There are two wedding anniversaries happening this week: the Duke and Duchess of Sussex’s eighth wedding anniversary (today), and Pippa Middleton and Terribly Moderately Wealthy James Matthews’ ninth wedding anniversary (tomorrow). Pippa and TMW James married quickly after they started dating, although they had been circling each other for years. The British tabloids always made it sound like TMW James was obsessed with Pippa for years, while she merely settled for him after her big push to marry a titled aristocrat crashed and burned. Still, it’s become a good marriage for her and she seems much happier than her sister. Here are some highlights from The Mail Remembers: Pippa and TMW James’ Origin Story.
When Pippa Middleton married nine years ago in May, it was the culmination of James Matthews’s reported 10-year pursuit to win her over. But perhaps Pippa and the hedge fund manager, now 50, may never have even crossed paths if it weren’t for the ‘ruthless’ nature and determination of the Princess of Wales’s sister. At least that’s the opinion of Sunday Times bestselling author and royal biographer Tina Brown, who detailed Pippa’s rise in her book The Palace Papers.
‘Pippa’s social ascent seems more calculated than Kate’s,’ said Brown, who claims her nature was evident from her student days. ‘At Edinburgh University, she shared an apartment with two boys whose fathers were dukes.’ An alum told the biographer: ‘As soon as Pippa arrived at Edinburgh, she was assiduous about joining the right social circle. She was very charming about it, but quite ruthless in cultivating the ‘right friends,’ Brown added.
Pippa’s romantic quest concluded with billionaire hedge fund manager James, heir to the Scottish feudal title of Laird of Glen Affric and son of Eden Rock Hotel owners, David and James Matthews, who was, according to sources, always had his eye on Pippa. In 2016, the Mail on Sunday revealed that their tryst involved a decade of waiting, meticulous planning – and a dazzling campaign of gifts and treats that extended to her parents, too.
Thanks to the millions earned from Eden Rock Capital Management, the financial company named after his parents’ Caribbean hotel, James was in a position to woo Pippa in the most extraordinary style. It turned out that even before they became an ‘item’, James had flown the whole Middleton clan to St Barths and his parents’ hotel. They travelled on his £3 million private jet.
In 2016, the Mail on Sunday revealed that James had been patiently pursuing his bride-to-be for a full ten years – strategically planning his advances while waiting for Pippa to outgrow the eight-year age gap between them. And while other privileged young men might busy themselves with a series of girlfriends, James used the time to build a business and a fortune so vast he could treat her like a princess. Friends say he knew Pippa was the one from the moment she set foot on St Barth’s and confidently introduced herself to him. But with Pippa taken and an eight-year age gap between them, James was forced to bide his time.
Though he always stayed in contact, he had to watch from afar for six long years as Pippa finished her university studies and wrapped up relationships with two serious boyfriends, banker JJ Jardine-Paterson and cricketer Alex Loudon.
Yeah, I’ll talk sh-t about the Middleton family, but Pippa seems to have a good marriage and she seems happy, so good for her. TMW James seems to support her in every way, and they have three children and live a somewhat quiet life. Of course, I’ve always had my doubts about James’ wealth – I believe he’s a millionaire, for sure, but the Middletons always promoted him as “terribly rich” and/or a possible “billionaire.” I think he and Pippa live quite comfortably, but if he was truly rolling in money, he and Pippa probably wouldn’t be involved in all of these petty disputes and scandals in and around Berkshire. Scandals like Pippa’s foray into running a petting-zoo business, which they just sold because it was drowning in debt. Petty disputes like their years-long campaign to shut down a public-use trail which cuts through their property.
Speaking of that footpath drama, the Daily Mail recently had a piece where they quoted Pippa and James’ neighbors at length over the closing of the footpath. One resident said: “They’re not even the proper Royal Family.” LOL. A local councillor named Tony Vickers said: “The path has been used for generations but money talks. The Middletons are not well connected with the community. There’s a sense they’re splitting the community. There are a number of very wealthy anti-ramblers but ordinary people and people who like walking would like to see it open.” Another resident said: “We have so many famous people living around here – footballers, other celebrities, they don’t make a fuss. They come here to live in peace, like we all do. Apart from the Middletons.” Pippa and TMW James are really tearing the community apart. Tacky, nouveau-riche drama. Just what I’d expect from the Middletons.
Photos courtesy of Cover Images.
