In 2010, Prince William and Catherine, Princess of Wales got engaged. However, Michael has faced challenges and sadness, especially when it came to his daughter’s wedding. It can be nerve-wracking to walk your child down the aisle, and even more so when you have to do it in front of an estimated billion people and adhere to the royal family’s traditional wedding rules. Michael is quiet and reserved and prefers to avoid the spotlight when possible. In a December 2018 interview with The Telegraph, Carole described her husband as “rather shy,” something he had to overcome for his new public persona.
Still, at least he can relax behind closed doors, something his son-in-law has always appreciated. According to royal expert Christopher Andersen, William’s relationship with Kate’s parents is strong. “In many ways, he is closer to Michael and Carole Middleton than he ever was with his own father,” he told Fox News Digital in April 2024. But the former businessman’s entry into the nobility has still been taxing. Here are some of the sad details of Michael’s journey.
Michael’s shattered dreams of becoming a pilot
Michael Middleton came from a background of wealth and privilege. He attended the private school Clifton College, and by all accounts, Michael was a high achiever both in the classroom and on the sports field. “He did very well, becoming a prefect himself and, looking at his record, represented the school at rugby in the 1st XV and getting his tennis colors,” a former pupil, Stephen Bell, told The Newark Advertiser in April 2011, sharing that the school was “a miserable existence, but it got better as you got older.”
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Micheal followed in his father’s footsteps by attending Clifton, and he was keen to continue after graduation. His dad, Peter Francis Middleton, was a captain in the Royal Air Force and later became a commercial pilot. Michael also had a passion for the skies, but sadly, he could not fulfill his dream of earning his wings because his eyesight wasn’t good enough. Instead, he trained to be a dispatcher.
Michael was also forced to change path later in life when he and his wife, Carole Middleton, were persuaded to retire early due to their daughter’s royal role. “Anything the Middletons do will inevitably swing back on Kate, so it’s best that her mum and dad keep a low profile moving forward,” a source told The Express in November 2023.
Michael’s family press assault
Michael Middleton has more in the bank than your regular Joe Schmo, but some in high society still looked down upon his family. The press branded his family “the Middle-Class Middletons” and mocked them. They were accused of being social climbers, and Michael’s wife, Carole Middleton, was particularly singled out. The Daily Mail dubbed her “doors to manual” because of her career as an air steward, and its coverage was passive-aggressive in the way that Brits excel at. “At Ascot, Carole felt sufficiently at ease to bray with laughter at one of Philip’s jokes as they watched racegoers from the royal box — even if such a raucous laugh was the sort of thing that would have raised eyebrows at Downton Abbey,” The Mail wrote in July 2012.
Michael’s daughters didn’t escape ridicule either. Catherine, Princess of Wales, and her sister, Pippa Middleton, were nicknamed “the wisteria sisters” because they were “highly decorative, terribly fragrant, and have a ferocious ability to climb.”
Given how close Michael is to his family, it had to sting. Still, he always kept a stiff upper lip. His steadfastness and self-assurance are credited with Kate remaining down to earth despite her heady rise to royalty. “Kate’s feet are still on the ground, largely because of Michael,” a friend told Vanity Fair in April 2011. “He doesn’t get too swept up in the grandeur of her new life, and Kate loves him for that. She gets a lot of her characteristics from him.”
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Michael’s business debts Karwai Tang/Getty Images
Unfortunately, Michael Middleton unintentionally gave the British press plenty of ammunition to attack him when his business collapsed in June 2023. Michael launched Party Pieces in 1987 with his wife, Carole Middleton. Initially, the company organized kids’ parties but later segued into selling party supplies, decorations, and gifts. It was a successful and lucrative venture until COVID-19 hit, and revenue dried up. The company could not pay the $3.41 million owed to creditors and was forced into administration — an alternative option to bankruptcy available in Britain.
“For nearly two years, nobody was giving children’s parties, and the lingering effects have been devastating. The entire market for what Party Pieces was selling went straight off the end of a cliff,” royal expert Chris Andersen told US Weekly in April 2024.
According to The Times, unfortunately, Party Pieces’ assets were insufficient to recoup all of the insolvency costs, leaving an outstanding debt of [$341,500], which Michael and Carole are reportedly unable to pay. However, never fear! Anderson insisted the Middletons are not going to end up on the street. “People shouldn’t make the mistake that the Middletons are broke because they decidedly are not,” he said. “Their business went belly-up because of things entirely out of their control, but that doesn’t mean they haven’t got substantial personal assets.”
Michael’s worries about his son James
Michael Middleton has always been there for all three of his children, especially during tough times. This was something his son, James Middleton, needed during a year-long debilitating bout of clinical depression that started at the end of 2016. He wrote about his battle and his gratitude for his family’s support in a January 2019 piece for The Daily Mail.
“I know I’m richly blessed and live a privileged life. But it did not make me immune to depression. It is tricky to describe the condition. It is not merely sadness. It is an illness, a cancer of the mind,” James shared. He said he battled his dark thoughts for a year until the loneliness and feelings of desperation became too much for him to deal with alone.
James sought treatment from a psychiatrist and finally opened up to his family, whom he’d stopped communicating with, leaving them “desperately worried about me for months.” He said they were supportive, in addition to learning all that they could about depression and the ways to help him. James said the experience taught him that there is no shame in reaching out and talking publicly about mental health issues. “If I could leave you with just one thought, it would be this: ‘It’s OK not to be OK.’ That is the mantra that gave me the strength to speak out,” he wrote.
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If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.
Michael’s heartbreak over Kate’s cancer diagnosis
Michael Middleton was understandably devastated to learn of his daughter, Catherine, Princess of Wales’ cancer diagnosis. Kate went public with the news in March 2024, following mounting speculation over her absence from the spotlight. “It has been an incredibly tough couple of months for our entire family. But I’ve had a fantastic medical team who have taken great care of me, for which I am so grateful,” she said. “…This, of course, came as a huge shock, and William and I have been doing everything we can to process and manage this privately for the sake of our young family.”
As Kate underwent chemotherapy and began her recovery, her parents stepped up. They rallied around their daughter and her husband, William Prince of Wales, and supported them in their time of need. “Carole and Michael will have essentially thrown a safety blanket around the young children to help protect them. In times like this for Kate, it is hugely important. It is crucial the children are looked after carefully,” Royal commentator and biographer Duncan Larcombe told The Mirror in March 2024.
Meanwhile, royal expert Katie Nicholl told Entertainment Tonight that the Middletons are Kate’s “real anchors in life” and integral to her recovery. “While you certainly don’t see them photographed together very often, they are very much there in the background. They are absolutely fundamental,” she said.