The shady side of Prince Andrew

Queen Elizabeth II famously dubbed 1992 the "annus horribilis" after both of her sons' marriages broke down, and Windsor Castle caught fire. But according to Express, 2019 will also go down in history as a particularly horrible year for the royal family. Her Majesty was pulled into the increasingly volatile Brexit debate, and the Duke and Duchess of Sussex were put under such intense scrutiny by the British tabloid press that they reportedly considered quitting royal life for good. The biggest blow came towards the end of the year, however, when Prince Andrew (who, by many accounts, is the queen's favorite son) gave a now infamous TV interview in which he attempted to explain his links to convicted sex offender, Jeffrey Epstein.

Prince Andrew was widely criticized after his sit down with BBC reporter Emily Maitlis at Buckingham Palace (Charlie Proctor, editor-in-chief of Royal Centralcalled it "a plane crashing into an oil tanker, causing a tsunami, triggering a nuclear explosion"). The backlash from the interview was so bad, Prince Andrew made the shocking decision to "step back from public duties for the foreseeable future." 

But, was it just the Epstein scandal that landed the Duke of York in this mess? He may be a Falklands War vet who has done his fair share for charity, but there's no denying that he has a sketchy past. Here's everything we know about Prince Andrew's shady side.

How did Prince Andrew get the nickname 'Randy Andy?'

Prince Harry had a reputation as a hard partying prince before he settled down with Meghan Markle, but he wasn't the first royal with a rebellious streak — and he wasn't the first royal to fall hard for an American actress, either. Harry's uncle, Prince Andrew was dubbed "Randy Andy" by the British press in his younger years. Before he married Sarah Ferguson in 1986, Prince Andrew dated actress Koo Stark (pictured above), who filmed scenes for Star Wars that were later cut. According to The Sun, the prince introduced Stark to his family and the pair nearly married until it emerged that Stark "had starred in an erotic art film called Emily in 1976." After the revelation, they were forced to part ways.

After his divorce from Ferguson, Prince Andrew had what Vanity Fair described as "a procession of girlfriends," some of whom have opened up about their time with the prince. One of them even told the outlet that Prince Andrew "liked to model her underwear as a joke" when the two were alone together, though (thankfully) no pictures of this have ever emerged. There are, however, lots of snaps of the Duke of York partying with different women, from Canadian socialite Pascale Bourbeau to German supermodel Heidi Klum. His Royal Highness claimed that he wasn't into PDA during his disastrous BBC interview, though snaps obtained by The Sun seem to prove that this isn't the case.

Did Prince Andrew try to hook up with Courtney Love?

It's hard to imagine a member of the royal family hanging out with Courtney Love, but there's photographic evidence that a meeting between Kurt Cobain's ex and Prince Andrew took place. The Duke of York supposedly got Love's address from a mutual friend, and showed up at her house hoping that she could show him a good time in Hollywood. "I was in bed when the doorbell rang at 1am, so put on my fluffy slippers and a dressing gown, and the Queen's second son was standing there with a protection officer, totally unannounced," Love told a friend, according to The SunThere's no indication that anything went down between the royal and the rocker, though it reportedly wasn't down to a lack of trying on the prince's part.

"He seemed to be looking for sex and was quite flirtatious," Love apparently told her friend. "We sat down on the sofa, by the fire, and that is when he got quite flirtatious." Love reportedly served the Duke of York tea in "a vintage china cup" with his mother's face on it, which, as you can imagine, probably killed the mood. "In the end he only stayed for around 45 minutes. Of all the things that have happened in my life, this truly is one of the most surreal things — and that is saying something." A picture supposedly taken during this bizarre meeting was published in Love's memoir, Dirty Blonde.

Prince Andrew's dodgy dealings

In 2001, Prince Andrew was named as Britain's "special representative" for Trade and Investment. He stepped down from the role in 2011 after a series of controversies made it impossible for him to carry on. The discovery of his friendship with convicted sex offender Jeffery Epstein was the beginning of the end according to the BBC's royal correspondent Peter Hunt, though other aspects of the Duke of York's shady behavior had been under scrutiny for some time. Among his many questionable moves was dealing with Timur Kulibayev (the sketchy son-in-law of the President of Kazakhstan), who purchased a property owned by Andrew for several million more than its asking price.

