Bill Belichick takes relaxing ride with 23-year-old girlfriend as NFL training camps kick off

Article content

This is a new one for Bill Belichick: For the first time in decades, he’s not at training camp to prepare for the coming NFL season. 

How long has it been since the NFL legend didn’t have to worry about head-coaching duties at this time of the year? The year 1999, when he was still assistant head coach and defensive coordinator for the New York Jets. 

That also happens to be two years before his current girlfriend, Jordon Hudson, was born. 

But it appears that the happy couple are enjoying the summer weather in Nantucket, seemingly without a care in the world. The pair were spotted riding bikes together on Tuesday in the Nantucket beach town where Belichick built a compound.

Hudson showed off a pink sports bra and black leggings while the former coach wore a short-sleeved blue windbreaker and shorts for the ride.

Hudson was spotted last week at the Best of Boston 2024 Soirée solo at Roadrunner in Brighton with another former cheerleader.

According to a report by TMZ last month, Hudson moved into the coach’s home in Hingham, Mass., at the beginning of the year.

The outlet also reported that since then, the duo have been inseparable while still managing to keep out of the public eye until recently.

Last month, Belichick was seen taking Hudson out for a morning cruise on his boat named VIII Rings — a not-so-subtle nod to the number of Super Bowl championships he has won as a coach and coordinator during his illustrious NFL career.

According to Britain’s Daily Mail, the duo had been holidaying in one of the future football hall of famer’s seven properties on Nantucket, six of which make up a “compound” worth an estimated US$15.7 million.

The news outlet also reported that Belichick’s family has been vacationing on his properties while the couple has been there.

Hudson had previously posted snaps on social media from the exclusive island, though none featured Belichick.

The couple attended Tom Brady’s Patriots Hall of Fame ceremony earlier this month and were seen together in a video posted on social media. In the clip, Belichick is greets several former Patriots players with Hudson in tow. Belichick’s daughter Amanda, 40, also appears in the video.

Fans have been going wild over the couple’s recently revealed relationship, which initially came to light after a report by TMZ in June.

Belichick and Hudson, whose age gap is nearly a half century, reportedly have been dating since 2022.

The pair met on a flight from Boston to Florida and hit it off immediately, according to reports.

The two were said to have bonded on the flight over Hudson’s project on philosophy and the seven-time Super Bowl-winning coach went as far as to sign a copy of her textbook, Deductive Logic.

The duo exchanged contact information during the flight and maintained a friendly relationship as Belichick was still in a relationship with longtime girlfriend Linda Holliday.

However, the New York Post‘s Page Six reported in September 2023 that Belichick and Holliday had “been involved in a drawn-out, back-and-forth breakup for nearly a year.”

It was during this time that things between the couple reportedly became romantic.

In fact, it was reported by the Daily Mail that the viral footage of a man appearing to be a shirtless Belichick leaving a house early one November morning last year was in fact the coach.

Furthermore, the outlet confirmed that he was exiting the Massachusetts residence of Hudson.