Prince Andrew, Duke of York, attends the Sunday Service at the Royal Chapel of All Saints, Windsor. Photo / Getty Images

Opinion:

You can say this for Prince Andrew: The man is peerless when it comes to generating PR messes.

For more than six months now, the defrocked royal has been mired in a civil sex abuse case after Virginia Guiffre accused him of sexually assaulting her on three occasions. (He has always vehemently denied her claims.)

Sure, that sorry chapter might have drawn to a close this week after he agreed to settle with Ms Guiffre, paying her a reported $22.7 million (money that is said to be coming from his mother the Queen's bank account) but over the last 40 years, Andrew has managed to clock up what must be a record number of controversies and mucky imbroglios.

For years in the '80s and '90s it was his older brother Prince Charles' crumbling marriage and infidelity which might have looked like the biggest blot on the monarchy's image but take a walk down memory lane and Andrew is the clear frontrunner in the scandal stakes.

Ready to get a bit grubby?

A 't*ts and bums man'

Rewind to his early 20s and Andrew was facing the quandary that every royal spare has had to contend with since the Norman invasion: What to do with oneself given his brother was in excellent health? Andrew's answer seemed straightforward enough: Chase women with glee abandon and fly helicopters, both of which he managed to do with gusto.

It was not long before the Queen's second son was working his way through what Alan Rusbridger, later the editor of The Guardian, dubbed his "gallery of crumpet" dating a series of models and actors including most notably Koo Stark.

Then there was the war stuff with the naval officer taking on frontline duties during the Falklands War. At the time, Andrew Morton nauseatingly wrote of him, "His arrival on the scene has given a new meaning to the initials HRH. With Andrew, they stand for His Royal Heart-throb."

But that penchant for women would see him later, in the wake of his divorce from wife Sarah, Duchess of York, be associated with scores of names including a Playboy model and a five-year association with a Sports Illustrated model, none of whom were likely contenders to be the new Duchess of York.

In 2015, one associate of his told The Times: "He has always been a t*ts and bums man."

"I've witnessed a few unbelievable comments. He made some completely inappropriate comment to someone who was pregnant and had massive boobs.

"You just think, 'Oh, yikes' – schoolboy stuff. And he would roar with laughter and think it was hilarious, while said victim looked ashen-faced. So I can see why he got caught up in this. It is all good humour for him."

His mother must be so proud.

Dinner with an autocrat

In 2001, after retiring from the navy, Andrew replaced the Duke of Kent as the UK Trade Investment (UKTI) special envoy. It should have been a very straightforward, if dull, gig.

Should have, that is.

In May 2008, Andrew travelled to the Egyptian resort of Sharm-el-Sheik for the World Economic Forum (WEF) where he eyebrow-raisingly dined with then Kazakhstan's autocratic president Nursultan Nazarbayev. (He held the reins of power from 1991 to 2019.) Depending on which source you turn to, some news outlets have called Mr Nazarbayev a dictator.

According to The New York Times, Mr Nazarbayev's "family enjoyed vast riches, with influence in the banking and extraction industries and real estate in Switzerland, London and New York".

Between 1998 and 2020, members of the country's ruling elite bought more than $1 billion worth of property, according to London think tank Chatham House.

Keep Mr Nazarbayev in mind it's a name you are going to hear again.

Holidaying with a criminal

Many, many of Andrew's messes come down to the people he associates with and by 'associates' I mean holidays, dines and pals around with.

Take in November of 2008 when it emerged that he had just been on a four-day getaway in Tunisia in which he, the Times reported, " accepted hospitality from a convicted gun smuggler".

Andrew is said to have stayed in luxurious hotels and been travelling with Libyan-born Tarek Kaituni who was convicted several years earlier for buying a machine gun and smuggling it into France.

Kaituni, during the trip, was "seen paying bills for the group at two hotels," per reporting from the time. (A spokesperson for the royal said he would be reimbursing Kaituni for the expenses.)

The Lockerbie bomber connection

Immediately following that holiday with Kaituni, the duo travelled to Libya where the Duke reportedly dined with the country's dictator Muammar Gaddafi, who had personally ordered the 1988 Lockberbie bombing which killed 270 people.

(That jaunt was reportedly the second time in three months that the Duke had travelled to Northern Africa to meet with Kaituni and Gadaffi.)

Mr Rowland was also part of one of the trips to visit Gaddafi, the Daily Mail has reported.

One year after the royal met the bloodthirsty autocrat, the man behind the bombing, Abdelsbaset al-Megrahial-Megrahi was released from prison and the UK picked up a lucrative oil deal in the region.

The topless women photo and the Crazy Girls

While it was his then-wife Fergie who was caught topless sunbathing in 1992, it was his turn a decade or so later when in 2001 he was photographed on a boat in Thailand surrounded by a gaggle of lithe, topless women.

During the trip to Phuket with Epstein, the royal stayed in a $7500-a-night private villa, The Sun has reported with the duo reportedly visiting nearby Patong's red light district.

Per the Sunday Mirror, the duo visited an adult bar called Crazy Girls by Rock Hard.

"I was amazed to see the Prince here," the manager told the paper.

"But he was not at all fazed and seemed quite relaxed until people realised who he was."

