© Mario Testino / Art Partner Among Britain’s upper crust, five years can mean the difference between spending your childhood with your sibling or only seeing them on weekends and holidays from boarding school.
Kate Middleton liked school so much that, at the age of 9, she asked her parents if she could become a weekly boarder at St. Andrew’s Prep—which gave them pause because the family of five, Michael and Carole Middleton and their three children, Kate, 8-year-old Pippa and 4-year-old James, were such a tight-knit bunch.
“The Middletons were an exceptionally close family,” royal biographer Katie Nicholl wrote in her 2013 book Kate: The Future Queen, “and Carole and Mike enjoyed the vibrancy of their children, the stories and noise and laughter.”
They ate dinner together every weeknight, with the kids helping to set and clear the table. When the children were little they usually stayed close to home for vacation, sailing in Norfolk, hiking and picnicking in the Berkshire countryside, or renting an old cottage in the Lake District where the active family would rough it with no electricity or running water. (Later, skiing in the French Alps and trips to tropical islands were more like it.) But Kate did indeed join the live-in crowd at school, as did Pippa, so they were both spending at least five days away from the family homestead, leaving little James the master of the house.
Dave M. Benett/Getty Images The sisters couldn’t help but flock together more often—they had been in the same St. Andrew’s Brownie troop, and at school they both played sports and learned piano and flute. Even when Pippa proved the more accomplished athlete and student, Kate was her biggest fan.
“They had such drive and were very competitive, particularly Pippa, but never against each other,” Denise Allford, who coached the girls in sports, told Nicholl. “They were very much a team.”
And though Kate much preferred field hockey to anything taking place in the classroom, both she and her sister got along well with their teachers.
James followed at St. Andrew’s, and all three siblings were in school plays and attended summer drama camp together. Meanwhile, the competitive fire ran through the whole family, which—Prince William later learned—loved to play games and tease each other during holidays together. On Christmas morning, after Kate, Pippa and James had upended their stockings, the family always started on a puzzle, an annual tradition.
“The whole family are mad about tennis and they hate losing,” a family friend told British GQ in 2012. “Carole’s brother, Gary, lost to James once, and didn’t play for years afterwards.”
Feeling uneasy about her new environs, when a 13-year-old Kate started at the Downe House School, a prestigious all girls’ academy, she chose to not be a boarder, unlike most of the girls in her year, who’d known each other since they had started at Downe when they were 11. Kate never ended up settling in and transferred to Marlborough College, once again a boarder.
Pippa ended up at Marlborough too, on a full sports scholarship, so the sisters were together once again, playing hockey and studying music. Then, when he was finished with St. Andrew’s Prep, James moved on to Marlborough as well—but Kate had graduated by then.
Antony Jones/UK Press via Getty Images The siblings’ paths diverged more thoroughly when Kate, after taking a gap year, headed to St. Andrews University in Scotland, where, as it turned out, her prince awaited.
The sisters talked at least every other day, so by Christmas of 2003, Pippa was well aware that Kate’s relationship with William was more than a friendship—enough so that Kate gave her mom the go-ahead to tell Michael, James and Carole’s own brother, Gary, over the holiday break. The next year, Pippa and James were regular visitors at Balmoral, the queen’s beloved home in Scotland, when Will and Kate would go there for weekends.
Meanwhile, Pippa, after her own year off, enrolled at the University of Edinburgh, as did James a few years later; but while Pippa graduated with a degree in English literature, James left after a year. The youngest of the Middleton siblings, who like Pippa unwittingly found himself on an international stage when their sister married the future king of England in 2011, opened up earlier this year about his struggles with dyslexia, which made school fairly unbearable for him, and his ongoing battle with depression. He was inspired to speak out, he wrote in a column for the Daily Mail, because Kate, William and Prince Harry had made mental health awareness one of their central causes with their Heads Together campaign.
Even though having Pippa around at Marlborough was a comfort, James recalled, he “didn’t fit in.” He did just well enough to get into university, but once he was there, “A month in, I thought: ‘What am I doing here?’ I couldn’t cope with independent studying and wanted to quit—and after a year I did.”
In 2007, Kate danced semi-discreetly with her sister and brother a few rows behind William and Harry at the Concert for Diana, the world not yet knowing that she and William were back together after a brief, but widely publicized, breakup.
Dan Kitwood/Getty Images While Kate didn’t face the very worst the media had to offer when she was dating William (that had been reserved for her late mother-in-law and future sister-in-law), the headlines were constant and, at times, merciless—such as when she was dubbed “Waity Katie” for hanging in there for years without a ring or, in their rougher spots, William’s full attention.
Kate’s journey, however, was leading to something—and when that something occurred, all eyes suddenly turned just enough to spy Pippa and James Middleton off to the side.
