Middleton, Kardashian and Gerber: living in the shadow of successful sisters

Life can be hard when your siblings are supermodels, billionaires and future Queen Consorts

Presley Gerber, Rob Kardashian and James Middleton have all struggled to reach the success of their female siblings. 

It used to be that brothers and sisters fought over who got to sit in the front seat of the car or who had the bigger scoop of ice cream.

But when your sister has 187 million more Instagram followers than you, married a future king or fitted into your famous family in a way that you weren’t quite able to, it’s understandable why you might suffer in the shadow of their success.

Then factor in the fact that everything your celebrity sister does is heavily documented on social media, with fan accounts and in the press in a way that your life isn’t, and the stakes are instantly higher as you figure out your place in their world.

Here, we look at why Rob Kardashian, James Middleton and Cindy Crawford’s son Presley Gerber have publicly struggled to reach the heights scaled by their more famous and successful sisters.

Rob Kardashian

Rob Kardashian, 33, has had a difficult relationship with his famous family, and it has been well documented throughout the 14 years Keeping Up with the Kardashians has been on air. As the only boy in the family of five girls, Rob's levels of fame or success haven't come close to what sisters Kim, Kylie and co have achieved, and the former sock salesman has often found himself estranged from his sisters and has also been embroiled in a messy custody battle over his daughter, Dream.

Worth about Dh36 million, thanks to money he made from the show and various personal appearances throughout the years, Rob's wealth doesn't come close to Kim and Kylie's Dh3.3 billion, Khloe's Dh146m, Kourtney's Dh128m or Kendall's Dh110m fortunes, and in 2018, his mother Kris was forced to bailout his failing sock brand, Arthur George, by buying a 50 per cent stake.

‘No father figure… No guidance’

Rob’s father, OJ Simpson’s defence lawyer, Robert Kardashian, passed away when Rob was 16.

Attributing her brother's issues to the lack of father figure in his life, sister Khloe said, "When Bruce [Jenner] was around, he was great, but he was going through his own things that none of us understood at the time. Lamar was [Rob's father figure]. Once Lamar left … I think Rob didn't know where to go. He was like, 'I don't have guidance anymore.'"

Rob began to publicly break away from his family back in 2013 when a 45kg (100 pound) weight gain saw him bail on sister Kim’s wedding to Kanye West at the last minute.

"I was doing suit fittings in Paris right before the wedding and I just wasn't comfortable. I'm 6'1" and at my most I probably weighed 300lbs," he later told People. "There were cameras at the airport on our trip there and I was very unhappy with the person I saw in all the pictures."

Although Kim later said she forgave Rob for his no-show, during episodes of Keeping Up with the Kardashians, she has shown little sympathy for her less successful brother. During an argument on one episode, she accused family members of pandering to him.

"It's just like, at some point you just have to give it up," Kim said. "We all make his life so easy. 'Okay, we'll drive you around with a chauffeur so no one has to look at you.' It's pathetic."

Presley Gerber

The eldest son of supermodel, Cindy Crawford and her businessman husband, Rande Gerber, 21-year-old Presley has struggled to find the same levels of success as his 19-year-old supermodel sister, Kaia. The six-foot tall aspiring photographer was charged with a DUI in January last year, after he was pulled over by police and failed a sobriety test.

But it was when he took to Instagram in March to debut a face tattoo that read "Misunderstood" that it emerged the celebrity offspring had been in rehab for undisclosed reasons and had, according to Us Weekly, "[Been] hanging out with a group of people who've been negatively impacting him."

“Most and a lot of people can get a face lift, change genders, lip injections, etc and it’s offensive to say anything in today’s age, but I get a little face tattoo and now people love to hate me.. Hmmmm?” he wrote on his Instagram Story.

“If I thought this was going to ruin my face or I didn’t want this, I wouldn’t have done it. I think that’s a pretty obvious thing. [If you have anything] to say to me about this or anything else and my family or how I grew up or anything, I will give you my address, I promise, and you can come say it to my face,” he said. “It says 'misunderstood' because that’s how I’ve felt all my life.”

Presley has modelled for Dolce & Gabbana and Calvin Klein – and is signed to IMG Models, alongside the likes of Hailey Bieber, and Gigi and Bella Hadid.

However, while his sister has seen her career path paved by her well-connected mother, Presley admitted in 2018 that his has not been so clear.

"I had no idea that I was going to do [modelling]," he told The New York Times Style magazine. "I knew that I wanted to start a business and until the last year of high school I thought I was going to continue my education, but I started working as a model and introduced myself to a new world with which I have started again."

Presley, who recently added a gold tooth to his facial enhancements, has been teasing a new project on Instagram, writing, “Tell me this n that but I got my own plan”, but for now he’s been working in his father’s Malibu restaurant, Cafe Habana.

James Middleton

In January 2019, James Middleton, 33, wrote a poignant essay for the UK's Daily Mail about his struggle with depression, in which he addressed many of the issues which had plagued him throughout his life in the spotlight.

"During the day I'd drag myself up and go to work, then just stare with glazed eyes at my computer screen, willing the hours to tick by so I could drive home again," he wrote. "Debilitating inertia gripped me. I couldn't respond to the simplest message so I didn't open my emails. I couldn't communicate, even with those I loved best: my family and close friends."

Unlike his famous sisters, James has struggled to find his niche. With Kate marrying Prince William in 2011, followed by Pippa's wedding to James Matthews in 2017, his two sisters were considered to have "married well" – a societal norm that, while deemed acceptable for women, has often been frowned upon for men.

Company closures and ADD diagnosis

After calling time on his five-year relationship with British TV personality and socialite, Donna Air back in 2017, James struggled to make a success in business, shuttering two companies, The Cake Kit Company and Nice Cakes; while his personalised marshmallow company, Boomf, has recorded losses of £3 million (Dh14 million).

And the closures were something James later attributed to his diagnosis with Attention Deficit Disorder (ADD), which he also said is behind some of his strengths.

“ADD explains other things, too: why I’m restless, energetic and impulsive; why I start tasks but can’t complete them; why sometimes I seem impatient and don’t listen because my mind is galloping off on some flight of fancy,” says James. “However, I also see my ADD as a gift: it accounts for my creativity and emotional intensity. It means that I come up with fantastic, original ideas – but it also explains why I have had difficulties with the minutiae of running a business.”

Over the past year, James appears to have gotten back on a healthy track, becoming engaged to his French girlfriend, Alizee Thevenet in October last year, with the pair moving to rural Scotland for James to start a new role at the Glen Affric Lodge, owned by his brother-in-law James Matthews’ father.

“I know I’m richly blessed and live a privileged life. But it did not make me immune to depression,” he says “It is tricky to describe the condition. It is not merely sadness. It is an illness, a cancer of the mind.”