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Prince of scandal: Duke of York's hefty list of bloopers

As Buckingham Palace denies the latest allegations against Prince Andrew, Emily Hourican looks back at the Duke of York's hefty list of bloopers

How Buckingham Palace must look back with fond regret to the innocent days of the early 1990s, when Prince Andrew was the subject of affectionately raucous headlines after a photograph of him skinny-dipping appeared in The Sun.

That seems like another world now the prince has been named in allegations by a young American woman, a mother of three, who is taking a civil case filed in Florida against American billionaire Jeffrey Epstein, claiming that she was his 'sex slave' for years, during which time, and while still only 17 and therefore underage in the state's law, she alleges she had sex with Prince Andrew three times.

The woman, known formally as 'Jane Doe #3', but widely named as Virginia Roberts, claims she had sex with the prince in London, New York, and on Epstein's private island in the Caribbean, during "an orgy with numerous other underage girls", and that she was told by Epstein to "give the prince whatever he demanded".

For the second time in recent days, the Prince's former wife Sarah, Duchess of York, has leapt to her ex-husband's defence, telling the NBC Today programme in the USA that he is "a humongously good man", adding: "I won't stand by and have his character defamed. My integrity and the American people know my integrity and my integrity is of a great man and I will not have one word said about him on any level. Any level."

And, of course, the Palace has also strongly denied these allegations - twice in fact, which is something, given that even one official denial of media stories by Royalty is unusual - in a statement saying "any suggestion of impropriety with underage minors is categorically untrue". However, so far, aides have not explained the extent of Andrew's association with the man at the centre of the allegations.

Jeffrey Epstein is a convicted sex offender who did jail time in America in 2008 for soliciting prostitution among under-age girls. The 13 months he served were part of a prosecution deal which saw him plead guilty to soliciting paid sex with a minor, and a federal inquiry dropped. He is already known to be a friend of Prince Andrew - who has often shown a lack of judgment in choosing his acquaintances - and indeed earlier photographs of the prince with his arm around the waist of Virginia Roberts, then just 17, during one of Epstein's trips to London, surfaced nearly three years ago. In the photograph, Virginia is fresh-faced, smiley and wholesome-looking. The prince himself looks relaxed.

Although the prince was quick to insist at the time that there was nothing to the photo, and that he had met Virginia only momentarily, the association with Epstein was sufficiently embarrassing that he promptly resigned as Special Trade Representative, and has struggled to define an official role for himself since, although he is still said by the Palace to be devoted to furthering Britain's business interests. Indeed, Boris Johnson came out in support of Andrew the week before last, saying "Prince Andrew, let us be very clear, is a guy who does a huge amount of unsung, unheralded work for this country. People go on and on about air miles and so on. But I've seen that guy get out there and sell this country, try and help British firms get business around the world."

Back in 2011, the scandal was short-lived - just another chapter in the rather hefty book of Andrew's bloopers - but the Epstein case, which has a variety of tentacles, has dragged on for several years, and most likely will continue to stall, stumble and grow various heads as those named by Roberts defend their reputations.

Actually, it was Andrew's ex-wife, Sarah Ferguson, who seemed to take most of the heat in 2011. Andrew, whose loyalty to the equally-controversy-prone Fergie has cost him dear before, had apparently confided in Epstein details of her on-going debt problems - she then owed some £5m - and Epstein, either through the kind of bluff posturing that makes £58,000 small change to a billionaire, or in order to consolidate what might be a useful friendship - offered to step in with a loan of £58,000, of which £15,000 was delivered. Fergie, therefore, was prime mover in the initial Epstein scandal.

"I ... know that this was a gigantic error of judgment on my behalf," she admitted at the time, sobbing out her contrition to the media. "Once again my errors have compounded and rebounded and also inadvertently impacted on the man I admire most in the world, the duke. He has supported me and come to my rescue again and again and there is absolutely nothing that I would not do for him ... I would throw myself under a bus for him," said Fergie, who - fine words aside - seemed incapable of simply sparing him everyday embarrassment; then adding that she was "a fiery Irish redhead and I am to remain strong, fight strong and try to do what is right.

"The duke is a man who does not know how to tell an untruth or behave dishonourably. There have been errors of judgment but nothing substantive has been done wrong by him, ever," she insisted, concluding, "the duke and I are a united front on all that has happened over the last few days. He, my girls and I are a unit who will always stick together even though we live separate lives."

Fergie is still sticking by her man, even though Virginia Roberts now alleges that she had sex with the Prince the very night the photograph of her with the prince was taken. "The York family is a tight unit," Fergie reiterated from the ski slopes of Verbier just over a week ago. "We've always been a tight unit ... He is the greatest man there is. It was the finest moment of my life in 1986 when I married him. He is a great man, the best man in the world.'

