American viewers may not be familiar with James Hewitt’s name in the latest season of The Crown but the military man is at the heart of one of the biggest affairs to besiege the monarchy in the late 20th century.

Born into a military family in 1958, Hewitt’s father was an officer in the British Navy and he himself attended Millfield School as a young man. At the age of 20, Hewitt followed his family’s tradition of service by joining the Brigade of Guards, a unit of the British Army.

Hewitt commanded 14 Challenger tanks as part of Operation Desert Storm during the Gulf War. In 1986, the moment that would ultimately launch him into the public consciousness was when he met Princess Diana at a party organised by her lady-in-waiting, Hazel West.

“Their first conversation felt natural, she said, and it was this that sparked her attraction. As she put it, they got along famously,” Princess Diana’s royal protection officer, Ken Wharfe, wrote in his book Diana: Closely Guarded Secret. “He told her he was a riding instructor and, when she confessed she was afraid of horses, offered to help her overcome her fear.”

Hewitt became Princess Diana’s riding instructor and not long after that, they were romantically involved in an arrangement that would last for several years. Diana’s marriage to Prince Charles was known to be rocky at the time she met Hewitt and Charles was reportedly already carrying on his own liaison with his former girlfriend (and future wife) Camilla Parker-Bowles, which Diana’s bodyguard, Wharfe posited may have contributed to her willingness to start an affair with Hewitt.

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“Hewitt, a natural womaniser, gave her the attention and affection she relished, and then the passion she yearned for,” he wrote. “The pair usually met at an old cottage in Devon belonging to Shirley, Hewitt’s mother, where the creaking bedroom floorboards told the story more loudly than any confession.”

Hewitt painted the romance as a bit more understated. “I’d cook and [Diana] would wash up,” he said on the Australian television programme, Sunday Night in 2017.”Just dinner and relaxing and laughing.” Despite how the relationship went on, by the end of the 1980s, Hewitt was given command of a tank squadron which led him abroad.

“Diana felt betrayed: he had chosen his career over her. At first, she did everything she could to prevent him from going, even threatening to speak to his commanding officer,” Wharfe writes. “When James refused to give up his career, Diana let the affair wane.” Though Diana stayed in contact with Hewitt after he was stationed in Saudi Arabia in 1990, the relationship was, apparently, over.

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Princess Diana had a brief affair with James Hewitt.Picture: Instagram

In 1994, Hewitt catapulted into the international spotlight when, shortly after retiring from the armed forces, he partnered with author Anna Pasternak for the book Princess in Love. The book was about the extramarital affair between Hewitt and Diana over the course of five years between 1986 and 1991. Even though Diana and Prince Charles formally separated in 1992, the news created a scandal and the book quickly became a best-seller.

In an interview with BBC’s Panorama in 1995, less than a year before Charles and Diana’s official divorce, Diana confirmed the affair. “Yes, I adored him. Yes, I was in love with him. But I was very let down,” she said of Hewitt’s involvement in the publication of the book. Since the death of Diana in 1997, Hewitt continued to make news intermittently for continued revelations about the affair. In 1999, he released the book Love and War further detailing the affair and has given numerous interviews on the subject in the ensuing decades.

Hewitt has attempted several times, or has been accused of attempting to sell more than 60 love letters written to him by Diana while he was serving in the Gulf War, most notably, in a News of the World sting two years after the Princess’s death which revealed that Hewitt had suggested a price of £10 million for the mementos. The letters have never been made public and in a 2009 interview with the Telegraph, he stated that he intended to keep them forever.

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The former military man opened a golf driving range in the mid’90s after his retirement from the military. Hewitt later made several appearances on reality TV including a stint on X-Factor and a 2004 win on the Big Brother-esque competition Back to Reality. Hewitt moved to Marbella, Spain to open The Polo House bar in 2009 and it later closed in 2013. He was hospitalised for a heart attack in 2017 but was subsequently released.

Since his affair with Diana, fans have often speculated that Hewitt could be the father of Prince Harry, citing a resemblance between the two, especially their red hair.

Hewitt has uniformly denied these claims. Likewise, Wharfe wrote, “A simple comparison of dates proves it is impossible for Hewitt to be Harry’s father. … Harry was born on September 15, 1984, which means he was conceived around Christmas 1983, when his brother, William, was 18 months old. Diana did not meet James Hewitt until the summer of 1986.”