In the days when a stricter etiquette applied to the public behaviour of members of the royal family, British princesses were reputedly taught to keep their chins up when walking downstairs. Unfortunately, there doesn’t seem to have been any rule requiring British princes to stay away from convicted paedophiles.

The sorry saga of Prince Andrew’s involvement with Jeffrey Epstein, the New York multimillionaire accused of devoting much of his adult life to sexually abusing children, has presented the monarchy with a challenge that no arbiter of etiquette can ever have envisaged.

How did a son of the Queen of England turn up as a prime witness to one of the ugliest cases of organised slime ever brought before an American court? And what on earth have Andrew’s chubby fingers got to do with it?

Epstein’s suicide in a New York jail cell last month may have forced a premature end to the proceedings against the tycoon, but there is every sign this sad and profoundly disturbing case will continue to haunt Andrew for years to come.

A prime witness to one of the ugliest cases of organised slime ever brought before an American court.

The Duke of York is understood to have provided his mother with a personal assurance that he did not participate in Epstein’s warped activities. Buckingham Palace has repeatedly insisted that “any suggestion of impropriety with underage minors is categorically untrue”.

A chubby lot of good that has done so far in a case that lurches daily between the monstrous and the risible.

Anonymous sources put it about last week that the now notorious photograph of Andrew with his arm around the waist of Virginia Roberts Giuffre, one of Epstein’s principal accusers, may have been doctored. The proof? The fingers clasped around the then 17-year-old’s waist are apparently not as plump as the prince’s.

Strangely, these objections were not lodged when the photo was first published in 2015. It has been in the possession of the FBI since 2011 and no US official has questioned its authenticity.

One thing is now abundantly clear in what seems to have become a desperate rearguard mission to protect what’s left of Andrew’s reputation: that mission started far too late.

Whatever one makes of the lurid allegations of massages, orgies and birthday parties with 12-year-old girls, the Epstein scandal has from the start been a public relations disaster for the royal family. No one at Buckingham Palace appears to have realised that the #MeToo movement might reignite the seemingly dormant Epstein case, in which the prince has figured for almost two decades.

If any effort was made to “get in front of the story” — the crucial first move for most PR professionals — it failed pitifully.

Crisis Mismanagement

Far from striking pre-emptively to protect Andrew in advance of the coming crisis, the palace has been dragged, whimpering ineffectually, behind every twist and turn of the case, whether it was the private jet logs apparently placing the prince on board Epstein’s “Lolita express”; or a photograph of him standing inside Epstein’s home, waving a young woman goodbye; or the salacious allegations that a Russian woman was spotted giving him a foot massage.

Andrew’s response — that he was “appalled” by recent reports of Epstein’s behaviour and “deplores the exploitation of any human being” — failed to explain why he wasn’t more appalled in 2010, when he visited his friend after the latter’s release from jail.

Epstein served 13 months on a charge of procuring an underage girl for prostitution; his exploitation of young women was scarcely a secret. “It’s a fiasco,” a royal source admitted last week.

Prince Andrew brandishes a paint gun while visiting the Watts neighborhood of Los Angeles in 1984.

Yet this is not just a story of courtiers out of touch with modern mores, unable to cope with the blistering pace of a multinational social media swarm. At the heart of the Epstein hatefest stands a prickly, difficult and frequently reckless English prince who has never learnt how to make himself liked by the British public.

“The Duke of York has never been one to take advice that doesn’t suit him and he doesn’t hold back in letting you know what to do with advice that he doesn’t want to hear,” a former royal aide told The Sunday Times last week. Another royal source added: “Nobody will have sat him down and told him he should lie low, because he tends not to listen.”

As the second son of a British monarch, Andrew faced the inevitable challenge of finding a meaningful role as “spare” to the heir, an insurance policy in case of mishap.

“The Duke of York has never been one to take advice that doesn’t suit him.”

The medical uncertainties of centuries past lent second sons more heft: Henry VIII, Charles I and George V were notable “spares” who ascended to the throne when their older brothers died prematurely. Others embarked on military conquests, providing a template that endured. Andrew joined the Royal Navy from school and went on to enjoy what, in retrospect, were some of his very few moments of popular appeal.

After training as a helicopter pilot, he served in the Falklands on HMS Invincible, a mission he could easily have dodged — and which reports at the time suggested his mother would have preferred him to decline.

Yet the lustre he derived from his military exploits was soon diluted by foolish displays of public boorishness and an apparent determination to live up to his nickname of “Randy Andy”.

