Jeffrey Epstein, the most notorious fornicator of our era, said of Prince Andrew – younger brother of the King and at one point second in line to the throne – ‘We are both serial sex addicts. He’s the only person I have met who is more obsessed with p***y than me.
‘From the reports I’ve got back from the women we’ve shared, he’s the most perverted animal in the bedroom. He likes to engage in stuff that’s even kinky to me – and I’m the king of kink!’
The nickname ‘Randy Andy’ was given to him at Gordonstoun, his public school, and earned because he was already sexually experienced, good looking and a girl magnet. And it stuck.
When he was the handsome young prince returning from piloting a helicopter in the Falklands War and pursued by scores of swooning girls, for whom HRH stood for ‘His Royal Heartthrob’, it was even a term of roguish endearment. Not any more.
Now in his mid-sixties, he is supposed to have slept with over a thousand women. ‘He’s shagged porn stars, actresses, models, athletes, politicians and bartenders at clubs,’ claimed investigative journalist Ian Halperin.
According to a friend: ‘Sex is his big thing in life. Travelling all over the world as the UK trade ambassador and for other royal duties has given him access to some beautiful women and he’s taken full advantage.’
A Reuters correspondent reported that, when Andrew represented the British monarch at the King of Thailand’s diamond jubilee celebrations in 2006, more than 40 women were brought to his hotel room in Bangkok during his stay: ‘Often, as soon as one left, another would arrive.’
Hotel staff were used to foreigners bringing in girls, but amazed that more than 10 a day were going to Andrew’s room.
One 20-year-old model realised how sex-obsessed he was after meeting him at a charity function in the late 1980s and sleeping with him twice at a hotel before being whisked off to the Caribbean island of Mustique.
‘He wanted me to engage in kinky sexual activity,’ she remembers. ‘He had no boundaries. He told me he had an open marriage arrangement with his wife. After returning to London, I never heard from him again. I felt like he used me for a few days, so he could live his wildest fantasies.’
Prince Andrew represented the British monarch at the King of Thailand’s diamond jubilee celebrations in 2006 and more than 40 women were brought to his hotel room in Bangkok during his stay, writes Andrew Lownie
Malcolm Barker, who worked at Buckingham Palace, remembered how Andrew was ‘for ever dragging the worst bunch of tarts up to dine with his mother, each seeming to compete with the previous for lack of brains. The one characteristic his girlfriends did not lack though was ample breasts.’
He was photographed on a luxury yacht off the coast of Sardinia, owned by an Egyptian millionaire friend, having sun cream rubbed on him by a 25-year-old Spanish-Filipina model, Alexandra Escat, nicknamed ‘the totty on the yachty’. (She denied any romance, saying they had been talking about military history.)
He entertained swimwear model Monika Jakisic, known as the ‘Croatian Sensation’, on his 54th birthday at the Italian restaurant Cecconi’s, then at the Arts Club in Knightsbridge, and a few weeks later in a private room at the Royal Thames Yacht Club. (After she posted a photograph on Twitter of what appeared to be a diamond engagement ring, his press agent was forced to deny the rumour.)
Nor were staff out of bounds. There was a long-standing rumour of an affair with a household staff member when he was still married to the Duchess of York. One nanny left because he made unwelcome advances.
‘When I started,’ an employee remembered, ‘I was warned to stay away from him. He would sometimes enter the staff quarters. It seemed everyone was aware of his behaviour, but little was done about it.’ The employee added: ‘Staff gossiped all the time, but a tape device was found in a flowerpot in the staff area, so it was difficult to speak after that.’
According to Emma Gruenbaum, a masseuse at the Wentworth Golf Club that Andrew frequented, he often booked her for massages at Royal Lodge, his home in Windsor Park but ‘it always felt a bit sleazy. It was clear he wanted more’.
Andrew insisted on being naked and, despite her objections, the massage taking place in his bedroom. He would try to hug her and ask about her sex life. On one occasion, while she adjusted the massage table, he remarked, ‘Hey, nice ar**e. Do you take it up the a**e?’
She remembered how ‘all the way through he was talking about anal sex and making anal sex jokes. He asked when I had last had sex. It went on and on. That’s just not normal behaviour for a professional sports therapy session. He was a constant sex pest from the start.’
