EXCLUSIVE Revealed: How Bill Belichick wooed his ex - and then dropped her like a hot potato when cheerleader Jordon came along

Daily Mail​

11 hours ago

For a man renowned for meticulous planning, it was a classic move.
Bowled over by the woman he'd met at a nightclub in ritzy Palm Beach the night before, NFL legend Bill Belichick sent her a gorgeous bouquet of flowers.
His message to the object of his desires, Linda Holliday, said simply: 'Thanks for a wonderful evening.'
It worked its magic.
Holliday, who'd been on a girls night out in the Florida beach town, reportedly dumped her then boyfriend for divorced Belichick.
The couple were to spend the next 16 years together – before Belichick, now 73, controversially moved on to glamorous ultra-age-gap girlfriend Jordon Hudson, 24.
That Florida night in 2007 was the start of a relationship that saw Belichick and Holliday, 62, become a celebrated power couple in Boston where he led the New England Patriots to six Super Bowl victories.
Yet for her, the apparent gloss of switching from selling X-Ray medical equipment for a living to presenting a fashion segment called Style Boston on local TV wasn't always a bed of roses.
How do we know? Enter Hudson, once more, into the equation.
She passed on an impassioned letter between the former couple to a woman she believed was a close friend of Holliday and who'd branded her a 'gold digger' during a spat on Instagram.
As DailyMail.com exclusively revealed, Hudson told the woman she'd 'found' the printed out email penned by Holliday in an old invoice file at her lover's $2.2million home at Hingham, 15 miles south of Boston.
Written in 2015, the missive is a toe-curling insight into a relationship and ends with the hand written plea from Belichick's ex: 'In the end, all I really want is for you to… hug me.'
The printout – also finished with a hand drawn heart – reveals Holliday was apparently feeling the shadow of something not unfamiliar to women living with a hugely successful divorced man… the former wife.
Large parts focus on Belichick's ex Debby, the mother of his three children, who is mentioned in less than flattering terms for her continued center place in the life of a legend now coaching the University of North Carolina.
On the surface, the couple's existence together appeared ideal as Holliday staunchly supported Belichick at Patriots games and he devoted time to her extensive breast cancer research charity work.
In 2019, she gushed to CBS Boston in a TV interview at the team's Gillette Stadium about her life with the coach and manager, whose foundation she co-founded in 2013.
Holliday – a former beauty pageant contestant like Belichick's new amore Hudson – discussed his 'softer side'.
Bill Belichick's much younger girlfriend, Jordon Hudson, delivered a scathing message to his ex-girlfriend after finding a private email between the exes
Beaming, she said: 'It doesn't take much to make him smile actually.
'In 12 years together, Bill has been so dynamic supporting the causes that are close to me and actually supporting me. And I value and love that about him.'
In a suite overlooking the field, she said in awe: 'It's breathtaking, isn't it. From where I sit I have a direct view of Bill and the team. It is a second home.'
Of the Bill Belichick Foundation and the Breast Cancer Research Foundation, she continued: 'Those are near and dear to my heart. Beside the Patriots those are my two other teams.'
Passing a large framed photo of Belichick waving, Holliday recounted excitedly: 'That's the wave.
'He'll turn around on his way to shake the opposing team coach's hand and he gives myself a wave and he gives his daughter who's in another suite a wave.'
And of her support, she told the interviewer: 'It's kind of within the family that it makes you feel good that you're supporting him, and you saw the happiness from this win and the love that he has for this game and for the fans.'
The exact reality of the couple's relationship at that time is not known. However, four years earlier when mom-of-two Holliday wrote her desperate note she was clearly not feeling the warm glow of his support as much as she would like.
Holliday, who obtained a radiography degree from Vanderbilt University in Nashville, Tennessee, began her missive with: 'Hi my baby.
'I just to get a few things off my chest: I'm not angry and I'm glad we had a conversation earlier.'
However she then chided Belichick over her feelings of being shut out of crucial parts of his personal life.
A particular target was mom-of-three Debby, 69, who she appears to describe cryptically as 'what's her name that I'm not allowed to speak of ever' – before blasting Belichick for buying three houses with his ex that year.
'I just feel like I'm the one that loves and adores you and respects you and tries never to ask too much of you and tries to ALWAYS remind you how grateful I am of your love,' Holliday implored. But then added: 'I'm the disposable one.'
In further desperate tones, she said: 'There are so many things I'm just not allowed to talk to you about. I'm left with writing these things down because I can't verbally talk to you about it.
'You ALWAYS throw it back in my face and say 'I'm sorry you don't think that I do enough for you' and that is the end of the conversation. To answer that… you do more than enough for me for which I feel guilty for ALL the time.
