Prince William 'Chose Well' in Marrying Kate Middleton, Royal Insider Declares Decades After Special Encounter With Princess Diana

Jamie Lowther-Pinkerton carries the kind of credentials that give him genuine authority when it comes to the inner workings of the Palace.

His decades of service to the royal family — from his role attending to Queen Elizabeth, through decades in the armed forces, to his later position as private secretary to Princes William and Harry and then to Kate Middleton — make him uniquely positioned to offer insights.

His connection to the family reaches back even further than his official postings. During his early years in royal circles, Lowther-Pinkerton crossed paths with a different Princess of Wales, Princess Diana, whom he remembers fondly as "such a breath of fresh air."

Recalling those first encounters, he says: "This was in 1984, 1985. I sat next to her at lunch and she was great. She was a sort of really buzzy live wire. I loved all of the Queen Mother's very cool friends, but they were in their 80s. [Diana] was someone different."

After stepping down from his formal role in 2013, Lowther-Pinkerton remained close with the family, even returning from retirement to help with the young royals during King Charles' coronation in 2023. Today, he continues to maintain close ties to those he once served.

In a recent interview with The Times, Lowther-Pinkerton opened up about his admiration for Middleton. He was instrumental in planning Prince William and Middleton's 2011 wedding and provided crucial support as Middleton navigated her early years within the royal family. His regard for her is evident in his assessment: "She's a really cool woman. Amazing. He chose well. I think they'll be like my mum and dad. I think they're great."

He also characterized the Princess of Wales as "so sweet," recalling an official engagement where she greeted him warmly. The moment, though, left him flustered: "I nearly headbutted her. I didn't know if I should be bowing."

Prince William and Middleton's romance began in 2001 when they met as students at the University of St Andrews. After a brief split in 2007, the couple rekindled and went on to build a life together in the public eye.

He proposed in October 2010 during a private trip to Mount Kenya, presenting Middleton with the iconic sapphire and diamond ring that had once belonged to his mother, Princess Diana. Their wedding the following April at Westminster Abbey became a global event, watched by over two billion viewers worldwide.

Now the Prince and Princess of Wales, the couple share three children: Prince George, Princess Charlotte and Prince Louis.

Most recently, two important occasions occurred on a single day: Father's Day and Prince William's 44th birthday. The family shared a sweet message to Prince William: "Happy birthday and Father's Day to the best Papa in the World! We love you very much. C, G, C & L 💕."