Tom Brady was put on the spot during an interview and was forced to react to Bill Belichick’s romance with Jordon Hudson, who is 48 years younger than the famed coach. The awkward moment came when Brady appeared on the “Sundae Conversation.” Near the tail-end of the interview, he was asked if anyone he knew used his TB12 workout program. “What about [Belichick’s] girlfriend, she looks as young and healthy as ever?” host Caleb Pressley asked. Brady did his best to sidestep the topic of his former coach’s young squeeze. “Sounds like it … I don’t know, I don’t follow it, you know, too much,” the “NFL on Fox” analyst responded. That’s when the convo became very uncomfortable for Brady. “If Bill Bellichick’s girlfriend needed it, would you rent a car for her?” Pressley asked, referring to Hudson only being 24 years old. After a long pause, Brady couldn’t hold back the laughter. “I don’t want any liability,” he replied through laughs.

That wasn’t the first time the former NFL quarterback had some laughs at Belichick’s expense. A few months earlier, Brady joked about his fallout with Belichick by posting a clip of his “NFL on Fox” colleague Jay Glazer playfully kicking him off the set. “Jay doing his best ‘Bill Belichick after the 2019 season’ impression,” Brady tweeted in December 2024 alongside the clip.

Just a few days before that tweet, info about Belichick and Hudson’s relationship was published. According to someone in-the-know, the pair were unbothered by those critical of their age difference. “Jordon is an old soul so she and Bill connect on a deep level,” the insider told Page Six at the time. “Age is just a number to them,” the source added. Around that time, the pair appeared on the red carpet together.

Bill Belichick made his public debut with his much younger girlfriend, Jordon Hudson, at the American Museum of Natural History Gala in December 2024. It was their first time walking the red carpet as a couple, but the University of North Carolina coach and the former cheerleader made their romance Instagram official a few months earlier. In September 2024, Hudson uploaded a photo of her and Belichick rubbing horned goats. “This is my formal petition for @BillBelichick to change his handle to @ BillyGoat !! … Welcome to the ‘Gram, Billy!!!!” she wrote in the caption.

That was Hudson’s first time posting the NFL coaching legend to her page, but as time went on, he became a fixture in her uploads. On February 7, Hudson shared a snap of the couple rocking formal wear at the NFL Honors. She wore a revealing glitzy gown with a cut-out midsection, while Belichick sported a blazer. He accessorized his outfit by adorning his fingers with his Super Bowl rings. A few days later, Hudson paid homage to her beau when she attended the 2025 Super Bowl in a customized leather jacket. “And yes, that is an up-cycled leather jacket with time-contextual, historically accurate patches corresponding to BB’s lifelong football career,” she wrote in the lengthy Instagram caption showing off the jacket. “And yes, I designed and created this piece with my own bare hands,” Hudson added.

Days later, Hudson celebrated the couple’s four-year “Meetiversary” in another post. She uploaded a photo of their hands folded over each other while wearing Belichick’s Super Bowl rings. “Happy Meetiversary @billbelichick — Cheers [cheer emoji] to the fact that you still let me give you lengthy philosophical lectures four years later,” Hudson penned in the caption.