When the manager asked him, "Are you Prince Andrew?" he is said to have replied: "Yes I am. How did you know that?"

Well, no one has ever accused the man of being a Mensa candidate.

Beatrice's $37,000 necklace

Remember gunrunner Tarek Kaituni who Andrew holidayed with? Well, it was later reported that Kaituni had controversially given Andrew's daughter Princess Beatrice a $37,000 diamond necklace for her 18th birthday and was a guest at celebrations to mark her big day at a private villa near Marbella.

Kaituni has remained in Andrew's inner circle and was later invited to his other daughter, Princess Eugenie's, 2018 wedding.

The $28M travel bill

Andrew's ten-year stint as a trade envoy wasn't just controversial because of who he hung out with but how much money he spent supposedly doing his bit for Blighty.

In 2011, the same year he stepped down from the cushy job after a photo emerged of him with convicted sex offender Jeffrey Epsetein, it was revealed that his decade of travel on behalf of UK trade had, according to The Telegraph, cost taxpayers more than $28 million in travel and security expenses.

His taste for first-class flights and five-star hotels saw him spend more than $36,000 on a three-day trip to Switzerland and $63,700 on an 11-day trip to the Middle East.

That year, the Guardian reported that "The expense of funding the Duke's role as trade ambassador comes amid growing concern that he is blurring the line between his official trips abroad and his personal business."

The crumbling mansion and the $5.6m cheque

In 1986, when Andrew married Fergie, the Queen gave them the land and money to build their dream home, Sunninghill Park. Less than 20 years later, it would sit empty and crumbling in the wake of their divorce after Andrew moved into the 31-room Royal Lodge after the Queen Mother died in 2002.

Sunninghill Park was a colossal and very costly white elephant of a property that Andrew struggled to offload.

In 2004, "the Duke used an official trip to Saudi Arabia and Bahrain … to try to find a buyer" for the monstrosity, the Telegraph later reported.

Then in 2007, after five years on the market, the royal finally found someone willing to take it off his hands, namely Timur Kulibayev, a Kazakh billionaire.

Not only was Mr Kulibayev, the son-in-law of Kazakhstan's autocratic president Nursultan Nazarbayev, willing to buy the badly dilapidated property, he was willing to pay $5.6 million over the asking price.

Why? Well, that has never been answered with questions still swirling to this day about how Andrew has afforded his luxe lifestyle when he technically lives on a fixed stipend from his mother.

Cash-for-access

Oh Fergie … we were always going to get to you. In 2010, the Duchess managed to blow her own toe-sucking escapades out of the scandalous water after she was secretly filmed offering to sell access to trade ambassador Andrew for $943,000 (£500,000).

In an encounter with an undercover reporter in New York, she allegedly said: "What I want you to do next is to meet Andrew … as soon as you come to London, come to the Royal Lodge. I'll introduce you and sit down and you'll talk to him about whatever."

Later, she was filmed in London saying "£500,000 when you can, to me … open doors" and accepting a $55,000 cash payment. She also said: "Look after me and he'll look after you."

"I did ask Andrew about meeting you … I never talk about money ever, but since we've got business hats on I'm going to …"

The Duke of York vigorously denied any knowledge of his ex-wife's manoeuvrings.

Interestingly, one of Fergie's friends, a clairvoyant named Azra Scagliarini was soon named as having been the intermediary who set up the fateful meeting.

At the time, Andrew said he had "never heard of" Ms Scagliarini only for the News of the World to later publish a handwritten note from 1999 in which the royal thanked her for her "help and friendship" which was "much valued".

At that stage, a spokesperson for Andrew clarified things saying, "He has not met Azra Scagliarini and she is not a friend of his. The Duke takes very seriously any suggestion that he has lied in his matter."

Hang on, there's another dictator in the mix

Another year, another oppressive regime for Andrew to cosy up to!

In 2014, it was revealed that Andrew was about to head off to Azerbaijan for talks with the country's billionaire despotic leader President Ilham Aliyev, despite the fact that he was no longer a trade envoy of any sort.

Turns out the trip was the 12th meeting between the Duke and Mr Aliyev, whose regime has been accused of rigging elections and of torturing political opponents.

(Andrew has also undertaken meetings with the King of Bahrain and the Yemeni president, both countries with abysmal human rights records. )

The $2.8M mystery loan

In November last year it was revealed that Tory David Rowland had paid off a $2.8 million loan which Andrew had taken out from Banque Havilland, which Mr Rowland's family controls.

According to the Times, Andrew opened an account with the private establishment in 2015 and then proceeded to borrow an eye watering $236,000 every three months for the next two years and on ten occasions.

In November 2017, he upped his request, asking for $472,000 for "general working capital and living expenses". (Just how many fascinators was he buying for his daughters?)

In December 2017, the full debt was paid off by a company registered in the tax haven of Guernsey and which was controlled by the Rowland family.

That's not all. It had previously come out that Mr Rowland had paid previously $75,000 to help clear Fergies debts at one point when she was sailing close to bankruptcy.

Andrew, while still a trade ambassador, had opened the Luxembourg outpost of the Banque Havilland in 2009 and then in 2012 in Monaco.

Daniela Elser is a royal expert and a writer with more than 15 years experience working with a number of Australia's leading media titles.