- USA Rights Only – London, UK -5/20/17-The Wedding of the Duchess of Cambridge’s sister Pippa Middleton at St Mark’s Church -PICTURED: Prince George, Pippa Middleton, James Matthews, Catherine Duchess of Cambridge -PHOTO by: PA Images/INSTARimages.com -31379309.jpg Editorial Rights Managed Image – Please contact www.INSTARimages.com for licensing fee and rights: North America Inquiries: email sales@instarimages.com or call 212.414.0207 – UK Inquiries: email ben@instarimages.com or call + 7715 698 715 – Australia Inquiries: email sarah@instarimages.com.au Êor call +02 9660 0500 Ð for any other Country, please email sales@instarimages.com. ÊImage or video may not be published in any way that is or might be deemed defamatory, libelous, pornographic, or obscene / Please consult our sales department for any clarification or question you may have – http://www.INSTARimages.com reserves the right to pursue unauthorized users of this image or video. If you are in violation of our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image or video, and where appropriate, the cost of collection and/or statutory damage. Featuring: Prince George, Pippa Middleton, James Matthews, Catherine Duchess of Cambridge Where: London, England, United Kingdom When: 20 May 2017 Credit: PA Images/INSTARimages.com **USA Rights Only**
- USA Rights Only – London, UK -5/20/17-The Wedding of the Duchess of Cambridge’s sister Pippa Middleton at St Mark’s Church -PICTURED: James Matthews and Pippa Middleton -PHOTO by: PA Images/INSTARimages.com -31379864.jpg Editorial Rights Managed Image – Please contact www.INSTARimages.com for licensing fee and rights: North America Inquiries: email sales@instarimages.com or call 212.414.0207 – UK Inquiries: email ben@instarimages.com or call + 7715 698 715 – Australia Inquiries: email sarah@instarimages.com.au Êor call +02 9660 0500 Ð for any other Country, please email sales@instarimages.com. ÊImage or video may not be published in any way that is or might be deemed defamatory, libelous, pornographic, or obscene / Please consult our sales department for any clarification or question you may have – http://www.INSTARimages.com reserves the right to pursue unauthorized users of this image or video. If you are in violation of our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image or video, and where appropriate, the cost of collection and/or statutory damage. Featuring: James Matthews and Pippa Middleton Where: London, England, United Kingdom When: 20 May 2017 Credit: PA Images/INSTARimages.com **USA Rights Only**
- USA Rights Only, London, England – 5/20/17-The Wedding of the Duchess of Cambridge’s sister Pippa Middleton at St Mark’s Church -PICTURED: James Matthews and Pippa Middleton -PHOTO by: PA Images/INSTARimages.com -31381337 Editorial Rights Managed Image – Please contact www.INSTARimages.com for licensing fee and rights: North America Inquiries: email sales@instarimages.com or call 212.414.0207 – UK Inquiries: email ben@instarimages.com or call + 7715 698 715 – Australia Inquiries: email sarah@instarimages.com.au  or call +02 9660 0500 – for any other Country, please email sales@instarimages.com.  Image or video may not be published in any way that is or might be deemed defamatory, libelous, pornographic, or obscene / Please consult our sales department for any clarification or question you may have – http://www.INSTARimages.com reserves the right to pursue unauthorized users of this image or video. If you are in violation of our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image or video, and where appropriate, the cost of collection and/or statutory damage. Featuring: James Matthews and Pippa Middleton Where: Englefield, England, United Kingdom When: 20 May 2017 Credit: PA Images/INSTARimages.com **USA Rights Only**
- USA Rights Only – London, UK -5/20/17-The Wedding of the Duchess of Cambridge’s sister Pippa Middleton at St Mark’s Church -PICTURED: Pippa Middleton, Catherine Duchess of Cambridge -PHOTO by: PA Images/INSTARimages.com -31379325.jpg Editorial Rights Managed Image – Please contact www.INSTARimages.com for licensing fee and rights: North America Inquiries: email sales@instarimages.com or call 212.414.0207 – UK Inquiries: email ben@instarimages.com or call + 7715 698 715 – Australia Inquiries: email sarah@instarimages.com.au or call +02 9660 0500 – for any other Country, please email sales@instarimages.com. Image or video may not be published in any way that is or might be deemed defamatory, libelous, pornographic, or obscene / Please consult our sales department for any clarification or question you may have – http://www.INSTARimages.com reserves the right to pursue unauthorized users of this image or video. If you are in violation of our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image or video, and where appropriate, the cost of collection and/or statutory damage. Featuring: Pippa Middleton, Catherine Duchess of Cambridge Where: London, England, United Kingdom When: 20 May 2017 Credit: PA Images/INSTARimages.com **USA Rights Only**
- North America, Australia and New Zealand Rights Only – Paris, France -20180527- Celebrities at Roland Garros Day One -PICTURED: Pippa Middleton and James Matthews -PHOTO by: INSTARimages.com This is an editorial, rights-managed image. Please contact Instar Images LLC for licensing fee and rights information at sales@instarimages.com or call +1 212 414 0207 This image may not be published in any way that is, or might be deemed to be, defamatory, libelous, pornographic, or obscene. Please consult our sales department for any clarification needed prior to publication and use. Instar Images LLC reserves the right to pursue unauthorized users of this material. If you are in violation of our intellectual property rights or copyright you may be liable for damages, loss of income, any profits you derive from the unauthorized use of this material and, where appropriate, the cost of collection and/or any statutory damages awarded Featuring: Pippa Middleton and James Matthews Where: Paris, France, France When: 27 May 2018 Credit: INSTARimages.com **North America, Australia and New Zealand Rights Only**


















They are conflating the “reporting” about Pippa’s pre James days at Edinburgh with her settling for a series of non titled men. James was also in a long term relationship with his assistant for much of the “ten years” he allegedly was plotting to be with Pippa. I also remember this originally being reported as essentially Carole Middleton’s fantasies about how they got together and how she kept pushing him on Pippa. The source on this piece could not more obviously be Carole or a PR rep for the Middletons.