He has never had trouble picking up women, but, a family friend said: ‘He’s not a hunter of women. He rather expects them to come to him. But when they do, he shows himself to be bone idle and not very socially adept at chatting them up.’
According to a source, he likes to have his women handed to him on a plate, ‘and the shorter the skirt the better’. Friends acted as matchmakers. Otherwise he would use his staff. He would spy out an attractive ballerina at the Royal Ballet and then send one of them to the stage door to invite her to meet the prince.
Other variations included sending aides to invite girls to his table at the Chinawhite night club in London or come to his hotel suite when abroad.
‘He’s about as subtle as a hand grenade,’ according to one girl he propositioned. ‘His favourite trick is to rub your knee under the table. It’s pathetic.’
At a wedding he was said to have asked a woman he’d not met before for a dance. When she declined, he responded, ‘I suppose a b*** j** is out of the question, then?’
One of his many flings told how their encounters would frequently involve little more than a telephone call from him, a trip by her to an off-licence for a bottle of champagne, a taxi ride to Buckingham Palace, ‘a perfunctory act of love and a muttered goodbye’.
But the ‘sad truth about Andrew’, one of his lovers claims, ‘is that he is not a Casanova at all. Let’s just say that in the bedroom department he is a bit of a let-down. He has been dumped by most of the girls linked to him because he is a bore.’
Few of his relationships have lasted, partly because he has a low attention threshold and partly because women quickly tire of him. Though many have dumped him, when he does so himself it is ruthless. He simply does not take their calls.
From the start, Andrew’s behaviour has excited disapproval. ‘A very slimy so-and-so, arrogant, pleased with himself, a bully’, was the verdict of one female contemporary at Gordonstoun. ‘He was so full of himself. He would throw his weight around and often say “You do know who I am?” ’
According to a friend: ‘Sex is his big thing in life. Travelling all over the world as the UK trade ambassador and for other royal duties has given him access to some beautiful women and he’s taken full advantage’
Then there were his japes. She remembers camping one November in the grounds of Balmoral and Andrew, then 18, ‘ripping off the flysheets of the tents and throwing them into the river for fun’. She adds: ‘He thinks he’s funny, handsome and clever and he isn’t. He swaggered around but all the cool boys of his age thought he was a wally and a t****r.’
His favourite activities at parties were playing ‘choo-choo trains’, where everyone danced around the room in a conga shouting ‘choo-choo’, or games in which pieces of fruit were passed from under one person’s chin to the next.
One friend of his admitted: ‘He’s a nightmare to sit next to at dinner. He makes ghastly jokes about whether you’re wearing knickers. And you can’t tell him to sod off.’ They added that his jokes were so ‘lavatorially disgusting everyone was aghast’.
One of his dates said: ‘He tells the most pathetic jokes. He finds poo cushions funny.’
Prince Edward, after his then girlfriend Romy Adlington had accepted an invitation to go duck shooting at Sandringham in 1983, warned her: ‘The bad news is that you might have to drive up with my brother!’ And so it proved, with Andrew joking about farting and asking her: ‘Don’t you find they always smell worse when you do them in the bath?’
No wonder that a titled lady of his generation said: ‘He is easily the most boorish man I have ever met.’
A strong and juvenile characteristic of his is to take advantage of his position to humiliate others who may not be able to respond. At a society event in 1992 he unzipped broadcaster Tania Bryer’s evening dress the full length of her back.
His idea of fun is to get guests at parties to close their eyes then place an open tube of mustard between their outstretched hands and get them to clap. ‘The spectacle of someone receiving a faceful of mustard gives him great joy,’ said a source.
At one dinner party he sniffed the pâté served as first course and turned to his right. ‘This pâté smells. What do you think?’ His female companion leaned forward to smell it and he promptly pushed her face into the dish.
Sometimes, partly from boredom or mischievousness, he simply wants to provoke a reaction. There is the story of how he once walked into a room where people were watching TV. He changed channels, paused, then walked out.
