Inside Prince Andrew’s spectacular fall from grace from war hero to civil sex case

The Duke of York’s civil sex case will be settled outside of court, but there was a long fall from grace to this point for the ‘Playboy Prince’.

The settlement means that he will no longer face public trial and he might be spared some of the controversy around it.

Until the agreement, reached “in principle” today, Andrew would have faced a jury trial following accusations of sexual assault by Virginia Giuffre.

Andrew has come a long way from being a darling of the Royal family to embroiled in this scandal.

He was once held in regard for his bravery in the Falklands War where he served in the Royal Navy.

However, his reputation was left in tatters after links to Jeffrey Epstein and his sex scandal.

The Prince was once known as ‘Randy Andy’ after being linked to numerous women.

Prince Andrew, Virginia Giuffre and Ghislaine Maxwell


US District Court – Southern District)

However, he also earned the nickname ‘Air Miles Andy’ for his environmentally damaging globe-trotting antics and using helicopter trips to play golf.

At 22, Andrew served in the Falklands war as a Sea King helicopter pilot.

His service included flying his aircraft as a decoy target, trying to divert deadly Exocet missiles away from British ships.

Later on, he married and then divorced Sarah ‘Fergie’ Ferguson, who herself was involved in a number of scandals including the ‘fake sheikh’.

When he was single for the second time, Andrew again made headlines, having been spotted cavorting with topless women on holiday in Thailand, and attending a “hookers and pimps” party with Robert Maxwell’s daughter, Ghislaine Maxwell, in the US.

The Queen stripped the duke of his military titles and royal patronages



After 22 years of service in the Royal Navy, the duke went on to become the UK’s special representative for international trade and investment.

But across his decade in the role he continued to generate controversy.

One of his first tasks was a post 9/11 trip to New York, but he was criticized for attending a party during his stay as America mourned one of the deadliest events in its history.

Andrew has also faced questions about his connections to politicians in Azerbaijan, Kazakhstan, Tunisia, Libya and Turkmenistan.

Jeffrey Epstein was charged with procuring a minor for prostitution



He held meetings with Libyan leader Colonel Gaddafi’s son Saif, and even entertained the son-in-law of Tunisia’s ousted president Zine El Abidine Ben Ali at Buckingham Palace.

His relations with Timur Kulibayev, son-in-law of the then-president of Kazakhstan, were also scrutinized after Mr Kulibayev purchased the duke’s Sunninghill Park home for £3 million more than its £12 million asking price in 2007.

Simon Wilson, Britain’s deputy head of mission in Bahrain from 2001 to 2005, wrote in the Daily Mail that the duke was “more commonly known among the British diplomatic community in the Gulf as HBH: His Buffoon Highness”.

However, in 2010, pictures emerged of the duke waking in New York’s Central Park with Epstein, leading to the prince quitting the role as trade envoy.

A year later Andrew’s friendship with Epstein emerged after the American financier was sentenced to 18 months in prison in 2008 for soliciting a minor for prostitution.

Infamous photos surfaced of him with his arm around Virginia Giuffre who claimed that Epstein employed her as a masseuse but exploited her as a teenager.

In 2013, Andrew was elected a Fellow of the Royal Society, but Britain’s pre-eminent scientific institution faced unprecedented dissent from members over the move, with one professor describing the duke as an “unsavory character”.

Then, whilst enjoying a New Year skiing holiday with his family two years later, he was named in US court documents as having had sex with Giuffre a number of times.

Andrew and Fergie at the announcement of their engagement in 1986


Tim Graham Photo Library via Getty Images)

She alleged she was “procured” for the duke by Epstein, whom she accused of using her as a “sex slave”.

The duke vehemently denied the allegation.

In April 2015, a US federal judge ordered the claims to be struck from civil court records as the long-running lawsuit against Epstein continued.

But Andrew’s association with Epstein hit the headlines once again in 2019, amid ongoing investigations into the American, who killed himself in prison in August that year while awaiting trial on sex trafficking and conspiracy charges.

At this point the duke’s reputation was tied deeply to the claims linking him to Epstein and the sex abuse case.

Melania Trump, Prince Andrew, Gwendolyn Beck and Jeffrey Epstein at a party at the Mar-a-Lago club, Palm Beach, Florida, February 12, 2000



The duke’s appearance on the BBC’s Newsnight program later in November was intended to draw a line under the matter.

However, it was nearly universally judged as a ‘car crash’ interview thanks to his unsympathetic tone, lack of remorse, and claims like he couldn’t sweat at one point in his life.

During the interview, Andrew denied that he slept with Ms Giuffre, saying one encounter in 2001 did not happen as he had spent the day with his daughter, Princess Beatrice, taking her to Pizza Express in Woking for a party.

The same alleged sexual liaison, which the American said began with the royal sweating heavily as they danced at London nightclub Tramp, was later branded factually wrong as the duke said he had a medical condition at the time which meant he did not sweat.

And he twice stated that his relationship with sex offender Epstein had provided “seriously beneficial outcomes”, giving him the opportunity to meet people and prepare for his future role as a trade envoy.

In January, Andrew’s lawyers attempted to throw out the civil sex case brought by Ms Giuffre, but a judge rejected this and ruled the case could go to trial.

The Queen stripped Andrew of his honorary military roles in response, and he gave up his HRH style, before demanding a jury trial.

But on February 15, their lawyers reached an out-of-court settlement in what appears to be a conclusion to the case.

Court documents show the duke will make a “substantial donation to Ms Giuffre’s charity in support of victims’ rights”.

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George Holan

George Holan is chief editor at Plainsmen Post and has articles published in many notable publications in the last decade.

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