Pippa certainly had more serious boyfriends then the ones quoted in the Mail article. She dated at least two hedge fund bros after Kate married. I remember she was dating a guy who moved to, I think, Switzerland.
“Outgrow the 8 year age difference “ 🙄 Should there be kudos for this or like wtaf? I get why it had to be Pippa for her royal connection to help legitimize his family’s purchased title but that’s actually super creepy, especially if it’s true he wasn’t dating other women, or not seriously. These people are so weird. It’s the g-d 21st century. Can’t y’all just be happy being rich?
i think it was a really creepy comment but it also doesnt entirely make sense. If they got married 9 years ago, Pippa would have been 33, and if they met when she was around 23-24, and he was 31 or so, that’s not a terrible age gap. It’s not like they met when she was 10 and he was 18 and he was waiting around for her to turn 18 or something. that would be super creepy.
This article is so creepy. It makes James sound like a groomer.
PSA: Flesh tone is not an ideal choice in attire, especially when the bosom is constructed to resemble saggy breasts. Thank you.
Kate was cosplaying grandmother of the bride in that get-up.
My thoughts exactly. Keen’s bustline is so saggy in that pink dress. Oh, why won’t the royal women buy proper undergarments?
This style of dress typically makes me think of one particular term for a bra – over the shoulder boulder holder.
Very hard to do it right and this is definitely not one of the rare successes.
I absolutely despise Kate’s dress from Pippa’s wedding. Why was the chest so saggy?? It’s awful looking. Plus the color was not flattering.
I think Pippa has the life Kate wanted.
How dare women have goals in life and not stay excactly where they are. But men…. Yes men can work their way up. Lol. The misogyny is flabbergasting. The anti woman stories are the backlash to the strong feminist movement. First they try to make Meghan look bad because she works, now its Pippa socialising and then Emma who must be pitted against Meghan. I honestly can’t stand this women hating bs anymore.
I hear you but it’s not all in the same bucket. Some outrageously sexist stories have been printed about Pippa, it’s true. She was young and hot and played the field. No judgment. But wasting a prestigious education on finding a rich husband rather than building self-sufficiency also shouldn’t be applauded.
Megan did exactly that. She worked hard and has always had the ability to take care of herself. That’s the example we need to set for young woman.
@migghtmolly, and this is ALSO feminism. If that was pippas choice, its hers and its absolutely ok! Feminists do not look down on other women because they don’t fulfill our expectations. Selective feminism is not it.
I already said I celebrate her choice to date around. I did it too. I love the freedom women have now. But do you consider the sitcom Keeping Up Appearances sexist? Pride and Prejudice, is that sexiest? No because critiquing shameless social climbing isn’t sexist.
Every time I see a photo of her husband I am fascinated by how he looks like he was put in an medieval stretching rack.. pippa closes walking paths that have been used longer than she has been alive while her sister is confiscating park land I bet these two didn’t share their toys as children also.
Hmmm. Tina Brown saying that Pippa’s social ascent was more calculated than Kate’s? Are we just glossing over the switching of schools from Edinburgh to St. Andrew’s and the gap year, copying William’s moves? I’m just saying.
That made me laugh too. I do think Pippa was very calculated n her choices – especially bc by that point, Kate was dating William (I think the timing is right.) So Pippa would have felt pressure to at least get a duke. She and George Percy seemed to be good friends for a while but I dont think they ever dated and I doubt he would have married her given his family and title.
But either way – Kate was calculated too. Even more so in my opinion bc I think she was making choices at Marlborough (or even before then) to get into William’s circle.
I liked Pippa’s gown. But Kate’s get-up? Sheesh. It’s tragic.
And warning to the TMW couple: Mess with the ramblers and you get the thorns lol.
I absolutely believe James is a millionaire. Unless she was completely duped, Carole Middleton would not settle for anything less for Pippa.
Pippa’s life was a lot more normal than Kate’s was, as far as dating different people, working different jobs, not being tied down, (not being a stalker), just being unattached for a while till things fell into place. I always got the impression she was the one person in the family that you’d probably be able to relate to, easily.
I think the papers are going free Pippa right now because they can’t go after Kate. Pippa was ruthlessly ambitious! She lived with the sons of dukes! She wanted to marry wealthy!
But then they say that Kate wasn’t a gold digger… how is living with the heir to the throne less ambitious than living with the sons of dukes?
I also wonder why George Percy and Pippa didnt get married – they seemed to have been great friends, and Pips could have had a comfortable marriage if not th most passionate one.