The sale of his Sunninghill Park home certainly raised eyebrows, but it wasn't until his ex wife was secretly recorded by an undercover reporter that he was deemed wholly unsuitable to be Britain's trade envoy. In 2010, Sarah Ferguson was the subject of a sting by the now defunct tabloid News of the World. She was filmed asking for a payment of half a million pound in exchange for access to Andrew. "That opens up everything you would ever wish for," she told an undercover reporter (via The Guardian). "I can open any door you want... Look after me and he'll look after you."

Andrew denied having any knowledge of this, though Fergie was on tape telling the undercover reporter he knew about the dodgy meeting and had even suggested the amount of money she should ask for.

Prince Andrew's travels aren't cheap

Prince Andrew's popularity plummeted during his time as a special trade envoy for Britain. According to a document unearthed by WikiLeaks (via the BBC), a U.S. ambassador said that the prince's attitude "verged on the rude" during official engagements, but public opinion was also bleak, thanks in no small measure to his expensive, state-paid travel habits. The queen's second son earned the nickname "Air Miles Andy," because he routinely opted to fly to meetings when cheaper transportation options were available.

There was a public outcry in 2009 when it transpired that Andrew had used his mother's helicopter to make the short trip from Windsor to Kent, which takes a little over an hour by car. Anger reached boiling point after it was discovered that he attended a party at a golf course while there. "The helicopter is very often the most efficient way of packing in as many engagements as we can," Andrew said (via the Express). "It enables us to see more people all over the country, do more things and get better value for time and money out of my role as Special Representative."

The British taxpayers didn't see it that way, but their protests never discouraged him. Even after he stepped down as trade envoy he continued to use choppers unnecessarily — in 2016 he flew from London to Norfolk at a cost of around $3,850, a journey that would have cost just $45 by train, according to the Daily Mail.

Is Prince Andrew really 'the worst end of the royal family?'

Prince Andrew has been accused of using racist and offensive language on more than one occasion. According to former Labour Party home secretary Jacqui Smith, the Duke of York "made racist comments about Arabs" during a state dinner for the Saudi royal family, who are long-time allies of the United Kingdom. Speaking on a podcast that she now co-hosts, Smith recounted the prince's allegedly controversial comments. "I met him several times, including once at a state banquet where after dinner, I and my husband and another Labour cabinet minister had a drink with him, and I have to say the conversation left us slack-jawed with the things that he felt it was appropriate to say," she said (via the Independent).

Smith refused to repeat exactly what the prince had actually said on her podcast, though she did reveal that it "involved a comment about camels" and was "as worse as you could imagine." She added, "The fact he thought we might find this amusing was sort of a terrible situation to be in. I don't think he's very bright. I don't think he really understands the way in which he behaves. He's the worst end of the royal family, I think." 

A representative of Buckingham Palace responded to Smith's accusations by lauding Prince Andrew's "work in the Middle East," and claiming, "He does not tolerate racism in any form."

Prince Andrew was accused of using the n-word

The royal family has been praised for embracing diversity ever since Meghan Markle (whose mother Doria Ragland) is African-American) joined the Firm, but some shocking revelations from businessman and columnist Rohan Silva threaten to derail all that. Silva, who was once an aide to former British Prime Minister David Cameron, penned an explosive piece for London's Evening Standard in 2019, alleging that the Duke of York used a racial slur during a meeting with him.

Silva, who is of Sri Lankan descent, was left stunned after his first encounter with the duke. The pair were discussing EU spending when Prince Andrew reportedly interrupted him and said: "What you have got to remember is that you'll never get anywhere by playing the white man." He reportedly went one step further during their second meeting in 2012. Silva claims that he and Prince Andrew were discussing how the trade department "could be doing a better job" when the duke piped up and said: "Well, if you'll pardon the expression, that really is the n***** in the woodpile." Silva said he was left "reeling" from the comment, and later regretted "not confronting the prince on his choice of words."

According to the Evening Standard, this out-dated, deeply offensive phrase originated in the Deep South of the U.S. and refers to African slaves who "hid in piles of logs as they fled north to Canada." Royal representatives have "categorically denied" Prince Andrew's use of the phrase. 

Prince Andrew's friends reportedly warned him about Jeffrey Epstein

When Vanity Fair ran an article entitled "The Trouble with Andrew" back in 2011, the mag interviewed a friend of the Duke of York, who claimed that the royal ignored his warnings about Jeffrey Epstein. The insider said that he told Prince Andrew to end his relationship with the American financier after he pleaded guilty to a felony charge of solicitation of prostitution involving a minor in 2008. Instead, Prince Andrew reportedly called his pal a "puritan" and told him to "stop giving [him] a hard time" over Epstein, who was found hanged in his jail cell in 2019.

