Prince Andrew didn’t even make the cover lines on the October 18, 1976 issue of People magazine. (That was Captain & Tennille.) He was just 16 years old, and the focus was his relentless and—at that point—appropriately juvenile practical joking: “On some distant and solemn day, when Prince Charles is crowned king of England, he had better check his throne very carefully before sitting down. If his younger brother, Prince Andrew, is around, chances are a whoopee cushion will also be in the vicinity.”
By 1984, when he was 24 years old, Prince Andrew had acquired a bit more of a sheen, between his military service in Britain’s short-lived Falklands conflict and, of course, that title: “Would Prince Andrew find a Cinderella in Hollywood? That was the premise waiting for a script during His Royal Highness’ four-day stay in Los Angeles,” People asked, noting his flirtations with one woman in particular. That was the lead, anyway, before the loutishness reemerged, in an anecdote about how Andrew turned around during a tour of an abandoned house in Watts and sprayed the press corps following him with a paint compressor. Estimated damages: $20,000.
Prince Andrew has been something of a punchline for much of his adult life. The fairy tale role of Prince Charming has loomed large over him, but he’s never fit it, opting instead for puerile humor and blatant entitlement, never quite managing to deploy the kind of careful condescension in which royals like his nephew William are so skilled. Instead, Andrew has played the part of the “Playboy Prince,” known for decades in the tabloids as “Randy Andy,” almost a stock figure of buffoonish privilege straight out of a pantomime or an 18th-century satirical print.
But the name and the antics read very differently in light of the Epstein revelations, however, including the latest appalling details from the unpublished memoir of accuser Virginia Guiffre. Guiffre, who alleges that Epstein forced her to have sex with Andrew three times when she was 17, describes Andrew as groping her and another young woman at Epstein’s house with a puppet of himself from the satirical British program Spitting Image, the chilling echo of those early stories about practical jokes. The “Randy Andy” now seems like a case of the truth hiding in plain sight—a lesser charge that for years after Epstein’s conviction kept the Duke of York firmly in the realm of ridiculous rather than criminal.
Andrew was born in 1960, the third of Elizabeth and Philip’s four children. There’s nearly a full decade’s gap between Andrew and Anne, his next oldest sibling, and the children came at totally different points in their mother’s life. Charles and Anne were born when Elizabeth was taking on an increasing amount of responsibility for her father. When he died and she was elevated to the throne with unexpected suddenness, they were still small children, leaving her juggling parenthood and a job on the world stage. (With a small army of domestic help, of course.)
In contrast, Andrew was born when she was well-established in her role, and she took more time with her next two children: “Early in the 1960s, Her Majesty decided that she had done her duty by her country, and took the best part of eighteen months off work to produce and enjoy her ‘second family’, the young princes Andrew and Edward, born in 1960 and 1964 respectively,” historical advisor to The Crown Robert Lacey told Town and Country. And, too, Andrew was reportedly a cheerful, uncomplicated child: “Queen enjoyed the company of the easy-going son who could make her laugh and raise the family’s spirits,” Camilla Tominey at the Telegraph wrote in her assessment of Andrew’s fall. It’s long been rumored that the Queen has a special fondness for Andrew—a rumor that puts a pall on her current late-life popularity.
Andrew was raised in a princely splendor that even William and Harry wouldn’t recognize, as a friend pointed out in the Telegraph piece: “His nappies would have had royal crests on them.” His doings were, for instance, tracked in the New York Times beginning with front-page coverage of his name at birth: “Prince Andrew, 2, Has Party”; “Prince Andrew, 4, Begins School With 4 Playmates”; “Prince Andrew Will Get Midget James Bond Car.”
But he was always the spare, not the heir, and with the arrival of William and Harry in the early ’80s, he was knocked even further down the pecking order. He had a brief, shining flash of heroism in the Falklands War, where he served as a helicopter pilot. “If anything happened to him over there, there’d be an outrage, you can bet,” a bus driver in a pub told the New York Times for a piece about the conflict. He was treated as a serious voice from the conflict and greeted as a hero upon his return—the classic younger son shut out from the big-ticket inheritance but nevertheless distinguishing himself and his family with his military service in one of Britain’s colonial wars.
But he was even more famous as the “Playboy Prince”—or “Randy Andy,” as the tabloids took to calling him with their instinct for the jugular.
Most famously, mere months after his much-ballyhooed return from the Falklands, the British press flipped out upon realizing he was dating an American named Koo Stark, whom People described as a “soft-core actress,” adding that, “Pictures of a nude and saucy Koo in lascivious poses were splashed over tabloid front pages.” The press hounded her. (She’s worked as a photographer since the 1980s.) This was a piece of nuclear-hot gossip, of course, and it was unquestionably Stark who was portrayed as the dirty one. “It is one thing for a prince to be seen with a film actress, but quite another to go away on holiday with a blue movie star. The Queen feels badly let down,” a palace staffer told the press when the pair went on vacation to the Caribbean.