The sensational allegations were made in a Florida court the week before last, as part of a civil case taken by Virginia Roberts against Epstein. In this, she alleges that she was his "sex slave" for years, and was part of a "string of under-age girls". She is not the only woman to allege this. Two other 'Jane Does' have given testimony in the long-running case, and some of Epstein's alleged victims have already reached out-of-court settlements.

Roberts claims that she was just 15 and working as a changing room assistant at Donald Trump's country club in Palm Beach, Florida when she was introduced by Ghislaine Maxwell to Epstein at his mansion, where she apparently gave him an 'erotic massage', and was paid £130. From there, Epstein apparently "converted her into what is commonly referred to as a 'sex slave'", introducing her into an alleged international sex trafficking ring involving under-age girls, set up to serve the rich and famous. Maxwell denies the allegations.

Virginia Roberts, meanwhile, responded to the storm of furious denials set off by her claims, by stating through her lawyers "These types of aggressive attacks on me are exactly the reason why sexual abuse victims typically remain silent and the reason why I did for a long time."

Whatever transpires next, the linking of Prince Andrew with such a dark story can only cause deep embarrassment to the royal family. Back when he was appointed Special Trade Representative to the British government, some 13 years ago, an unnamed Labour MP was quoted as saying: "I couldn't believe it. It shows an appalling lack of judgment. I suppose there are some countries where his presence might impress, but he's a liability."

And indeed, Andrew's 10 years in the role were dogged by repeated controversies. There was the jovial nickname - 'Airmiles Andy' - given in honour of his fondness for hopping into a helicopter for the kind of journey a car could easily have performed. The meetings with Colonel Gaddafi's son, Saif al-Islam. There was the holiday in Tunisia, paid for by Tarek Kaituni, a convicted Libyan gun smuggler, before the Prince went on to visit Col Gaddafi. The business lunch hosted at Buckingham Palace for Sakher el-Materi, son-in-law of the now-deposed Tunisian president Zine al-Abidine Ben Ali, who was later investigated for money laundering. And of course the sale of Sunninghill Park, the house bought for him by the Queen when Andrew married Fergie.

Andrew later sold the house privately, in a deal brokered by socialite Goga Ashkenazi, to Kazakh billionaire Timur Kulibayev, who paid £15m - a full £3m over the asking price, although the house had been on the market for several years by then and there were no other offers - and never lived there.

With it all, and despite the fact that Andrew is teetotal and always seemed faintly out of his depth at the kind of Eurotrash parties he enjoyed, went a faint 'Playboy Prince' image. Probably the Aston Martin he drove was responsible, as well as the photos that appeared of him on board various yachts, in various jet-setty corners of the world, surrounded by bikini-clad girls, and once, off the coast of Thailand, even a gang of topless girls, including Jenny Frost from Atomic Kitten.

The night with Courtney Love added a dash of almost-rock-n-roll glamour too - he once paid a late-night visit to her house in Hollywood, "Prince Andrew turns up at my house at one in the morning and he wants to party," she said while promoting her diaries, Dirty Blonde, on Russell Brand's chat show in 2006. "He's come to Hollywood to look for chicks. I don't know what he expected at my house; I think he thought it was going to be like a party." He was out of luck, if indeed those were his intentions, and he and Love ended up having a quiet cup of tea together.

Andrew's extravagance, said to rival even the late Princess Margaret's, has long been badly viewed. In fact, he is a living cautionary tale to Prince Harry - an example of some of the many things that can go wrong for junior royals without any formal role.

Despite sporadic speculation over Andrew's sexuality - Fergie herself once declared, "There is absolutely no chance he can be gay. A lot of people believe that's true. And it is categorically not true," in a US TV interview with Diane Sawyer - the problem with Andrew has always been women: too many of them, the wrong ones, the right ones at the wrong time. In the years since his divorce from Fergie, he has been linked to Denise Martell, a former Playboy model, PR girls Aurelia Cecil and Caroline Stanbury, businesswoman Amanda Staveley, and actress Angie Everhart.

However, no second marriage ever came about, and Andrew's most enduring relationship is still with his ex-wife. Together they are devoted to bringing up their daughters as well as possible. The couple still share a house - the Royal Lodge.

Who knows how much any of this could have been avoided had Andrew made a happier marriage? His loyalty to Fergie - and hers to him - is undoubted, but together they seem an explosive and not entirely successful combination, landing in hot water both together and separately. Certainly, the scandal that erupted when Andrew was forbidden to marry his first love, American actress Koo Stark, because she had appeared in a naked lesbian shower scene in a film called Emily, must seem charmingly slight after all these years.

For a man who was surely raised to understand the necessity for being above reproach, the prince seems not to grasp that discretion is still the better part of valour.

According to royal historian Robert Lacey, when the Queen was planning a 'second round' of children, after Charles and Anne, Prince Philip suggested that, "the last thing the world needs is more royal mouths to feed". This might look like unexpected prescience from the royal consort, or simply a shrewd understanding that a massive allowance, limited responsibility, insufficient duties and an ingrained sense of entitlement are a potentially explosive combination.

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