Inside the special sibling bond between the Princess of Wales and her brother

It was a promise made at a hospital bedside − to climb a mountain together.

And when James Middleton and his sister Catherine did just that a little over two weeks ago, the world got a glimpse of the bond between the future queen and her younger brother.

While the world had long known how close knit the Middleton family was − something that apparently appealed to Prince William way back when he and Catherine first started dating − it was Pippa who stole the limelight in the early days.

But in recent years, it has become increasingly clear that James and Catherine share a particularly beautiful bond − one that was born from unimaginable challenges for both.

Early life

James Middleton was born on April 15, 1987 − five years after his sister Catherine, and four years after middle child Pippa.

Unlike Catherine, who spent two years of her early life in Jordan, James was raised wholly in Berkshire, in England’s south-east, where Middleton still lives in a country farmhouse in Bucklebury, close to the family home, while Catherine lives about 40 minutes away at Forest Lodge in the region’s historic town of Windsor.

During a 2025 interview with Hello!, Middleton touched on his special bond with Catherine.

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“I jokingly say that I had three mothers growing up. I had my mother and my two sisters, who were mothering figures to me,” he said.

“I was very fortunate. 

“We had a fantastic childhood, and they included me in everything they did, and still do. I’m now in my late 30s and we still have that friendship.”

That same year, Middleton told The Sunday Times, the childhood was punctuated by family driving holidays where they would indulge their love of hiking − and rather tellingly − climbing mountains together.

“Holidays tended to be packing up the car and driving somewhere,” he said. 

“My parents, sisters and I would visit different places in the Swiss Alps each summer, such as Les Masses, or we’d go to Avoriaz in France.

“Dad would find a mountain refuge where we’d have a rather sloppy soup-like meal for tea, but we were so hungry from a day of hiking that it tasted amazing.

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“Then we would fall fast asleep in our bunk − we’d sleep on one long bunk, all five of us − surrounded by other walkers. 

“The next day we’d wake up early, put our walking boots back on and continue our trek, ending up in another village.”

He even revealed a recent trip to the French Alps with his wife and young son had stirred up memories of his childhood.

“It was a pinch-me moment that brought me back to childhood summers when I’d hike up mountains with a rucksack that was bigger than me,” he said.

School years

Middleton followed in Catherine’s footsteps, attending St Andrew’s School, in Berkshire, and later Marlborough College.

But school was not easy for him, and he was diagnosed with dyslexia at the age of 11.

He told the Daily Mail in 2011, the diagnosis brought “some relief” after years of trying to hide his struggles.

Despite being taken under the wing of his older sister during the brief time they were both there, he found his years at Marlborough College particularly difficult.

“Spelling and reading are something you’re expected to be able to do by then, so if you struggle at them, it’s not the easiest,” he said.

“I even had a little rhyme to learn how to spell Marlborough as my father said I would never get in if I couldn’t even spell the name of the school.”

Catherine finished school and after a gap year, headed to St Andrews University, where she met her prince.

Meanwhile, Middleton failed his final school exams.

“I had very capable sisters who had succeeded in exams, then I came along and naturally my parents didn’t know what to do, because I applied myself really well to work, and they fully were expecting me to go to university.”

He eventually managed to win a spot at Edinburgh University and studied environmental resources management for one year in 2006 before dropping out.

Press intrusion

The following year, he launched his first business venture, The Cake Kit Company, which sold themed baking kits and custom cakes, some of which was distributed by his parents’ former party supply business, Party Pieces.

But as he built his business, Middleton became a target of the British press over his antics, including stumbling out of a nightclub and urinating in the street after his 21st birthday party.

Middleton told Tatler in 2019 that when it became public in 2003 that his sister was dating the future king, his whole family was thrust into the limelight. It was particularly difficult for James, who was just 17 at the time.

“Suddenly, and very publicly, I was being judged about whether I was a success or a failure,” he said. 

“That does put pressure on you because in my mind I’m doing this irrespective of my family and events that have happened.”

Royal wedding jitters

The pressure intensified when he was given the job of delivering the only reading at the couple’s 2011 royal wedding ceremony.

Despite his nerves and fears that he would flub the reading, the trust placed in him by his adored sister and soon-to-be-brother-in-law paid off with a flawless delivery.

