Bill Belichick and girlfriend, 24, lock arms during Nantucket date

By Emma James In Nantucket, Massachusetts, For Dailymail.Com

21:00 20 Jun 2024, updated 21:03 20 Jun 2024

Former Patriots coach Bill Belichick and 24-year-old girlfriend Jordon Hudson brushed off media attention and doubled down on their May-December romance during a swanky dinner date in Nantucket. 

The 72-year-old NFL legend and the former cheerleader enjoyed a double date with two friends at secret private members club, The Boarding House, on the New England island Wednesday night, DailyMail.com can reveal.

The unlikely couple were spotted on the Massachusetts summer destination earlier that day, for the first time since their relationship came to light last week. 

Belichick has reportedly been dating Hudson since at least 2022, after his 16-year relationship with Linda Holliday, 62, broke down.

And now, exclusive DailyMail.com photos show the former collegiate cheerleader and pageant queen wasn’t too shy about showing some PDA with her older beau, with Hudson keeping a tight grip on his arm as they left the restaurant Wednesday night. 

Hudson showed off her youthful, playful style, donning a white tank top paired with pink floral pants, and wedge sandals. 

She cozied up to her much older beau, who was dressed down in a blue linen shirt, blue jeans, and brown loafers. 

The couple, who have a 48-year age gap, had been keeping a low profile since reports of their relationship made headlines.

But the two appeared unfazed by the media attention on Wednesday, laughing and clutching at each other during and after their two-hour dinner. 

Belichick even showed his new lady friend that chivalry is not dead by dropping  her and two friends off at the restaurant first, before parking nearby.

They enjoyed their meal before walking to a nearby ice cream store for dessert, with Belichick remaining in the car to whisk Hudson away as soon as she was done.

He even opened the door for her to get into the car and seemed to be trying to avoid prying eyes of fans – driving away after a group of young boys spotted the NFL legend.

Hudson slipped her arm in Belichick’s as they left the exclusive restaurant, smiling up at him and laughing as they strolled down the cobbled street.

The existence of the club, which Hudson follows on social media, has been kept so quiet that it is only accessible to certain members of staff at the restaurant.

With a velvet blue interior and custom-made artwork, the basement establishment is part of the swanky Boarding House and Pearl restaurant group in central Nantucket.

Only those who are investors or members can access the secret underground speakeasy, which is protected from prying eyes by a code activated door.

The property reopened last spring after undergoing a refurbishment and had always denied claims that it would be a private members club.

Representatives for Blue Flag Partners insisted that the restaurants would be ‘open to the public’, but also open for ‘private group bookings.’

Despite their assurances, the speakeasy was still opened in the basement, for a limited number of patrons who could tuck into $28 oysters, spicy tuna crispy rice with caviar for $36 and $38 specialty cocktails.

Hudson was spotted again on Thursday morning this time without her much older beau. 

She was seen taking a stroll in athletic wear to a Belichick’s favorite nearby market alone to purchase an iced coffee, smiling at her phone as she walked back to the property.

Neither seem to have a care in the world and are openly flaunting their relationship on the exclusive isle.

It comes after DailyMail.com revealed the first photos of the couple together, sunning themselves on Belichicks $225,000 powerboat, named VIII Rings for his eight Super Bowl titles (six as head coach in New England and the two he previously won as the New York Giants’ defensive coordinator).

The pair have been hunkering down in one of the legendary NFL coaches lavish properties in his ‘compound’ on Nantucket.

Belichick and Hudson have been staying in one of his seven lavish properties on that he owns on the exclusive island, with an estimated value of $3million. 

He currently owns at least seven properties on the island, with six of them close to each other making up a complex in Siasconet, worth in total $15.7million.

Belichick and Hudson have been enjoying the sunny weather at the three bedroom and three-bathroom property, which offers privacy from every angle.

It isn’t the first time that Hudson has visited the island, posting on social media from the exclusive enclave in May.

The couple are currently holidaying with Belichick’s son Brian, his wife Callie, and their young child.

His daughter-in-law Jennifer Schmitt is also staying at the complex with her young children, though it is unclear if her husband Steve has joined the family.

Both Brian and Steve married their spouses on the island, with Callie posing for pictures in front of one of the properties.

Belichick originally bought a home on the island in 1979 and has spoken of his love for the island.

Speaking to N Magazine in 2017 he said: ‘The island is spectacular. The people are great, fishing, bike paths, the lighthouses, the beach, the history — I mean it’s got it all.

‘The baked goods there are pretty hard to resist, especially their muffins or cookies.’

It comes after DailyMail.com revealed footage of Belichick sneaking out of his girlfriend’s home in 2023 – months before their relationship was revealed.

Legendary quarterback Tom Brady mocked Ring footage of the football coach doing a bare-chested walk of shame at his roast in April.

Brady, who joked about his beloved coach doing the walk of shame on his Netflix roast, seemingly had no clue the home belonged to Belichick’s new girlfriend.

Seemingly unbeknownst to Tom – and his Netflix audience of millions – Belichick, 72, has been dating Hudson since 2022 after the pair met on a flight from Boston to Florida in 2021, as reported by TMZ.

The pair are said to have bonded over a philosophy project that Hudson – a student-athlete as well as an entrepreneur – had been working on at the time.

On Tuesday, the May-December couple were pictured in an unearthed selfie taken during their first encounter in February 2021, TMZ reported.

The two posed for a photo during their reported first meeting aboard a 2021 flight from Boston to Florida where Belichick reportedly struck up a conversation about the book she was reading.

It was on that flight that Belichick also purportedly autographed a ‘Deductive Logic’ textbook that Hudson, then a 21-year-old student at Bridgewater State University, was studying.

Both had been keeping their relationship under wraps after his long-drawn-out break up with his ex-girlfriend Lisa Holliday.

The Ring footage, believed to be from November last year shows the New Haven legend shirtless, opening the front door of Hudson’s $800,000 Massachusetts property in the early hours of the morning.

Belichick, who has won a total of eight Super Bowls, grimaced at his former star player and looked uncomfortable during the show.

He spent 23 seasons as head coach of the New England Patriots, taking charge of the team in the same year his current girlfriend was born.

Neither Belichick nor Hudson have commented on their relationship, though she attended Brady’s Patriots Hall of Fame induction ceremony this week.

Belichick was spotted rooting her on at a cheerleading competition in March, and posed for a picture with her during a work trip to Croatia on a boat.

The couple kept in touch after their airline meet cute, discussing the former Bridgewater State University student’s schoolwork and cheerleading routines.

They initially kept things lowkey and were only briefly spotted on rare occasions, but TMZ claims Hudson secretly visited Gillette Stadium to support her man during the 2022 and 2023 seasons with the Patriots.

Hudson is even understood to have been helping Belichick with his business endeavors of late.

Page Six broke the news that the all-time great NFL coach – who called time on his legendary Patriots tenure earlier this year – had broken up with Holliday last September after a drawn-out, back-and-forth breakup for nearly a year.’

After bidding an emotional goodbye to the Patriots, Belichick failed to land another NFL job ahead of the 2024-25 season.

He is instead set to become a regular fixture on ESPN’s Monday Night Football with Peyton and Eli Manning, before potentially returning to coaching when a vacancy opens up.