Randy Andy’s Brazen Hussy

On a 1984 visit to Los Angeles he aimed a paint gun at a group of press photographers, damaging equipment and ensuring that his laudable visit to a housing project would be overshadowed by reports of juvenile tomfoolery (his aides at the time claimed he had fired the paint gun accidentally).

A couple of years later it emerged that while serving as a pilot on HMS Brazen he had nicknamed his helicopter “Hussy”. Flying a brazen hussy was doubtless a jolly jape in the mid-1980s, but there were signs even then that Andrew was having trouble growing up.

Prince Andrew as a Royal Navy helicopter pilot of the H.M.S. Brazen in 1984.

In his 1983 book Andrew: The Playboy Prince, the royal biographer Andrew Morton describes a visit to Pensacola, Florida, where the prince’s ship had docked. His first trip ashore was to a club full of “topless go-go girls”, one of whom declared afterwards: “Now I know where he gets his Randy Andy nickname.” The dancer later renamed her act the “Randy Andy Eye Popper”.

Suffice it to say that Andrew’s ability to attract negative headlines has remained undiminished over the decades. If anyone had hoped that marriage might settle him down, his subsequent choice of wife merely amplified the uproar.

A full roll-call of the combined mis-steps of Andrew and Fergie — the former Sarah Ferguson — includes inexplicable financial idiocies and a bizarre fondness for questionable associations with unsavoury characters.

If anyone had hoped that marriage might settle him down, his subsequent choice of wife merely amplified the uproar.

Long before he was swept up in the renewed Epstein manhunt, Andrew had displayed an uncanny talent for turning the most mundane of activities into bones of contention, be it the 2007 post-divorce sale of the Yorks’ Sunninghill Park home — at a curiously inflated price to the son-in-law of the ruler of Kazakhstan — or the birthday tea party he threw at Buckingham Palace for the daughter of David and Victoria Beckham.

His tenure as a roving envoy promoting British interests ended unhappily in 2011 after a series of controversies. Chris Bryant, a former Labour minister, later observed bleakly: “He doesn’t exactly add lustre to the royal diadem.”

What emerges most forcibly from this long list of mishaps is not so much that it is hard being a ‘spare’ (Andrew used to be second in line; now he is ninth). The bigger surprise was how easily Buckingham Palace swatted aside any suggestion of scandal as Andrew lurched on from being “Air Miles Andy” in pursuit of British trade to Pitch@Palace, his latest scheme for young tech entrepreneurs.

In a 2017 interview with The Sunday Times Magazine — two years after photographs emerged of the prince with Epstein following the financier’s release from a Florida jail — he declared himself an “ideas factory” and “the entrepreneur-in-residence” at the palace.

Palace Entrepreneur

He is much praised in the royal family for his devotion to his daughters, Beatrice and Eugenie, but one of his relatives was quoted as saying: “It’s about time he found something useful to do.”

Even that interview, intended to promote Andrew as a valuable member of society, went hideously awry. He proved strangely oblivious to a rare opportunity to display some personal charm, refused to pose for previously agreed photographs and brusquely shrugged off any suggestion of past mistakes: “You don’t get it right all the time … it doesn’t bother me. It’s just part of life’s rich tapestry.”

In retrospect it might have been better for someone to take him quietly aside and say: “This is a good chance to clear the air over that Epstein thing, maybe explain what you were doing in that house and apologise if you inadvertently hurt anyone.” But that, by most accounts, is not how he operates.

“Andrew’s association with Epstein is deeply damaging and he needs to deal with it,” said one source who knows the Queen. “This isn’t going away. There is a need for him to do or say something more than the statements that have been put out so far. Some kind of public behaviour which shows he has a bit of humility might help, but he hasn’t really got that streak in him.”

“Andrew’s association with Epstein is deeply damaging and he needs to deal with it.”

Another source added: “The Queen has always let Andrew do whatever he wants. They are close and he regularly visits her, more than any other members of the family. Everyone in the family seems to overlook his misdemeanours and he is given a lot of grace because of his daughters. But there is a feeling in some royal circles that Andrew should be slightly kept at arm’s length.”

One option might be for him to offer the FBI a voluntary statement as a possible witness against others alleged to have colluded with Epstein. He might face subpoenas from lawyers representing Epstein’s victims, yet submitting himself to an uncomfortable but conclusive grilling must surely be preferable to lingering doubt that might bar him from any form of future royal duty.

He has certainly done little to deserve a place in Prince Charles’s proposed slimmed-down monarchy.

“Andrew has done some good public duties, such as his work as a pilot, and can be good company,” said a source. “But he’s quite arrogant, with a tendency to blame other people when things go wrong instead of looking at his own behaviour.”