Because of who Kate’s boyfriend was, for instance, there was public interest in the fact that, on his 21st birthday in April 2008 he needed to be practically poured into the car after he and his family got the VIP treatment at London nightspot Raffles. According to Nicholl, a mortified Kate had left through a back entrance. Paparazzi saw but, warned by Prince Charles‘ office to leave Kate and her family alone as they were still technically private citizens, the British papers didn’t run with it. Australian tabloids, however, enjoyed the scoop.
Shutterstock When Kate was about to get married, the still-single James and his baking businesses—one providing do-it-yourself cake kits for home bakers (Kate helped him establish his website) and the other making personalized cakes—never faced as much speculative fascination as the still-single Pippa, her fashion choices (including her formfitting bridesmaid dress at the royal wedding) and her forays into event-planning, writing and TV presenting.
Old photos of him messing around with his mates in school and stories of his drunken partying made for salacious headlines, but on the flip side his average-dude behavior drew comparisons to Prince Harry’s schoolboy (and young-adult) antics.
But just because he was less scrutinized than his sisters didn’t mean James, who was also starting a new business at the time—his still-chugging personalized gifts company, Boomf—didn’t feel as if he too was on display to an uncomfortable degree.
“Suddenly, and very publicly, I was being judged about whether I was a success or a failure,” he recalled to Tatler this year. “That does put pressure on you. Because in my mind I’m doing this irrespective of my family and events that have happened.” (And both he and Pippa were accused of using their connections to publicize themselves—though it’s hard to see how they could have tried to advance their careers in any way and not be accused of trading on the Middleton name. Either way, it’s said that they were both advised to keep more demure profiles, with William happy to offer guidance on the subject.) James, who’s been sporting a beard now for years, was a clean-shaven lad of 24 when he gave a reading of Romans 12 at his sister’s wedding, which was only watched by about 2 billion people around the globe, in 2011. His impressive showing, which for many outside the U.K. was the first time they had really noticed Kate’s handsome brother, was considered a refreshing new start for him in the eyes of the U.K. media.
Though she called seeing the throngs of people outside Westminster Abbey on Kate’s wedding day “surreal,” Pippa said on Today in 2014, “It sounds funny to say, but we saw it as just a family wedding. And actually, I didn’t realize, perhaps, the scale of it until afterwards.”
The attention paid to her dress, and the shape of her in it, that day was “flattering” but “embarrassing,” she added, because the simple design was meant to make the overall look “insignificant” in comparison to the bride’s Sarah Burton gown.
“It has been difficult, I suppose, going from a very normal life to sort of managing everything that happened after the wedding,” Pippa also said about what started out as fame-by-association but had since evolved into her own public profile. “I’ve had amazing opportunities,” she added. “I feel very fortunate to have opportunities and sort of access to things that maybe I wouldn’t necessarily.” At the same time, however, “It’s hard sometimes, but I have felt publicly bullied a little bit just by, you know, when I read things that clearly aren’t true or that, whichever way someone looks at it, it’s a negative side. It is quite difficult. Because eventually I’m just paving my way and trying to live a life like any 30-year-old.” James, meanwhile, felt caught between a rock and a hard place, in that he didn’t like the scrutiny from the fame-by-association, or, simultaneously, the fact that his sisters had always cast a long shadow and it hadn’t been easy to carve out his own individual space apart from them, even when the Middleton name wasn’t famous.
“It’s always been, whether at school or now, that I am Pippa and Catherine’s little brother,” he told the Daily Mail in 2015. “It’s probably going to be the story of my life. [But] I am James Middleton. I am very proud to be ‘the little brother of…,’ but, equally, they are proud that I am who I am.”
There were hangers-on and others with nefarious motives who might try to latch on because his name is Middleton, but “when somebody is interested in me for other reasons, I can spot it a mile off,” he added. “All I want to do in my life is be known as me and for what I do.”
And youthful faux pas aside, James was loyal to Kate and Pippa and protective of their privacy, explaining to British GQ in 2012 that he was happy to chat—a media presence was important to run a successful business—but he would never betray his family’s confidence.
John Stillwell/PA Wire/Press Association via AP Images When she got engaged to Prince William and then joined the royal family, Kate’s life was automatically swallowed up by the traditions practiced by her in-laws, but she has stayed close to her family, needing that BFF support from Pippa and gladly taking her parents up on babysitting offers once she became a mum. Most years, William and Kate (and now all the kids) vacation in Mustique with Carole and Michael to relax on the private island’s picture-perfect beaches, and they spent two weeks there in June.
The Middleton siblings haven’t missed a christening, either, the family reliably gathering for the baptisms of Prince George, Princess Charlotte and Prince Louis, and overall the family has spent plenty of time over the years rubbing elbows with VIP guests at Buckingham Palace and other spots where the House of Windsor might be entertaining.