Andrew has always had a strong sense of status but been unsure otherwise of his identity. As a child playing on the decks of the Royal Yacht Britannia, when addressed as ‘laddie’ by a sailor, he replied to the much older man, ‘I’m not a laddie, I’m a prince.’
And this problem of deciding when he is a prince and when he is a normal person has bedevilled his whole life. After a house party in Dorset, one young woman complained: ‘One minute you’re having your bum pinched and the next minute he’s reminding you he’s Your Royal Highness.’
One of his dates recalled how he always introduced himself to her friends as the Duke of York, ‘even when we were dancing on tables at two in the morning at Momo. It struck me how impressed he was with who he is, or how impressed he wanted others to be.’
Once playing golf in a group of four, Andrew hit an especially good shot on to the green. One of the other golfers said: ‘Good shot.’ The prince fired back instantly: ‘That’s good shot, sir, for you.’
If he walked into a room and people didn’t acknowledge his presence, he’s been known to clear his throat, say, ‘Let’s try that again’, leave the room and come back to make sure everybody stands, bows and curtseys.
Andrew was photographed on a luxury yacht off the coast of Sardinia with 25-year-old Spanish-Filipina model Alexandra Escat in 2010
He could be unbelievably cruel. In 2005 after a heavy storm at Hillsborough Castle, Andrew asked the head of the household, David Anderson, if there was any damage. ‘Yes, sir,’ responded Anderson. ‘The tree which was planted by the Queen Mother.’ This was followed by a withering silence, then Andrew said in a mocking voice, ‘Did you mean Queen Elizabeth the Queen Mother?’
He then asked the poor man how long he had worked for the Royal Family. Anderson replied, ‘I joined in 1984, sir.’ ‘And you still don’t know the proper way to refer to my grandmother? You f***ing imbecile. Get out.’
The prince has remained totally out of touch with reality. Lucy, a former stylist who dated him, was surprised that when she offered to take him to the cinema and said she’d buy the tickets, he expected her to get all seven, to include his security.
Everything revolves around Andrew and is about him. In this, he reminded the journalist Petronella Wyatt, who first met him at a society party in the 1990s, of Princess Margaret, ‘who thought she was more royal than the Queen. He talked and you had to listen. He ignored all attempts to change the conversation and continued to make inappropriate jokes. He’s the most out of touch royal I’ve ever met and I’ve met lots. He really does believe in the Divine Right of Kings.’
One woman who met him at a party in Saint-Tropez said: ‘He doesn’t have much conversation other than himself.’ The wife of a former naval colleague remembered that all he could talk about was how you could tell the difference between a real Rolex and a fake: ‘The fake ticks, the real one swishes.’
Awkward in company, he finds it hard to relate to people and has few friends.
His former girlfriend Koo Stark’s marriage to Green Shield Stamps heir Tim Jefferies in 1984 deeply unsettled him. He admitted to a friend: ‘I am a loner – I really am. Yet when I say that, no one believes me. I’d really like to be married but I’ve yet to meet the right girl.’
Ian Hendry, a fellow naval cadet with Andrew at Dartmouth Naval College, found him a bit remote and thought he compensated for shyness by being over-ebullient: ‘He puts on his royal hat to protect himself, that’s his veneer.’
Hendry cast him as a slightly lonely figure who didn’t really know how to make friends: ‘He was confused how to behave as he moved between the naval and royal world. Barriers were put up as a coping mechanism and he became bombastic.’
Another cadet who served with the prince and twice got lifts to London in his police escort got to know Andrew slowly because he was such a loner, but also found him a strange mix – someone who did not appear to feel relaxed about his position as prince. Andrew was not naturally good at making friends. He would relax then stiffen up: ‘He wasn’t a person with whom one could get close.’
In 2021, after Meghan Markle was accused of bullying staff, Buckingham Palace braced itself for historic complaints about Prince Andrew’s bullying, profanities and impossible demands.
A former aide had been reduced to tears after being ‘bawled at’ in a phone call before dawn because Andrew was unhappy with a story in the Sun newspaper. A member of staff was moved to other duties because Andrew ‘disliked a mole on the man’s face’, another ‘because the man was wearing a nylon tie’.
Some say a report on bullying accusations against Meghan Markle has never been released because it would also raise questions about the behaviour of the Queen’s second son.
