Tom Brady breaks out in laughter after question about Bill Belichick’s girlfriend Jordon Hudson

Tom Brady breaks out in laughter after question about Bill Belichick’s girlfriend Jordon Hudson

Tom Brady couldn’t help but crack a smile when he was faced with a pair of questions about Bill Belichick’s relationship with 24-year-old Jordon Hudson. 

The questions were a part of Brady’s sit-down on “Sundae Conversations with Caleb Pressley,” a satirical interview series hosted by Pressley, the former Barstool Sports personality, that also features another ex-Barstooler Glen “Glenny Balls” Medoro. 

The pair of questions that really seemed to break Brady came at the very end of the video that was released Sunday. 

Pressley asked the seven-time Super Bowl champion and future Hall of Famer if Belichick, 72, had followed his TB12 Method, to which Brady responded, “Nah, he’s a big carb guy.” 

The host then pivoted to poking fun at Hudson and Belichick’s relationship. 

Tom Brady chuckled during the interview. Sundae Conversation/YouTube
It’s not the first tome Caleb Pressley has gotten a guest to laugh. Sundae Conversation/YouTube

“What about his girlfriend? She looks as young and healthy as ever?” Pressley asked.

“Yeah, sounds like it,” Brady replied before briefly pausing as the two stared at one another. 

“I don’t know, I don’t follow it too much,” Brady finally added. 

That’s when Pressley followed up with a question that left Brady trying to regain his composure after laughing so much. 

Bill Belichick and Jordon Hudson attend the 14th Annual NFL Honors at Saenger Theatre on February 06, 2025 in New Orleans, Louisiana. Getty Images

Pressley joked that Hudson is under 25 — the legal age to rent a car — and asked if Brady would be willing to rent a car on her behalf.

“I don’t want any liability,” Brady finally said after he stopped laughing. 

Hudson and Belichick’s relationship went public last summer. 

Since then, the two have been open about it and have been spotted out in public and attending events together. 

Hudson was in New Orleans last week for the Super Bowl with Belichick, appearing with him at NFL Honors on Thursday.

She was even spotted hanging out with comedian Nikki Glaser at the Super Bowl.

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