'I mean, you're not married to me… you don't owe me anything. My children are not yours to take on and raise. I realize this to ALL be true!!!
'But on the other hand I see you write a check to what's her name that I'm not allowed to speak of ever and I often wonder why you feel the need to support her… (even now).
'And yet you don't ask anything from her or ask her to respect you. She just demands it.
'You purchased three properties with Debby this year and spend God knows what on the properties let alone the furnishings. And the answer that you have me is so the kids can learn how to rent them out and learn finances.'
The couple eventually split in 2023 with sources telling People they had been on the rocks for a while and the problem that led to the break-up was 'not new'.
Holliday's plea was revealed amid what is also developing into a sorry saga between herself and Hudson – who in turn is causing some of Belichick's friends to be concerned about his burgeoning latest relationship.
Additionally, former cheerleader Hudson had choice words about Holliday when she sent the photos she took of the printout to the woman on Instagram.
Screenshots of the nasty exchange obtained by the Daily Mail show Hudson launched the vicious attack by saying: ''Hey babes! Since you are tight with Ms Holiday (sic), could you please ask her what she would like me to do with this letter I found from 2015?
'Due to its pathetic and embarrassing content, I imagine she wants it back.'
Mocking 'delusional' Holliday further, she denied playing any part in their break-up.
Hudson – whose controlling antics with Belichick include a train-wreck CBS interview that went viral – wrote: 'She should make the point to burn it so she continue to live in delusional denial (that her relationship with BB wasn't doomed yeaaaaars prior to him finally dumping her.)
'I know she cares a great deal to continue to manipulate her friends, as well as the public, into believing that I came in and ruined her perfect relationship.'
Holliday would not give a comment to the Daily Mail when asked about the letter and Hudson's views. Hudson has also declined to comment.
Meanwhile, the pair reportedly clashed on exclusive Nantucket, where Holliday remains a stalwart on the island's social scene and enjoys a $4.8million home bought by Belichick. She also has a $4.2million spread in Jupiter, Florida.
TMZ said she asked organizers of a Christmas party on the island last year to remove Hudson from the venue because her daughters Ashley and Kat were the DJs – and her presence was 'inappropriate'.
Holliday was later seen on security video 'confronting' Hudson in the middle of the dance floor according to documents, added the outlet. Hudson was reported to have left as the event was nearing its end.
Hudson and Belichick have caused a storm since their relationship was revealed in 2024, following their first meeting on a flight to Florida in 2021. They reportedly stayed in touch and got together after he split from Holliday.
The most dramatic example has been of the astonishing gatecrashing of Belichick's interview with CBS in April, intended as a showpiece moment to plug his book, The Art of Winning: Lessons from My Life in Football.
The coach meekly accepted Hudson's interventions from the sidelines as host Tony Dokoupil tried to make headway. At one point she refused to let Belichick answer a question about how they first met. It was also reported she stormed out of the room and delayed filming for 30 minutes.
A string of other sensational incidents have also emerged, threatening to overshadow Belichick's first season in charge at UNC.
In one, Hudson made a startling appearance at a North Carolina practice session. Talking with her lover on the field, she looked dramatically – and out of place – glam in a white turtleneck top, snakeskin printed minted miniskirt with matching trench coat and white boots.
Prior to that, it was reported Belichick had requested Hudson be copied in on all UNC emails sent his way,
Such was the impact of her presence on the field, that a Tar Heels blog of sports site SB Nation had the headline: 'UNC is reportedly concerned about Jordon Hudson's involvement with the program.'
In an attempt to stifle such talk, newly-leaked emails by Belichick to a UNC official reveal him writing: 'Jordon has zero involvement in the UNC football program, beyond the degree that my personal media intersects with it.'
However, they also reportedly also reveal the extent of her involvement in his media relationships, partially explaining the CBS debacle.
In one email obtained by WRAL, he is reportedly wrote: 'Jordon and I have both a personal & professional relationship. This is not a secret. Jordon assists me with my personal media, which is why I asked UNC to forward media requests (eg. CBS 60 Minutes) to her.'
He also defended Hudson's refusal to let the book interview stray into personal matters – and additionally confirmed their first meeting was four years ago.
'I met Jordon randomly on a flight to Palm Beach in 2021,' he wrote. 'That is no secret. Jordon was not dodging the specific question regarding how we met, but rather was preventing the interview from continuing to probe into personal matters.
He also said CBS 'secretly had a camera focused on Jordon'.