Outrageous Tales From The Life Of Queen Elizabeth II's Son, Prince Andrew

Andrew Albert Christian Edward Windsor is a royal bad boy. Although rumored to be Queen Elizabeth II's favorite child, his controversial behavior has caused plenty of headaches for Buckingham Palace over the years. Like several other British royals, his life is a catalog of blemishes ranging from personal indiscretions to public scandals.

Born February 19, 1960, Prince Andrew is the queen’s second son and third child, behind brother Prince Charles and sister Princess Anne. He grew up to become a handsome hell-raiser. While he earned respect and admiration for his military service - he fought in the Falklands War in 1982 - he also earned a reputation as the “Playboy Prince” and “Randy Andy” who was always on the hunt for a good time.

In 1986, he seemed to settle down when he married Sarah Ferguson, daughter of a Scottish father and English mother, both of whom had some nobility in their lineage. The prince's mother even gifted him with a new title; he became Prince Andrew, Duke of York. Although the prince and his new wife genuinely seemed to love each other and the marriage produced two daughters, the couple divorced 10 years later.

Prince Andrew's exploits only heated up from there. The 2000s and 2010s were riddled with scandals for the Playboy Prince, especially as he cultivated questionable friendships and business relationships during his tenure as the UK's Special Representative for International Trade and Investment from 2001 to 2011. 

From naughty affairs to dealings with dubious characters - including convicted sex offender Jeffrey Epstein - Prince Andrew’s life is a collection of outrageous stories.

  • His Friend Jeffrey Epstein Was A Convicted Pedophile Who Ran A Sex Ring
    Photo: State of Florida / Wikimedia Commons / Public domain

    His Friend Jeffrey Epstein Was A Convicted Pedophile Who Ran A Sex Ring

    Many of Prince Andrew's friends have dubious reputations, including the late Jeffrey Epstein, an American billionaire who pleaded guilty in 2008 to prostitution charges. His Caribbean property, for example, was known as "Orgy Island," and he often "recruited" young girls and procured them for his adult friends.

    This apparently didn't persuade Andrew to end the friendship. In 2011, the two buddies chatted while they walked through New York's Central Park. His friendship with Epstein is one of many factors that led to Andrew's resignation as trade envoy.

    Months after Epstein allegedly took his own life in prison in August 2019, Andrew released a statement that he would "step back from [his] public duties" as a royal. He announced the decision on November 20 of that year, following a controversial interview in which he candidly discussed his relationship with Epstein.

    It has become clear to me over the last few days that the circumstances relating to my former association with Jeffrey Epstein has become a major disruption to my family’s work and the valuable work going on in the many organizations and charities that I am proud to support… Therefore, I have asked Her Majesty if I may step back from public duties for the foreseeable future, and she has given her permission.

  • He Was Accused Of Having Relations With A 17-Year-Old 'Sex Slave'
    Video: YouTube

    He Was Accused Of Having Relations With A 17-Year-Old 'Sex Slave'

    Prince Andrew's relationship with Jeffrey Epstein also inevitably made him vulnerable to accusations about sexual misconduct. In 2015, Virginia Roberts, an American, alleged that she had been Epstein's "sex slave," and was forced to have sex with Andrew. 

    Worse, Roberts was only 17 at the time of the alleged rape. Her allegations were damning for the royal, as she detailed her various sexual encounters with the prince, including an orgy in the Caribbean

    Andrew strongly denied the allegations, and a judge eventually threw them out.

  • One Of His Close Friends Is A Libyan Gun-Smuggler

    One of the most ill-advised connections in Prince Andrew's network is his friendship with Tarek Kaituni, a convicted gun smuggler. But Kaituni's business didn't seem to bother the prince all that much. In 2008, Kaituni even paid for Prince Andrew to enjoy a vacation in Tunisia. The uproar over the trip didn't seem to deter Prince Andrew, either.

    Only a few years later, the British press again scrutinized the prince's relationship with a convicted gun-smuggler when Kaituni was a guest at Prince Andrew's older daughter's private birthday party in 2011. At least he was a considerate guest: Kaituni reportedly presented Princess Beatrice, the birthday girl, with a diamond necklace.

  • 'Air Miles Andy' Takes Choppers Everywhere - Even Out To Lunch

    With responsibilities ranging from royal engagements to business meetings connected with his position as trade envoy from 2001 and 2011, Prince Andrew is a very frequent flyer. But, as someone born into extreme wealth and privilege, he doesn't always travel like everybody else. 

    The British press bestowed him with the nickname "Air Miles Andy," as the royal apparently travels so frequently by air. And he often opts to hop into helicopters rather than taking a car or train for relatively short travels, thus costing British taxpayers hundreds of thousands of pounds. In one particularly blatant instance in June 2003, Andrew took a privately chartered chopper to attend a business lunch only about 60 miles away.

  • 'Randy Andy' Is Alleged To Have Some Bedroom Quirks

    "Randy Andy," as he is sometimes known, reportedly had a string of affairs. Indeed, he once supposedly quipped, "My only vice is women." Not only that, but he appears to harbor some quirky bedroom behaviors. 

    A former Playboy model, Denise Martell, alleged that Prince Andrew invited her to tuck him into bed. The prince also apparently likes to joke around by donning his girlfriend's underwear and strutting across the bedroom in it.

  • He Wanted To Marry His Actress Girlfriend, But Her Racy Film Career Made That Impossible

    Prince Andrew had a reputation as the "Playboy Prince." However, by many accounts, one of his most serious girlfriends before he married Sarah Ferguson in 1986 was Kathleen “Koo” Stark. She was well-liked by many members of the prince's family - including the queen herself - but Stark's career was not unblemished by royal standards. 

    Being an American actress was not necessarily a bad thing - witness Prince Harry's relationship with Meghan Markle. The problem was that at least one of Stark's films had been quite racy, especially because she appeared nude in it. The fact that she had appeared in a movie that was essentially soft porn made marriage between Stark and Prince Andrew virtually impossible, so they parted ways as friends.