Bill Belichick’s romance with Miss USA contender shocks the pageant world

NFL legend’s relationship with 24-year-old beauty queen

Speculation over Jordon Hudson’s relationship with Bill BelichickInstagram @jordon_isabella

NFL legend Bill Belichick, 72, is reportedly dating 24-year-old beauty queen Jordon Hudson. Hudson, a standout in the Miss USA pageant circuit, has been a contender since 2019, but her romantic involvement with Belichick, whom she met on a flight in 2021, has now taken center stage.

Hudson’s pageant peers were taken aback by the news. “I didn’t even know she had a boyfriend,” said one former competitor from Miss Massachusetts Teen USA 2020. “He’s old enough to be her grandfather! I didn’t realize she’d go as far as to date someone in his 70s for fame.” Hudson, first runner-up for Miss Maine 2024 and third runner-up in Miss Massachusetts Teen 2020, has always been seen as unconventional among her peers.

The relationship’s origins are as surprising as the pairing itself. Belichick, known more for his stoic presence on the sidelines than for commercial flights, reportedly met Hudson on a flight from Boston to Florida. A photo obtained by TMZ shows the two during their initial encounter, with Belichick signing her “Deductive Logic” textbook. This chance meeting sparked a romance that saw Hudson receiving lavish gifts, such as a white Porsche, and making grand entrances at high-profile events like Tom Brady’s Hall of Fame induction.

Jordon Hudson: Beauty queen & entrepreneur

Hudson’s background is equally intriguing. A former student-athlete and philosophy major at Bridgewater State College, she made the Dean’s List in Spring 2021 and holds a cosmetology license. Despite her academic achievements, she has yet to graduate officially. Professionally, she is the CEO of Trouble Cub Enterprises, though the nature of the business remains unclear. Hudson also has a keen interest in property, owning two homes in the Boston area, which she does not currently inhabit.

Friends and fellow contestants describe Hudson as outgoing and ambitious, often willing to take bold steps for attention. Her relationship with Belichick, marked by a significant age gap, has certainly made waves. “She’s not afraid to go up to a guy at a bar and say hey,” a source noted. The couple’s public outings, including a recent boat trip around Nantucket, have only fueled the fascination and speculation surrounding their relationship.

Despite the public interest, Hudson has remained silent, not responding to requests for comment. Her involvement with Belichick, however, continues to captivate the public and her peers, highlighting an unexpected chapter in the life of one of the NFL’s most prominent figures and a rising star in the beauty pageant world.