camera shirtless, sneaking out of Hudson’s Massachusetts home.
Despite efforts to keep their relationship private, they were spotted together on Belichick’s boat in Nantucket shortly before the podcast aired.
Portnoy’s discussion on his podcast reflects the complexities and varying opinions that often accompany public figures’ personal lives, especially when it involves significant age differences. The conversation navigates the boundaries between personal judgment and public interest, highlighting how these relationships are scrutinized in the media and popular culture.
