Inside the world of Prince Andrew

Once a Falklands war hero, the Duke of York’s associations with Jeffrey Epstein may have damaged his reputation beyond repair

Prince Andrew
(Image credit: Max Mumby/Indigo/Getty Images)

Once seen as Britain’s “playboy” prince and frequently touted as the Queen’s favourite son, Prince Andrew’s association with the late paedophile Jeffrey Epstein has destroyed his standing in the eyes of the British public and tarnished the reputation of the Royal Family across the globe.

The playboy prince

In his youth he was considered “one of the world’s most eligible bachelors”, earning himself the tabloid nickname “Randy Andy” after being linked to a “string of beautiful women”, said the London Evening Standard. This included American actress Koo Stark, a relationship which came to an “abrupt end” in 1980 when it was revealed she had starred in a “racy” movie ten years earlier, said the Daily Mail.

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But in his later years, Prince Andrew’s reputation in the British press as a Lothario royal would sour as he was linked to controversial foreign figures and criticised for his globe-trotting habits – in particular, helicopter trips to play golf – which would earn him the moniker “Air Miles Andy”, a nickname that stuck for decades.

At the time of his birth, 19 February 1960, Andrew was the “first child born to a reigning British monarch (male or female) since 1857”, according to Britannica, as heir to the throne Prince Charles was born when the Queen was still Princess Elizabeth. For the first 22 years of his life he was second in line to the throne, behind Charles, and ahead of his older sister Princess Anne, until the birth of his nephew Prince William in 1982.

The birth of subsequent generations means he is now only ninth in the order of succession, following the latest arrivals: Prince Harry and Meghan Markle’s children, Archie and Lilibet.

Active duty during the Falklands War

After being educated at Gordonstoun School in Scotland, as his father Prince Philip and his brother Charles had been, Andrew entered Britannia Royal Naval College in Dartmouth, Devon, in 1979 to train as a naval officer and then underwent pilot training in fixed-wing aircraft and helicopters.

At 22 he saw active service in the Royal Navy as a Sea King helicopter pilot on the aircraft carrier HMS Invincible. It was a role that “put him in the front line during the early stages of the conflict” when the Argentinian air force began a campaign targeting Royal Navy warships carrying Sear Harrier jump-jets and Sea Kings, said The Times.

“There is little doubt that his life was in constant danger throughout the ten-week campaign,” said the newspaper, with one of his regular roles to act as a decoy to draw away incoming Exocet missiles from HMS Invincible by confusing their guidance system.

On his return he was “greeted by the Queen as his ship pulled into the harbour”, said The Mirror. “He came back a hero and was very much the golden boy of the royal family,” royal expert Katie Nicholl told the newspaper.

Marriage to Sarah Ferguson

On 23 July 1986 Prince Andrew married Sarah Ferguson, popularly known as “Fergie”, in a grand ceremony at Westminster Abbey. They received the title of Duke and Duchess of York on the same day.

But the relationship is “believed to have begun unravelling soon after they were married”, as Prince Andrew’s naval career meant he was away for long periods, and “as a result, the couple reportedly only saw each other for around 40 days per year”, said The Independent.

The couple separated in March 1992 and divorced in May 1996. Soon after the separation Ferguson became embroiled in a scandal that would estrange her from the Royal Family for several years. Photographs of her and John Bryan, an American business manager, were published in the Daily Mirror which showed Bryan “kissing the duchess’s toes as she sunbathed topless”.

But the pair have always remained close, with friends of the one-time couple believing remarriage could “be on the cards”, said Vanity Fair. Talks of remarriage have reportedly “reignited” since the death of the Duke of Edinburgh, as this was considered impossible while the Duke was alive due to a reported “long-term rift” between him and his former daughter-in-law.

Friendship with Jeffrey Epstein

The prince’s friendships have long been a point of controversy, with his questionable associations ranging from “lunching at Buckingham Palace with a ‘notorious’ member of the former Tunisian regime, to taking a holiday with a Libyan gun smuggler”, said the BBC in 2011.

But it has been Andrew’s friendship with Epstein that has proved the most damaging to his reputation, and that of the Royal Family.

There was “huge controversy” after he was photographed meeting the disgraced financier in New York’s Central Park in December 2010, after the tycoon had served an 18-month prison sentence for soliciting a minor for prostitution, said the broadcaster.

And in 2015, in US court documents, he was accused of having sex with Virginia Giuffre at three of Epstein’s properties when she was 17 years old and a minor under US law. Prince Andrew has always denied the allegations.

His associations with Epstein hit the headlines once again in 2019 when the disgraced tycoon killed himself in prison while awaiting trial on sex trafficking and conspiracy charges.

A Newsnight interview with Emily Maitlis was intended to draw a line under Prince Andrew’s associations with Epstein and the allegations brought against him by Giuffre.

During the interview, the duke denied he slept with Giuffre, saying an encounter alleged to have taken place in 2001 could not have taken place because he was at a Pizza Express in Woking, Surrey, with his daughter Princess Beatrice.

He also said Giuffre’s claim that he was sweaty at a nightclub could not be true because an “overdose of adrenaline in the Falklands war” had left him unable to sweat.

The interview ultimately led to Prince Andrew stepping back from Royal duties and public life.

Two years on, a New York judge is deciding whether to allow Giuffre to pursue her civil case. Judge Lewis Kaplan has said he will deliver his decision “pretty soon”, leaving Andrew’s hopes of having the case thrown out of court hanging in the balance, said the i news site.

Should Kaplan dismiss the case, Andrew “will have won and will begin the long path to rebuilding his reputation”, added the website.

But if he allows the case to go forward, Andrew “could face damaging testimony”, said The New York Times, and that “would plunge the House of Windsor back into scandal at the very moment it hopes to use the Platinum Jubilee to remind Britons of the queen’s extraordinary longevity and largely blemish-free record of service”.

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 Sorcha Bradley is a writer at The Week and a regular on “The Week Unwrapped” podcast. She worked at The Week magazine for a year and a half before taking up her current role with the digital team, where she mostly covers UK current affairs and politics. Before joining The Week, Sorcha worked at slow-news start-up Tortoise Media. She has also written for Sky News, The Sunday Times, the London Evening Standard and Grazia magazine, among other publications. She has a master’s in newspaper journalism from City, University of London, where she specialised in political journalism.