James Middleton's Messiest Moments

It's hard to imagine that there was ever a time when Catherine, Princess of Wales' brother, James Middleton, was considered the wild child of their family. By all accounts, he seems to be a laidback lad who lives a quiet life on his farm with James' wife, Alizee Thevenet, their son Inigo, and most importantly, his beloved dogs. Additionally, James has always shared a close relationship with his eldest sister, Kate Middleton. In fact, royal expert Neil Sean once claimed in a YouTube video that James might just be her most trusted advisor. The expert proclaimed that while the Princess of Wales undoubtedly opens her heart to her husband, William, Prince of Wales, she understands that he generally has bigger fish to fry. 

Sean explained, "It's James, apparently, who Kate came to in these troubled times because she liked his calm and relaxing influence, and of course his very sage advice," per Express. Their bond has remained consistently strong through the years too. During a 2023 appearance on "Good Morning Britain," James gushed, "I'm extremely proud and I'm always taken aback by how much she does [...] and that continues to stay at the forefront of my mind," (via Hello! magazine). However, before James grew into the person he is now, the businessman's life was full of chaos, which arguably earned him the wild child tag. In fact, there was even a moment when Kate reportedly didn't want to be seen with him.

In a 2014 chat with The Standard, James Middleton acknowledged that he didn't cruise by in his school days due to dyslexia — a condition that he rightfully isn't ashamed of but regardless struggled with. So, he had to work extra hard to get good grades and earn a spot in the University of Edinburgh, to study environmental resources management. However, it didn't take James long to realize he had an entrepreneurial spirit that pulled him off the more traditional path and he ultimately dropped out only a year after starting his course. James confessed that his parents, Michael and Carole Middleton, weren't impressed with his decision, confirming, "[They] were very keen for me to stay. I'd done re-sits during my year out because my initial grades weren't good enough, so they saw that I'd worked harder than hard to get there." 

Nonetheless, James stuck to his guns and set out to pave his own way in the world. But first, he took a little detour to live it up. In 2012, photographer Niraj Tanna informed GQ that the youngest Middleton child partied too hard on his 21st birthday in 2008. He revealed that James was so drunk that "Michael had to literally carry [him] to his car." To make matters even messier, James supposedly tried to relieve himself on the street. A confidant even divulged that his own sister, Kate Middleton, didn't want to risk being spotted with her brother, so she left a little while after him.

Speaking to The Standard in 2012, James Middleton shared that he had a deeply rooted passion for baking because it brought back fond memories of his childhood. The ambitious entrepeneur soon started his customizable cake business, Nice Cakes. However, some of James' designs were far from heartwarming. According to the Daily Mail, several of his confectionaries could be customized with cheeky captions like "A yummy bum for squeezy fun" or downright offensive ones that shamed the receiver for their weight, for instance. Of course, you could also finish your NSFW cake with sexually explicit imagery. James stood by his product designs in a chat with the tabloid, arguing, "They are clearly intended to be humorous and are clearly not intended to cause any offense as is quite obvious." 

However, a few years later, his customizable gifting company, Boomf, reportedly took an undeniably offensive order. A 2019 Daily Mail report detailed how a former employee walked away from her job after the company created a gift box order with an anti-Semitic design. The ex-staffer flagged the highly offensive design to higher-ups, but they allegedly weren't terribly concerned about it and went ahead with the delivery as normal. To put the employee's claim to the test, a news agency requested a similarly offensive design and reportedly got exactly that. In response, a Boomf spokesperson promised that they would go through their policies with a fine-tooth comb to ensure it wouldn't happen again.

Controversies aside, James Middleton's Nice Cakes wasn't exactly a massive hit. A guest who got to taste one of his cakes at a Hello! magazine party described it to the Daily Mail as "very much like they had come from a supermarket." According to The Standard, the company didn't manage to turn a profit in its first three years in existence and finished the third with a substantial loss. Despite everything, Kate Middleton's brother remained optimistic. In 2013, he told The Telegraph that he wasn't fazed by the fact the company wasn't profitable because it was all a part of a startup's natural ebbs and flows, per E! News. Meanwhile, a family member had paid off a $25,775 business debt to keep Nice Cakes afloat. Unfortunately, James never got to enjoy the sweet taste of success with his business, as the Daily Mail reported it was shutting its doors in 2017. 

Things didn't go that well with Boomf either. Initially, James told the Daily Mail that he had earned a handsome profit in 2018. But at some point after that, everything went downhill. Despite having the financial resources of several high-profile investors, Boomf suffered a whopping £2 million loss in 2022, per The Standard. Then, in 2022, Express reported that James had sold Boomf. Notably, the company was under an eye-watering reported debt of £800,000 at the time. All these financial woes couldn't kill James' entrepreneurial spirit, though, as he started his dog food company Ella & Co, in 2020.  

Kate Middleton lived lavishly even before she married William, Prince of Wales, because of her family's considerable fortune. Naturally, her siblings, Pippa and James Middleton, also reaped the benefits of their parents' hard work. In the youngest Middleton's case, however, this also helped him get out of several sticky financial situations unscathed. In fact, in 2015, the Daily Mail reported that after regularly sustaining losses for three years, Nice Cakes' finances had dwindled to a mere £20, and James had to dig into the Middleton fortune to keep the lights on. Furthermore, the Princess of Wales's younger brother enjoyed the luxuries of a £780,000 apartment because of Michael and Carole Middleton's wealth. 

But despite all his advantages in life, James believed he only owed his success to himself. The entrepreneur stressed to The Telegraph in 2012 that he started his businesses through the backing of banks and other family members. "I've won awards for my own efforts because I am young and good in my own right," James asserted. "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." In fact, he only admitted to getting one thing from his parents: Their expertise from years of running their own party goods company, Party Pieces. Ultimately, James reasoned that, "Nothing is handed to anyone on a plate."

James Middleton's quiet life in his $2 million mansion in the countryside was disrupted when he got into a feud with his neighbor, David Alderton. Speaking to the Daily Mail in 2023, Alderton shared that he took issue with how James ran his farm, positing, "There are three barns full of old farmyard machinery, no good to anyone and it's all going on 50ft from our front door." Alderton added, "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." 

James responded to his neighbor's complaints in a statement to The Independent, noting that he couldn't understand why Alderton took offense to his practices when they were standard procedure and often even crucial for working farms. A source clarified to the publication that James' drama with his nosy neighbor started when he became a part of a group that was working to thwart Alderton's attempts to install something they believed would be an "eyesore." Kate Middleton's brother and Alderton have butted heads several times since then. 

According to James, Alderton visited his home when he and his family weren't around because a guinea fowl was supposedly creating a ruckus. He proceeded to terrify their family's house-sitter by screaming, "Shut those f***** birds up you noisy c***." James also maintained that Alderton had tried to get residents of the nearby villages to turn against the Middleton family with posters that portrayed them in a negative light.