The Duke of York’s royal life may have long been controversial, but the “Playboy Prince” also earned high regard for his bravery during the Falklands War.

However, the Queen’s second son will be best known as the Windsor who stepped down from royal duties amid the Epstein sex scandal after his reputation was left in tatters.

As a young man, he was one of the world’s most eligible bachelors and earned himself the nickname “Randy Andy” after being linked to a string of beautiful women.

But later in life his connections with controversial foreign figures raised concerns and he was dubbed “Air Miles Andy” after being criticised for his globe-trotting, especially helicopter trips to pursue his passion for golf.

At 22, Andrew saw active service in the Royal Navy as a Sea King helicopter pilot in the Falklands War. His service included flying his aircraft as a decoy target, trying to divert deadly Exocet missiles away from British ships.

He later married and divorced the bubbly, flame-haired Sarah “Fergie” Ferguson, who herself has generated some of the most humiliating royal scandals of modern times.

When a bachelor for a 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.

After serving for 22 years in the Royal Navy, the duke became the UK’s special representative for international trade and investment, but his 10 years in the role generated a great deal of controversy.

As a roving ambassador, one of his first tasks was a post-September 11 trip to New York, but he was criticised for attending a party during his stay.

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

His judgment was questioned after he held meetings with Libyan leader Colonel Muammar Gaddafi’s son Saif, and when he entertained the son-in-law of Tunisia’s ousted president Zine El Abidine Ben Ali at Buckingham Palace.

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

Tatiana Gfoeller, Washington’s ambassador to Kyrgyzstan, also said Andrew criticised the Serious Fraud Office investigation of an arms deal between British Aerospace and Saudi Arabia, and accused Guardian journalists of “poking their noses everywhere” for investigating the deal.

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”.

In 2011, it emerged that Andrew was friends with American financier Jeffrey Epstein, who was sentenced to 18 months in prison in 2008 for soliciting a minor for prostitution.

Photos surfaced of him with his arm around Virginia Giuffre, also known as Virginia Roberts, who claimed that Epstein employed her as a masseuse but exploited her while a teenage minor.

The duke was also pictured walking in New York’s Central Park with Epstein in December 2010, a year after Epstein’s release from prison, and this led him to quit his role as a trade envoy.

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 “unsavoury character”.

Tech-savvy Andrew, who was the first member of the royal family to have an official Twitter account under his own name, focused on his Pitch@Palace work, encouraging young entrepreneurs to embrace technology start-ups and launching a range of initiatives to inspire youth innovators.

Then in 2015, while enjoying a new year skiing holiday with his family, he was named in US court documents as having had sex with a 17-year-old three times between 1999 and 2002 in London, New York and on Epstein’s private Caribbean island when the girl was still a minor under US law.

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

She was identified in reports as Virginia Giuffre, the American teenager with whom Andrew had been pictured.

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.

The duke’s appearance on the BBC’s Newsnight programme was intended to draw a line under the matter.

But it was dubbed a “car crash”, with commentators questioning his responses and condemning his unsympathetic tone and lack of remorse over his friendship with the sex offender Epstein.

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.

The Epstein saga and the duke’s conduct during the on-camera interview ultimately led to his downfall – and the end of his official duties as a royal.