The way Andrew treated staff caused one royal aide to describe him as ‘a deeply unpleasant man’. Colin Burgess, who served as equerry to the Queen Mother for many years, felt he was treated with disdain by Andrew, in ‘stark’ contrast to the respect for staff shown by Prince William and Charles, the then Prince of Wales.
For Charles, the Queen Mother’s staff were her companions, but to Andrew they were just employees. ‘I saw him about once a month when he came to visit Clarence House, and he would talk to the staff, including me, as an officer talks to his subordinates,’ said Burgess. ‘He would say things such as: “I want this done, and I want it done now”. “Do it!” was his catchphrase.
‘I remember nearly telling him where to go when he came into Clarence House and wanted something wrapped. He looked at me and barked, “You, wrap that!” And pointed to some object. I just thought, you rude, ignorant sod, and felt like decking him. In all honesty, he wasn’t a particularly nice person.’
Because the duke, pictured kissing a woman in the sea off Corsica in 2011, has never been disciplined, Andrew Lownie writes, he knows he can behave exactly as he wishes
Because Andrew has never been disciplined, he knows he can behave exactly as he wishes. A favourite game was to insist on driving himself and then deliberately lose the back-up protection car by speeding up the motorway and suddenly turning off onto a side road.
His protection officers were called on to collect his golf balls after he had driven them down the fairway, and maids summoned from four floors below to open the curtains beside him. He once called a television technician at night to show him how to work the remote control on a TV set.
Wendy Berry, the housekeeper at Highgrove whose son worked at Buckingham Palace, noted that for the duke, staff were basically invisible, ‘there to serve and not to question his actions’. His thoughtlessness upset most of the housemaids and valets who worked for him.
‘Apparently his bedtime habits as a single man left a lot to be desired,’ she said. ‘A collection of scrunched-up, soiled tissues usually lay scattered around the bed each morning for staff to collect after they had made his bed.’
Andrew has always felt the rules did not apply to him, starting at Heatherdown, his prep school, when a box of exotic stamps went missing. After a search they were found in his desk. According to one of his classmates: ‘He had crossed out the name of the owner and put his own name on it. When discovered, he simply shrugged it off.’
Stories abound of him being banned from golf clubs because he ignored club rules on the use of mobile phones.
In October 2005 he refused to go through a security scanner at Melbourne Airport on a private visit, claiming that ‘lack of respect’ had been demonstrated. A security worker said: ‘What a pompous prick. Everyone has to go through screening. He should be happy to do so and set an example.’
And there is a history of road incidents. In 2002 he was stopped by police for speeding at 60 miles an hour in a 40mph area, rushing to catch a plane to Scotland to watch the Open golf championship. The offence carries a minimum fine of £60 and three penalty points, but Andrew was let off on the grounds that ‘I’m in a hurry’.
On another occasion he had an accident driving his Range Rover near Borehamwood. His protection officer took the blame. In July 2009 the Windsor Park lodge keepers signed a petition to the Queen, complaining about Andrew speeding through the park in his Aston Martin and ‘forcing them to leap out of the way as he zooms past’.
Travelling to Royal Lodge in March 2016 in his £80,000 Range Rover, he found the gates’ sensor in Windsor Great Park broken. Instead of taking a mile detour, he rammed the gates open, causing thousands of pounds’ worth of damage – money that ultimately came from the taxpayer. A Windsor worker likened him to Toad of Toad Hall, who thinks he can do what he likes.
And he gets away with it. He hit a policeman as he sped into Buckingham Palace. The uniformed officer suffered an arm injury and complained to his bosses, but nothing was done.
Nothing was done either when he was playing in an exhibition golf match at The Belfry in 1998 and hooked his drive into a bunker. According to an observer, he took a quick look at his ball, didn’t fancy the lie, picked it up and threw it sideways onto a better one. Such an act called for at least a one, or possibly a two, stroke penalty but nobody said anything.
His arrogance is breathtaking. A friend of his once had a lift in his chauffeured car with police escort from Buckingham Palace to Canary Wharf. With all the traffic stopped, the journey took under eight minutes. The friend asked Andrew if he felt embarrassed that everything had to stop for him. ‘Oh no, people don’t seem to mind at all.’