The insider continued, "From there, our conversation descended into a screaming match. Finally Andrew said, 'Leave me alone. Jeffrey's my friend. Being loyal to your friends is a virtue, and I'm going to be loyal to him.'" That loyalty backfired spectacularly after the Duke of York visited Epstein in New York in 2010, after Epstein's release from prison. The two men were pictured on a stroll through Central Park together.

After Epstein was arrested and indicted for sex-trafficking charges nine years later, Prince Andrew claimed that he only went to see Epstein to break off their friendship. "[Andrew] has apologized again and again for the error of judgment," a source close to the prince told The Sunday Times, adding, "But what he did wasn't criminal. It was a mistake."

Prince Andrew apparently has a 'stubborn streak'

The same friend that reportedly advised Prince Andrew to cut ties with Jeffrey Epstein before it came back to bite him in his royal backside also told Vanity Fair that the prince has a "stubborn streak" that often gets him into trouble. "He does stupid things out of hubris, to show that he can do them," the insider said. "If he likes someone, he'll ignore the truth about that person. And that goes both for Jeffrey [Epstein] and Sarah [Ferguson]. He thinks that he can power his way through everything."

According to the prince's pal, this attitude has been fostered by his mother. "He's an adored second son," the source said. "The Queen dotes on him, favors him above all her other children, and excuses his every foible." Another well-placed royal insider told the Daily Mail that the prince "can do no wrong" in the queen's eyes. "He always greets 'Mummy' in the same way — bowing from the neck, kissing her hand, and then kissing her on both cheeks. It's a little ritual that she adores."

He might be a mother's boy, but one person who apparently doesn't stand for his behavior is his older brother. In September 2019, Prince Charles reportedly had to step in when Andrew lost his temper with a highly respected palace aide. "There were heated words on both sides," a source told the Daily Mail. "The duke got very cross that what he wanted wasn't possible."

Prince Andrew: His Royal Dryness

The Duke of York attempted to stem the flow of bad press surrounding his affiliation with convicted sex offender Jeffrey Epstein by granting an interview with BBC Newsnight. It didn't work. Attempting to answer questions head on, all Prince Andrew did was raise more questions and leave himself wide open to mockery.

Alleged Epstein victim Virginia Giuffre (née Roberts) claimed in court filings (via the BBC) that she was "forced to have sex with the prince on three occasions." The queen's second son claims to have no memory of meeting Giuffre, despite the fact that a picture of him with his arm around her waist has been circulating online for years. "We can't be certain as to whether or not that's my hand on ... her left side," he told Newsnight, adding that "nobody can prove whether or not that photograph has been doctored."

Giuffre, who was only 17 years old when one of their alleged encounters took place, claimed that Andrew was "profusely sweating" when they danced together at a London nightclub. Andrew claimed this wasn't possible, citing medical reasons. "I didn't sweat at the time, because I had suffered what I would describe as an overdose of adrenaline in the Falklands War when I was shot at," the royal said. Medical professionals, however, quickly cast doubt on the dubious claim. Saying he was "absolutely skeptical," Good Morning Britain's Dr. Hilary said (via the Mirror), "Sweating isn't mediated by adrenalin, it's mediated by acetylcholine."

Prince Andrew's alibi is all kinds of shady

During Prince Andrew's uncomfortable interview with Emily Maitlis of Newsnight, he provided the decidedly shady alibi that he was at a Pizza Express (a chain of restaurants in the United Kingdom) on the night that Virginia Giuffre claims they had sex. The prince said that he had taken his daughter, Princess Beatrice, to a party at the restaurant that evening and then returned home. When Maitlis pointed out that this was an odd thing for the royal to recall so specifically, he agreed.

"Going to Pizza Express in Woking is a very unusual thing for me to do ... I've only been to Woking a couple of times and I remember it weirdly distinctly," the duke said. "As soon as somebody reminded me of it, I went, 'Oh yes, I remember that.'" Critics have pointed out (via the Express) that high ranking royals keep "protection records," and therefore Prince Andrew would be able to use these to categorically prove that he was indeed in Woking that evening, but he has so far failed to produce these records.

The branch of Pizza Express that the prince claimed to have visited was later inundated with spoof reviews after the disastrous interview aired. "The pizza is so good from this specific branch it gives you the ability to not only remember what year you visited, but the exact day and month," one review read (via Metro). "Truly incredible."