Tom Brady breaks down laughing after brutal joke about Bill Belichick and his 24-year-old girlfriend

Tom Brady struggled to contain his laughter as interviewer Caleb Pressley took a brutal shot at Bill Belichick during an episode of Sundae Conversation.

The NFL legend sat down for the chat ahead of Super Bowl LIX, and held his own as he faced questions about his past quarterback mistakes, his minority ownership of the Las Vegas Raiders, and whether he still believes in Bitcoin.

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However, he finally cracked when Pressley brought up Belichick’s 24-year-old girlfriend, Jordon Hudson.

The couple’s 48-year age gap has been subject to plenty of barbs from the NFL community since they went public with their romance last summer.

And Pressley, who left Barstool Sports last month, couldn’t resist the opportunity to press Brady on the relationship.

He started by asking the retired quarterback about TB12 – the diet and workout regime he uses to stay in incredible shape – questioning if Belichick also uses it.

“Nah, he’s a big carb guy,” Brady responded, speaking of the coach he won six Super Bowls with.

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

The suggestion drew a smile from Brady, who admitted he doesn’t follow Belichick and Hudson’s relationship closely.

“If Bill Belichick’s girlfriend needed it, would you rent a car for her?” the interviewer then asked, referencing the fact that Hudson can’t do that without paying a ‘young renters fee’ under the age of 25.

At that moment, Brady lost control and broke down laughing.

He turned red as he tried to keep his laughter in for a few seconds, before cracking up into giggles.

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Pressley, of course, is not the only person to poke fun at Belichick and Hudson’s relationship in recent weeks.

The couple attended last week’s NFL Honors ceremony, and became the punchline of Snoop Dogg’s opening monologue after walking the red carpet.

“I’ve been a football fan for a long, long time,” the rapper said.

“I remember back when the Cowboys was good, I remember back when the Chiefs was bad, and I remember (when) Bill Belichick’s girlfriend wasn’t even born yet.”

Cameras then cut to the couple, with the former NFL coach appearing amused, while Hudson was left shocked.

Despite facing plenty of public scrutiny, the pair are still going strong and this week celebrated their ‘Meetiversary’ – having first crossed paths four years ago.

To mark the milestone, Hudson shared a post on her Instagram account.

“February 11th, 2025 – February 11th, 2021. Happy Meetiversary Bill Belichick,” she wrote.

“Cheers to the fact that you still let me give you lengthy philosophical lectures four years later.”

Hudson’s caption was a reference to the second slide of her post, which featured a video of her opening up the book that she had Belichick sign when they first met in 2021.

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The message included the date and read, ‘Jordon, Thanks for giving me a course on logic! Safe travels!’

Belichick signed the book with his name, and all the Super Bowls he had won.

Hudson also appeared to fire back at trolls who claimed she was wearing one of Belichick’s Super Bowl rings at the NFL Awards.

“P.S. that Championship Ring is mine,” she wrote, confirming the one she wore was from when she won the national championships in cheerleading with Bridgewater State University.