One day a train taking the duke to Birmingham was cancelled and he was told he could wait in the VIP lounge for the hour until the next one departed. He was furious, venting his rage at his equerry. ‘Why can’t they organise another one?’ He flicked his hand and shouted: ‘That train over there, for example, why can’t they divert that train to Birmingham?’
Another time Andrew asked to have lunch with Boris Johnson, when he was Mayor of London, turning up with a list of things he wanted to talk about. He wanted to redesign traffic lights with ‘fewer red lights’. He thought the whole of Battersea Power Station should be demolished, including the listed towers. He felt the Queen Elizabeth II Centre was too small and not fit for purpose.
Johnson responded: ‘Well, if it’s too small, it’s your mum’s fault.’ Andrew stuck his tongue out.
Afterwards, Boris said: ‘I’m the last person to be a republican but, f**k, if I ever have to spend another lunch like that, I soon will be.’
The day Andrew and Harry came to blows
In January 2021 the Royal Family held a summit about Andrew at which it was agreed there was no way back for him because of the reputational damage he was causing the monarchy and his ‘ungracious and ungrateful’ attitude. Andrew’s relationship with his nephews was also a problem.
At a family gathering in 2013, Harry and Andrew had got into a heated argument, and punches were thrown over something Andrew said behind Harry’s back. According to a source close to both men, Harry told him he was a coward not to say it to his face.
Harry got the better of Andrew by all accounts, leaving him with a bloody nose before the fight was broken up.
At a family gathering in 2013, Harry and Andrew had got into a heated argument, and punches were thrown, according to Andrew Lownie
Later Andrew told Harry his marriage to Meghan Markle would not last more than a month and accused his nephew of going ‘bonkers’ and not doing any due diligence into her past. He openly accused Meghan of being an opportunist and thought she was too old for Harry, adding that his nephew was making the biggest mistake ever.
The source said: ‘Harry later told William he hated Andrew.’
According to the same source, the duke’s relationship with William is not much better. There have been tensions between the two men for years, partly occasioned by Andrew being rude about Kate. William refers to Andy as a ‘t****r’, perhaps not as bad as the vile names his brother Harry uses. Harry has referred to Andy as a ‘pooftah’, an ‘a***-h***’ and a ‘twit’.
William has long worked behind the scenes to evict his uncle from Royal Lodge, the home he occupies in Windsor Great Park. He thinks Andrew is abusing the property and his privilege there, the source says. ‘He also loathes Sarah, Andrew’s ex-wife, and can’t wait for the day when his father throws them both out. If Charles doesn’t, I guarantee you the first thing William does when he eventually becomes king is to get them evicted.’
Some 3,000 people were approached while researching Entitled
The book the Yorks tried to scupper
Many would have preferred the book from which these extracts are taken not to have been written, including the Yorks themselves.
I originally approached them with a view to letting them help shape the narrative by encouraging their friends and associates to talk to me – but they decided not to cooperate.
They told their contacts not to talk to me. The Foreign Office told ambassadors not to talk to me about Andrew’s time as special representative for trade and investment, even though he was a civil servant funded by the taxpayer. Legal letters were sent to my publishers, saying the duchess was monitoring my social media.
For years a curated narrative about the couple has been created, policed by armies of lawyers and PRs. The couple’s staff have been forced to sign non-disclosure agreements. The convention that parliamentary questions are not asked about members of the Royal Family has shielded them from any proper scrutiny.
Some 3,000 people were approached researching this book. Fewer than a tenth replied, but they included childhood friends, schoolmates, work colleagues, former staff (in spite of the NDAs), diplomats, charity workers, business associates, journalists who investigated the Yorks but were not allowed to publish their findings, friends and people who had encountered them in daily life.
From their contributions I have compiled Entitled: The Rise and Fall of the House of York. It is the story of how a popular couple fell from grace because of the flaws in their own characters and how they were allowed to leverage their privileged position as royals for personal gain with the connivance of the institution itself.
Adapted from Entitled by Andrew Lownie (William Collins, £22), to be published August 14. © Andrew Lownie 2025.
