Life has suddenly become more complicated for football legend Bill Belichick on his island retreat off the coast of Massachusetts.
After his young lover Jordon Hudson slammed his old squeeze Linda Holliday, all three have found themselves on the 45 square miles that make up Nantucket.
Perhaps that is why Belichick, 73, decided to whisk Hudson, 24, back to the mainland on Wednesday, jetting off in style to tony Saratoga Springs, New York, for a ‘Grand Reopening’ of a hotel after a $90 million refit.
The University of North Carolina head coach showed Hudson the meaning of his millions by splurging $5,000 for a private jet to the event at the 148-year-old Adelphi Hotel.
And noted horse race fan Belichick made sure they were in Saratoga just in time for Thursday’s first day of racing at the July 4th Festival.
The couple, who have a 49-year age gap, had been hunkering down at the six-time Super Bowl winner’s luxury compound on Nantucket since returning to the exclusive enclave off the Massachusetts coast.
Bill Belichick, 73, and his much younger lover Jordon Hudson, 24, jetted off to Saratoga Springs for the weekend from his luxury compound in Nantucket
The couple were all smiles for the cabin crew as they arrived at the private terminal at Nantucket Airport in preparation of jetting off to upstate New York
DailyMail.com photos showed the couple disembarking off a Cessna Citation Latitude jet owned by NetJets on Wednesday afternoon
The May-December couple showed they have very different ideas of how to dress for a private flight. Jordon, 24, was glammed up in a floral tea dress, clutching a white boater with a light blue bow, while the 73-year-old North Carolina football coach schlumped around in a university sweat shirt, jeans, untied sneakers and a baseball cap
They boarded a NetJets-owned Cessna Citation Latitude jet at Nantucket airport on Wednesday afternoon. They landed in Saratoga 45 minutes later.
The duo were all smiles as they headed off with Hudson smiling demurely at their pilot greeting them.
Brunette beauty Hudson donned a vintage tea dress adorned with roses and paired it with a green bag with gold detailing and kitten heels.
She drove the former New England Patriots coach to the island’s airport, smiling sweetly and pushing her sunglasses atop her head as her beau shook hands with airport staff.
Belichick pulled a small suitcase with his college team’s logo emblazoned on the front to the private terminal, along with a large tote bag covered in lobsters.
After unloading their vehicle to board the jet, Belichick lugged a bag with his UNC emblem and a tote bag with red lobsters on it. Hudson used a garment bag as a makeshift umbrella
Hudson and Belichick arriving in Saratoga Springs right in time for the holiday weekend horse races
Belichick and Hudson arrived at the 148-year-old Adelphi Hotel in Saratoga Springs on Wednesday
Hudson used his Saks Fifth Avenue suit bag as an umbrella from the intermittent rain, clutching a straw hat adorned with the UNC cornflower blue ribbon.
The couple have been doing their best to cut a low profile after returning to Belichick’s compound in Siasconset on the east coast of Nantucket –rarely venturing into the island’s commercial area where his ex love Holliday lives.
When they did go into town, they were seen in a terse exchange, looking stressed before stonily going their separate ways.
Hudson cut a lonely figure as she indulged in some solo retail therapy on the cobbled streets of the island.
Brunette beauty Hudson donned a vintage tea dress adorned with roses and paired it with a green bag with gold detailing and kitten heels while Belichick opted for a casual look consisting of jeans, a long sleeve gray top and a pair of Nike sneakers
She went into several high-end stores, wearing $300 Gucci sunglasses, paired with $1,000 Jimmy Choo slip-on sneakers and a $3,5000 Bvlgari snake tote bag.
She also wore a small gold snake ring and added a matching bracelet to her outfit while heading to Saratoga.
Hudson has been keen to keep their loved-up image going strong, posting a photo of her older lover holding her hand on her Instagram story.
It is unclear if the recent criticism of their relationship in the public eye is finally taking its toll, or if the couple has been finding their return to the island uncomfortable following Hudson’s public digs at Holliday.
Hudson clutching an elegant white wide-brimmed hat – a popular choice for many horse racing fans
Belichick walked up to the hotel maintaining his casual air with his hand in his pocket as he handed luggage to the hotel staff
The Daily Mail can reveal that they have been hunkering down in his compound, relaxing with popcorn and cooking for each other after ruffling feathers by showing up together at the Nantucket Film Festival over the weekend.
Belichick and Hudson went to Saratoga for the ‘Grand Reopening’ of the Adelphi Hotel after a $90million refit
As we revealed, Hudson called Holliday ‘pathetic’ and ‘delusional’ after discovering a personal email she sent to Belichick during their 16-year relationship.
Belichick and Holliday, 62, broke up in September 2023 after 16 years together. He met Hudson on a flight from Boston to Florida in 2021.
There has been speculation over the timeline of Belichick and Hudson’s relationship but a new report in People has claimed his relationship with Holliday had long been over when he started dating the former cheerleader.
‘Many assumed that Bill had cheated on Linda through 2022 and 2023, but they were broken up by September 2022,’ a source said.
‘Linda was still pretending they were together after the breakup, and Bill played along so she could transition with the least amount of public humiliation and avoid abrupt displacement.
‘Bill moved into a hotel nearby Gillette Stadium in September and allowed Linda to continue to stay in his homes.’
Belichick and former flame Linda Holliday broke up a year before their separation had been officially revealed – contradicting the long-standing rumor that he had cheated on her, People magazine reported
Hudson branded a personal letter alleged penned by Holliday to Belichick in 2015 as ‘pathetic’ and ’embarrassing’
Belichick and Hudson made the trip to Saratoga just in time for Thursday’s first day of racing of the four-day July the 4th Festival
Another source added that they had ‘been pretty separate for a while’ and they were dealing with problems that were ‘not new’ when they finally went their separate ways.
Tensions between Hudson and Holliday have been high for months. The two are said to have had a feisty exchange at a Christmas event in Nantucket towards the end of last year.
It ramped up last week though when Hudson engaged in the testy Instagram exchange after being called a ‘gold digger’ by a user she believed was Holliday’s close friend.
Hudson claimed that she ‘found’ the letter at Belichick’s home near Boston, and sent a picture of it to her supposed friend, insisting that Holliday should ‘burn it.’
Holliday declined to comment when contacted by Daily Mail. Hudson did not respond.