But the prince half of the “Playboy Prince” moniker won out—for a while, anyway. Apparently, the paint-spraying was a turning point: Vanity Fair reported in 1986 that Andrew got a “furious transatlantic telephone call” from his father afterward, and he was basically grounded when he got home. “Royal-imagemakers were instructed to spray a little white paint over Andrew’s tarnished reputation,” as Vanity Fair put it. He broke it off with Koo Stark. And then came the perfect next step: an engagement to Sarah Ferguson, the perfect opportunity to cast him as not merely the fairy tale prince, but even a bit of a reformed rake. The pair were married in an echo of Charles and Diana’s marzipan fairy tale nuptials of a few years earlier, with similarly enthusiastic international press coverage. “THE JOLLY ROMANCE,” declared Vanity Fair. “He’s jolly nice, she’s jolly nice, and they’ve jolly well decided to spend the rest of their lives being jolly together.”
The jolly was short-lived. Andrew and Fergie’s marriage ended in a tawdry manner, with Fergie essentially iced out of the family after the tabloids published the infamous “toe-sucking” photos, an important moment in the royal family’s 1990s nadir. Even by the messy standards of the Windsors that decade, it was bad, because it wasn’t just tawdry—it was vulgar. But again, much of the attention was on the woman: Fergie’s problem was what seemed at first like refreshing informality had quickly soured, revealing her as insufficiently posh. (Fergie cashed in in America, doing work for Weight Watchers, Wedgwood, and even Ocean Spray.)
It was a bad decade all around for the family, from the public revelation that Charles had once wished to be Camilla’s tampon to Diana’s horrifying death in Paris, which made the family look glacially cold. But finally, the Windsors pulled themselves together and collectively embarked upon the process of remaking themselves for the new millennium. Charles rehabilitated himself and Camilla too, his office carefully burnishing her image until they could marry and remake themselves into a pair of smiling British grandparents. William and Harry grew into teenage heartthrobs. The Queen herself gained new respect as a dutiful living link to the wartime era that so obsesses the United Kingdom. And Andrew—supposedly—got more serious as he hit middle age. Or at least that was the story.
In 2000, People was back with a profile of the prince, headlined “Midlife makeover.”
A royals correspondent for Britain’s Press association told People that the Palace saw Prince Andrew as “a good way of improving the royal family’s standing among members of the public” in the wake of Diana’s 1997 death. “Suddenly, Andrew has blossomed and matured,” said Tatler magazine editor Geordie Greig. Another friend said, “He is beginning to stand on his own two feet.” (Andrew had just turned 40.) He was working for a child abuse prevention initiative, Full Stop, as well as holding down a liaison job in the Navy and accepting a gig as president of the Football Association. Not long after the story ran, Andrew retired from the Navy and received an appointment as a U.K. trade envoy.
But even before the Epstein allegations resurfaced, this narrative of the more somber middle-aged Andrew didn’t hold water for very long. A 2011 Vanity Fair piece titled “The Trouble with Andrew” outlined his many, many missteps over the decade that followed, from bad judgment—he once took a helicopter a mere 50 miles to meet with visiting dignitaries—to just plain sketchiness: “Andrew dined with Nursultan Nazarbayev, the corrupt president of Kazakhstan, whose son-in-law subsequently bought Andrew’s white-elephant mansion, Sunninghill Park, for $25 million, $4.9 million more than the asking price. (Buckingham Palace denied that there was any impropriety involved in the sale.)” Stories abound of his acting entitled, boorish, and just plain rude. He once reportedly rammed his own park gates at his Windsor home with his £80,000 Range Rover because he didn’t want to drive a mile out of his way and they wouldn’t open. “He has a bit of a reputation for roaring around like Toad of Toad Hall and seems to think he can do what he likes,” a source told the Telegraph.
But in light of the Epstein allegations, that “midlife makeover” looks even worse. It in fact mentions Ghislaine Maxwell by name as a woman Andrew has been seeing, and contains this bit of party reporting that is absolutely chilling in 2020:
Even during his three-day visit to the Big Apple Oct. 29-31, he squeezed in some nightlife. Attending a Halloween costume party hosted by model Heidi Klum at the chic Hudson Bar, the teetotaling Andrew sipped bottled water and chatted with Maxwell, who wore a leopard-print jacket and platinum wig, as well as with Donald Trump and his girlfriend, model Melania Knauss. “He’s not pretentious,” says Trump. “He’s a lot of fun to be with.” Maxwell seemed to think so too. She and the duke, who have been romantically linked since April, “seemed like coconspirators—talking, laughing and enjoying the party,” says one observer. “They were together the entire evening.”
Guiffre alleges that she was trafficked to Andrew in 2001, the year after this article appeared. “I grew up watching Disney movies and princesses and princes were the good people of the world. And he wasn’t,” Guiffre said in a television interview. A former employee of Epstein’s told the Sun that she once wandered into a room in Epstein’s mansion and found the man and Maxwell watching Andrew on videotape with a topless woman: “Ghislaine said, ‘Oh that’s Randy Andy for you,’” adding that Epstein laughed in response.
“That’s Randy Andy for you” sums up Andrew’s entire life in the public eye. It was clear that he was no heroic figure, neither a great intellect nor a solid workhorse with a keen sense of duty. But at the same time, the stereotype of the harmless skirt-chaser protected him from being charged with anything worse, hiding him in plain sight.