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January 06, 2015 07:15 AM

Prince Andrew has faced tabloid headlines all his adult life – both laudatory and unsavory.

The Queen’s second son and fifth in line to the throne courted controversy with his one-time girlfriend actress Koo Stark, won admirers for his service with the Royal Navy in the Falklands War and endured endless media attention for his marriage to, split from and post-divorce friendship with the Duchess of York, Sarah Ferguson.

Now, he is engulfed in a scandal stemming from a friendship with a disgraced billionaire that mystified and troubled Buckingham Palace insiders.

The scandal broke last week after Florida court filings alleged Andrew had underage sex with a teen girl provided to him by billionaire Jeffrey Epstein on his private Caribbean Island, in London and New York. Buckingham Palace has issued repeated, emphatic denials of the allegations, made by a woman identified in the filings as Jane Doe 3. She is believed to be American Virginia Roberts.

PEOPLE has been unable to reach Roberts, but her father, Sky Roberts, told PEOPLE: “I support my daughter all the way. She has no reason to lie.” Roberts also said his daughter was writing a book.

Andrew, 54, met Florida billionaire Jeffrey Epstein, 61, in the 1990s, and the Andrew-Epstein friendship lasted well over a decade.

Epstein visited Windsor Castle in 2000 for Queen Elizabeth’s official birthday celebrations and went to the Royal Family’s country retreat at Sandringham the following winter. Andrew also entertained Epstein at the Scottish estate of Balmoral.

Despite Epstein’s jail term (he served 13 months of an 18-month sentence) after his 2008 conviction for soliciting sex with an underage girl following a plea bargain deal, Andrew remained in contact with him and was seen walking in New York with him after the businessman left jail. Andrew stepped down from his position as ambassador for U.K trade in the wake of the controversy.

‘Lived in an Ivory Tower’

A Palace source tells PEOPLE that Andrew has “acknowledged that the friendship was unwise, that it was unwise to meet Epstein.” Since their being seen together became public and the ensuing publicity that followed, the duke has not been in contact with him.

“The sad thing is that Andrew has always been a bit like this. He is terribly naïve and has a poor sense of judgment. But then he has lived in an ivory tower all his life. None of the older members of the royal family have very much experience of ordinary people apart from those who serve them,” says royal expert Ingrid Seward, author of Sarah, Duchess of York.

That he remained in contact with Epstein despite the conviction raised eyebrows – but clearly Andrew hadn’t realized the impact it would have. “His belief in being special and untouchable comes not just from being a prince, but from being his mother’s favorite,” says a royal observer.

Seward explains it differently. “He is incredibly loyal to his friends. That is his nature,” she says. “Look at Fergie – she is the prime example. Whatever they do he sticks with them.”

But, while he remakes his royal career boosting greater business skills in the worlds of science and technology, some say it is a shame that Andrew’s choice of friends ended what they saw as a thriving royal role helping promote British business abroad.

Robert Lacey, who has written books on royalty in both the U.K. and Saudi Arabia, says that Andrew had a lot to give Britain from his role on the world stage.

“He attracted crowds to meetings because of who he was. The royal family is a special British secret weapon that the Foreign Office can deploy to attract important business people who wouldn’t normally come out – and the prince knows his stuff. He remembers names very well and can seem very, very engaged. I have seen him operating at first hand and he’s a real professional. He has an impressive familiarity with technology and business practice,” says Lacey.

“But the problem with exploiting the magic of monarchy for commercial purposes is that the royals step down off the pedestal and risk becoming no more special or royal than anyone else.”

Prince Andrew and Virginia Roberts

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