‘Well Played, Sir’: Tom Brady Can’t Hide His True Feelings When Asked About 72-Year-Old Bill Belichick and His 24-Year-Old Girlfriend
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Football legend and Raiders minority owner Tom Brady couldn’t contain his laughter when the topic of his former coach Bill Belichick’s relationship with 24-year-old Jordon Hudson came up during a recent interview.
The seven-time Super Bowl champion, who just wrapped up his widely praised hosting duties at Super Bowl LIX, where the Philadelphia Eagles destroyed the Kansas City Chiefs, turned bright red while fielding questions on the Feb. 9 episode of comedian Caleb Pressley’s “Sundae Conversation” YouTube series.
Brady, widely regarded as the greatest quarterback of all time with his record-breaking 23-season NFL career and unprecedented championship success, was visibly flustered after Pressley seemingly tricked him into admitting his Hail Mary pass on the final play of the New England Patriots’ 41-33 Super Bowl 52 loss to the Eagles in in 2018 was a mistake.
It only got worse (or funnier) when he started probing about the 72-year-old coach’s relationship with Hudson, who is nearly five decades his junior.
The hilarity ensued when discussing Brady’s famous TB12 Method, the holistic health and fitness approach he credits for his longevity in the sport.
When asked if his former Patriots teammates Julian Edelman, Wes Welker, and Randy Moss had tried the program, Brady was comfortable and engaged. But when Pressley pivoted to ask, “Did Bill Belichick follow TB12?” Brady’s composure began to crack.
“Nah, now he’s a big like carb guy,” Brady replied, still maintaining his cool.
Then came the knockout punch when Pressley followed up with: “What about his girlfriend? She looks as young and healthy as ever.”
Trying desperately to keep it together, the NFL icon responded with an unsettling giggle, “Sounds like it. … I don’t know. I don’t follow too much.”
But the comedian wasn’t finished. In what became the interview’s most memorable moment, Pressley asked, “If Bill Belichick’s girlfriend needed it, would you rent a car for her?”
That’s when Brady completely lost it. Turning a deep shade of red, the quarterback laughed, “I don’t want any … liability.”
Viewers on YouTube were thoroughly entertained by Brady’s reaction.
“The bellicheck gf car rental joke was insane,” one commenter wrote.
Another added, “‘I don’t want any liability.’ Well played sir, well played.”
“That rental car line is legendary,” one person said, as another added in the reply, “That’s how I choose my girlfriends from. Now on, if they can’t rent a car or not.”
When someone asked for an explanation of the joke, a fan attempted to clarify: “Bill bellichicks GF isnt old enough to rent a car, Tom Brady is the spokesperson for Hertz rental cars.” Actually, Hudson at 24 is old enough to rent a car, but companies like Hertz will charge higher rates for drivers under 25.
“I gotta admit the host is very good at breaking stones. It’s impressive doing that with Tom Brady,” one commenter noted.
Page Six also posted the clip on X, where one person admitted, “Took me a minute to think about the rental car age requirement.”
took me a minute to think about the rental car age requirement
— Aconn113 (@AaronCo50952820) February 11, 2025
On the website, readers chimed in with their own takes.
“Tom is not speechless. He is a good actor. He simply chose to laugh and to brush off the question,” one person wrote, adding, “Brady, like all of us, feel that Bill Belichick is being used. But Tom would never say this… The rest of us would and do!!”
Another reader commented: “If Belichick were an unknown 72 year old hanging with a girl who’s ’23 one day, 24 the next, then 23 again two months later’ the cops would be all over him for probable human trafficking.”
Belichick and Hudson reportedly met in February 2021 when she was just 20 years old, crossing paths on a flight where the coach signed her “Deductive Logic” textbook.
Their relationship has drawn significant attention due to the 48-year age gap, with even Snoop Dogg joining those roasting the couple.
According to sources, Hudson insists their connection isn’t about money or status but rather a shared passion for “strategic thinking” and historical war strategies — an interest that aligns with Belichick’s meticulous approach to football. They also allegedly share a love for nature and seagulls.
Meanwhile, Brady continues to expand his impressive post-NFL portfolio, which includes his $375 million broadcasting deal with Fox Sports, a part ownership of the Las Vegas Raiders, his TB12 wellness empire, and numerous successful business ventures – proving he’s still winning off the field, even if he occasionally gets caught off guard by questions about his former coach’s love life.
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