The most noticeable difference in Kate, Pippa and James’ relationship is that Kate rarely gets to be right next to her siblings or parents anymore, at least as far as press and formal portraits released to the public go. But we’re guessing that there’s a cloud full of snapshots taken at holidays and other private family gatherings to fill in those gaps in the album.
Karwai Tang/Getty Images Pippa and James, however, regularly arrive at weddings and other outings together, and they kept up their sporting ways, paddleboarding and playing tennis on vacation and competing in events such as the ÖTILLÖ Swimrun World Championship—6.1 miles of swimming and 40 miles of running, split between teammates—and a London-to-Brighton bike ride for the British Heart Foundation in 2015.
The whole lot of them are also regulars at Wimbledon every summer, with Pippa going on different days this year, once with her husband, brother and parents, and again to sit in the royal box with Kate and Meghan Markle.
Not that there haven’t been rumors of a rift between James and Kate, since they’re rarely seen spending time together outside of milestone events, unlike Kate and Pippa. But reminiscent of the concerns that Harry and William were feuding because Harry wanted to have his own foundation with his wife instead of his brother, it’s mainly only because James is a grown man who is out doing his own thing. “I lead a separate life to them,” he told Tatler. “If there’s interest in me, great. If there’s interest in me because of them, that’s different.”
Moreover, James has been on a very different journey than either of his sisters, and though he was doing the usual stuff—work, dating, royal weddings, etc.—he had a lot to grapple with, and for a time he was keeping it all to himself.
Also in the Daily Mail in January, James revealed that he was diagnosed with an irregular heartbeat in late 2016, brought on by stress and anxiety. “The best part of 2017 passed in a fog,” he wrote. “I barely functioned, stopped talking to my friends, went through the motions of living and working but achieved nothing at all.”
Similar to how Prince Harry talked in 2017 about pushing his issues to the side for years and refusing repeated offers of help from William until, one day, he was ready to seek treatment, James told Tatler that when his depression and anxiety was at its worst, “I shut myself off, I didn’t communicate with my family at all. But there’s only so long you can hold your breath.”
James Gourley/REX/Shutterstock “You may wonder why I didn’t confide in them,” he wrote for the Mail, “but those who are closest to you are the hardest to speak to. It was impossible to let my loved ones know about the torture in my mind. Equally, anything they’d have said would have been rebuffed.
“That’s why I withdrew from them, repelled their well-intentioned advice and finally stopped answering their calls and texts.”
James eventually started therapy and in the beginning of 2018 he took a break from his business and went to stay at Glen Affric, the Scottish estate belonging to the family of Pippa’s husband, James Matthewsalsoa longtime friend of her James Middleton’s (and his partner in the 2015 Swimrun). Pippa and Matthews had married in May 2017 with the whole family, including myriad royals, in attendance. While James was there he occasionally played host, prompting reports that he was working as a “hotel tour guide,” which understandably annoyed him. “I don’t stand around with a little flag pointing out where William Wallace was last seen,” he cracked to Tatler.
The now 32-year-old entrepreneur also recently shared with the Telegraph that his whole family came to some of his therapy sessions, including Kate.
“The fact is, no matter what experience someone has, your family members are the hardest people [to talk to about it],” he said. James also has five dogs now—his Cocker Spaniel Ella, who’s been with him the longest and is the mother of Kate and William’s dog, Lupo, as well as Inca, Luna, Zulu and Mabel—and he has credited them extensively for helping him get through that dark time, when he could barely eat or sleep and couldn’t even concentrate enough to watch a movie or read a book.
Listening to Harry Potter audiobooks read by Stephen Fry wasa comfort, he said.
Even more of a sign that he’s healthier and happier than ever: James confirmed this month that he was engaged to Alizee Thevenet, a French financial analyst who he met in a bar. The couple vacationed with his parents, Pippa’s family, and Matthews’ brother Spencer and his wife in St. Barts in January. Alizee was also James’ date to Lady Gabriella Windsor‘s wedding in May.
Instagram / James Middleton “I have two lovely sons-in-law and I hope I’ll have a lovely daughter-in-law,” Carole Middleton said in a rarer-than-rare interview with the Telegraph last December, though at the time James and Alizee hadn’t taken their romance fully public.
In his post for the Mail, James also acknowledged that he had the platform he did thanks to his sister, William’s future queen, and he wanted to use that visibility to draw attention to the causes that mattered to him.
“People have asked me, too, if my public profile has made it harder for me,” he wrote. “Would I have become so depressed if I hadn’t been subject to the pressure of public scrutiny that comes with my association with the Royal Family?
“The answer is, I believe I would. But I wouldn’t have found a voice or an outlet for my story if it hadn’t been for the people I’m related to.”