The Shady Side Of Kate Middleton's Brother James

While James Middleton may have an idyllic life in the English countryside, he has attracted his fair share of negative attention since Kate Middleton's relationship with Prince William thrust him into the spotlight. James is the member of the strange and secretive Middleton family who shares the most personal content on social media, which he sometimes uses to expose the highly guarded privacy of the royal in-laws. For example, in a May 2020 Instagram video, he offered a brief glimpse into his pandemic life as he spent the COVID-19 lockdown with his parents, Carole and Michael.

As Kate's youngest sibling, James is also the Middleton who most often spoke to the press, primarily to promote his business ventures. He's the owner of the dog food company, James & Ella, and he launched his first book in 2024. As James tried to set himself apart from his sisters and parents, he has made a few awkward comments about them. He has also gone a bit too far in his efforts to avoid a nepo baby label, especially as it concerns to how much his family has helped him.

James also cast shame upon the family in the early days of Kate and William's marriage, when some of his drunken shenanigans made headlines. Back then, James was involved in quite a few photographic scandals that earned him notoriety as a "bad boy." Thankfully, he's matured and left his party-boy days behind. But the grown-up James who swapped London for the countryside still isn't immune to controversy.

James Middleton had plenty of drunken moments in his youth

Getting drunk and making questionable decisions — who hasn't been there? But the stakes are higher when you're the brother of the future queen of England. Just days after Kate Middleton and Prince William's wedding in April 2011, old photos of James Middleton resurfaced that showed him engaging in a series of embarrassing acts at a house party. In one, he posed nude covering his private parts; in another, he flashed his naked backside at the camera.

James had shared the pics to social media, but they leaked to the press in 2008 even though he had set his page to private. "These photos were not for the public, they were on his private Facebook profile and someone managed to get in and take them," a source told Us Weekly. At the time of the leak, attorneys for Michael and Carole Middleton reportedly asked newspapers never to republish the photos, which they obliged, according to the Daily Mail. That wasn't the first time James found himself in hot water.

Earlier that same year, James went out to celebrate his 21st birthday in a Chelsea nightclub and was photographed drunk, peeing on the street, which is illegal. Michael and Carole, once again, came to the rescue. "Michael had to literally carry James to the car. He was all over the place and couldn't stand up properly," the photographer behind the photos told GQ in 2012. The U.K. media never made the images public, but they were published in Australia. 

James Middleton once sold erotic cakes

Kate Middleton had been an official member of the royal family for less than a year when her baby brother made headlines for all the wrong reasons. In April 2012, James Middleton launched Nice Cakes, a new line under his Cake Kit Company that specialized in personalized items. Some of the designs he offered included some interesting slogans. "Scrummy boobies that make my hands happy," one cake read. Want another example? "A willy that wriggles and gives me the giggles."

James didn't understand what the uproar was about. "They are clearly intended to be humorous and are clearly not intended to cause any offense as is quite obvious," he told the Daily Mail. "The Great British public is renowned throughout the world for its sense of humor and a cake design is hardly likely to cause it to lose it. We intend to embrace that sense of humor." That embrace didn't last long. Days after the controversy, the "Naughty Section" on James' business website was nowhere to be found, Vanity Fair reported.

The youngest Middleton drew inspiration for his business after noting the interest in personalized cards. "We thought we would add to the excitement of a celebration and bring you personalized cakes," he told the Daily Mail in July 2012. But interest in James' cake — naughty or not — was short-lived. Cake Kit Company ceased operations in 2015, as did Nice Cake and its two other sister companies, Nice Wine and Nice Group London.

Inside James Middleton's feud with his neighbor

Shortly before James Middleton's wedding to Alizee Thevenet in September 2021, the couple purchased their first home near his parents in Berkshire. Everything was great until February 2023 when Middleton and Thevenet ran into issues with their 65-year-old neighbor David Alderton, according to The Independent. Alderton accused the couple of causing light and noise pollution, and he even went so far as to distribute disparaging flyers about them around the village. Middleton said his neighbor also threatened him, telling him that "things are gonna get brutal."

After Middleton and Thevenet welcomed their son, Inigo, in October 2023, they felt the need to escalate the situation with Alderton. "Police were contacted shortly after our son was born as we became increasingly concerned by the activities surrounding a neighbor," Middleton told The Independent. He also contended that Alderton had trespassed on his land multiple times, making James fear for his family's safety.

Alderton, whose property is 130 yards from Middleton's, was particularly aggrieved about what he described as questionable farming practices. "This month we have further been subjected to the unwelcome toxic and noxious ingress of fumes within our home from the clearly unsuitable machinery he uses," Alderton told the Daily Mail. Middleton had taken to farming after leaving his big-city lifestyle behind. "Living in London, you don't have community," James told the Daily Mail in 2022. It sounds like he didn't exactly find what he was looking for.

James Middleton has pointed out Kate Middleton's 'quirks'

The Middletons have largely preserved the royal family's privacy and have avoided discussing Kate Middleton's personal life. But James Middleton has occasionally let some things slip. In July 2023, James shared his pride in his sister's work but seemingly couldn't resist throwing in a little brotherly remark. "I'm extremely proud and I'm always taken aback by how much she does do ... But actually to be honest, she is my sister, so I know all of her quirks and everything," he laughed on "Good Morning Britain."

In fairness, James Middleton was discussing his mental health journey, and he quickly steered the conversation back to his dogs and their role in managing his depression. But that wasn't the only time that he addressed Kate's private life. Amid Kate Middleton's cancer diagnosis, which she revealed in March 2024, James penned a heartfelt Instagram post in her honor. "Over the years, we have climbed many mountains together. As a family, we will climb this one with you too," he captioned a childhood photo of the two together, seen above.

He was the only Middleton to do so, though The Telegraph conjectured that he wouldn't have made the post without his sister's permission. Whether that's the case is unclear, but the fact he didn't remove the post might suggest the family had no big issues with it. Middleton also frequently comments on the Prince and Princess of Wales' Instagram posts, indicating he feels comfortable offering some insight into the family.

James Middleton grew frustrated with his royal family connection

Being related to the Princess of Wales offered James Middleton a stage he was unlikely to have otherwise. But that's not how he sees it. James believes Kate Middleton's fame eclipsed his business career. "It [gets] frustrating," Middleton told TYD magazine in 2015 (via Us Weekly). "I work incredibly hard ... and aside from the fact that yes, I am the brother of someone very important, I am, at the end of the day, just James."

James also strived to show he was a businessman in his own right. "It's not just because of my family that I've been getting attention. I want to be known for my own contribution, not for being a 'relative of' — that's boring," he told The Telegraph in 2012. He frequently denied he had any help from Michael and Carole Middleton's multi-million dollar business, Party Pieces, even though he sold his cake kits through his parents' brand. 

Despite denying he received help from his parents, James was supported financially as he racked up significant debts before dissolving his company Nice Group London. According to the Daily Mail, James' parents took care of an overdraft in 2014. A year later, Nice Group London had barely $20 in the bank, and the company was reportedly being kept afloat by his family, the Daily Mail reported. At the time, James also lived in a London apartment that was worth more than $1 million. It was bought by his parents.