Soon after the wedding, it was James who gifted Catherine and William their beloved dog Lupo, who was the offspring of his own pet, Ella, whom he would go on to write about in his memoir.

But there would be more battles around the corner.

The Cake Kit Company and Middleton ended up winning a number of awards, and led to three more business name registrations; Nice Cakes, Nice Wine and Nice Group London; before the business ultimately folded in 2015.

The following year, Middleton felt the first signs of the depression he would go on to battle, first in private, and later publicly.

Battle with depression

He eventually divulged his mental health battles in an opinion piece he wrote for the Daily Mail in 2019, during which he also revealed he had been receiving treatment at that point for a year for ADHD and depression, which at times left him feeling suicidal.

He said he was inspired to go public, in part, because of Catherine and William, who along with Prince Harry, launched their Heads Together mental health campaign in 2016.

In his 2024 memoir, Meet Ella: The Dog Who Saved My Life, Middleton revealed Catherine was one of his biggest supporters.

While his parents were of a generation where mental health was rarely discussed, Catherine and William had already paved the way for honest conversations, while Catherine also attended treatment sessions with her brother.

“They come to a session with me, and the fact that they are here, wanting to help me, makes me burst into tears,” he wrote in his book.

“Catherine has already done a lot of work through her mental health initiative Heads Together, and she asks [my doctor] some pertinent questions.

“She understands so much. I’m overwhelmed. I feel such gratitude and admiration for her, for her knowledge and compassion.”

Grateful for his sisters 

As recently as 2025, he told The Mirror how grateful he was for Catherine and Pippa.

“I’m incredibly fortunate to have my two sisters, not just as siblings, but as friends,” he said.

“They’ve seen me at my best and at my lowest, and they’ve always been there when I’ve needed them.

“Sibling love is something unique, you can’t choose your siblings, it can be complicated, it takes work, but when it’s strong, I believe it’s one of the most powerful bonds there is.”  

That same year, he told Hello!, ”We’re a close family, and we’re fortunate in that we see lots of each other. 

“We’ve been brought up knowing that you can’t take family for granted

“You don’t get to choose them, as you can choose your friends. But I don’t think you can give up on your family like you can sometimes with friends.”

Climbing mountains together

In early 2024, it was Middleton’s turn to support his eldest sister during her toughest battle − cancer.

The Princess of Wales had already undergone major abdominal surgery in January of that year when speculation led her to film a video announcing she was undergoing “preventative chemotherapy” after cancer had been found to be present.

When news first broke, Middleton took to his Instagram account in a show of public support for his sister.

“Over the years, we have climbed many mountains together,” he wrote alongside a photo of himself and Catherine wearing matching red backpacks from what appeared to be the top of a hill.

“As a family we will climb this one with you.”

Then, two weeks ago, came the news that Catherine had completed the gruelling National Three Peaks Challenge over the weekend of June 27–28.

While early reports suggested Catherine had made the journey alone, it was soon revealed Middleton had joined her on the challenge, which involves scaling three of the UK’s highest peaks, scattered across three countries, in just 24 hours.

Not only that, but a video posted by a fellow participant later showed the princess walking down the final descent while holding the hand of her younger brother, who was behind her.

Days after completing the journey, Middleton took to Instagram with his own post.

“I’m so incredibly proud of my darling sister,” he wrote. 

“Two years ago, I told you we’d climb this mountain together. 

“We talked about climbing mountains while you were in hospital, and about the incredible healing power that nature can have for both the body and the mind. 

“So it was such an honour to join you for your Three Peaks Challenge for the Royal Marsden Cancer Charity.

“Seeing how far you’ve come is nothing short of inspiring. Your strength, resilience and determination, all while being the most amazing mother, wife, daughter and sister, inspire me and so many others every single day.

“Keep being exactly who you are.”

His post was liked by the official Instagram account of the Prince and Princess of Wales.

Royal commentator Victoria Arbiter told nine.com.au recently the symbolism of Middleton joining his sister on the challenge was not lost on her.

“The symbolism there is wonderful, and he has been very open about his mental health battles, and I think the fact that Catherine and he went and climbed this mountain together, metaphorically, symbolically, whatever you want to call it, that they did this together, speaks volumes about that family connection.”

It is no doubt a connection Catherine will continue to rely on in the days and years ahead.