PRINCE Andrew had three meetings with brutal Libyan dictator Colonel Gaddafi and enjoyed a long-term friendship with a convicted gun smuggler.
The Duke of York‘s bizarre ties to the North African country would eventually bring his prized role as UK trade envoy crashing down around his royal ears.
His links to the former Gaddafi regime have come under further scrutiny in the wake of the mystery over Andrew’s money.
Royal finances expert David McClure has said Andrew’s private wealth remains “shrouded in mystery”, 15 to 20 years after questions were first raised about his lifestyle.
Meanwhile, former Lib Dem MP Norman Baker said: “Andrew has accumulated a lot of money over the years that we don’t know about.”
He went on: “He has clearly been getting money from elsewhere for decades.”
David also pointed out Andrew is alleged to have worked as a “door opener” for foreign banks in a number of countries around the world for years.
Andrew’s links to Libya date back around 20 years, when the Duke visited an arms fair in Jordan with his new Equerry Robert Olney.
A number of countries including Libya came to buy weapons from the British Army and British arms companies.
In 2005, Andrew was first introduced to Libyan gun smuggler Tarek Kaituni, formerly married to glamorous Dutch supermodel Lisa van Goinga, by an unnamed Middle Eastern sheikh.
Kaituni, who has US citizenship, would later brag of his influence over the Duke of York, and helped set up secret meetings with Libyan dictator, Colonel Muammar Gaddafi.
In 2005, the same year Andrew met Kaituni, the prince’s new pal was convicted of smuggling a sub-machinegun into France.
Kaituni spent several years on remand in a Paris jail for smuggling the gun before he was given a two-month suspended sentence, and fined 10,000 Euros a year later.
He has since claimed, somewhat bizarrely, that he was never convicted, and that the crimes were committed by another man who shares his name.
None of this seemed to bother Andrew, who enjoyed a four-day holiday in Tunisia with Kaituni in November 2008, shortly before visiting Colonel Gaddafi in Tripoli.
Before Andrew lost his trade role, Kaituni was invited to Princess Beatrice‘s 21st birthday party in Spain in August 2009, where he also gave her a diamond pendant worth £18,000.
He is pictured at the party with Kaituni and a bevvy of glamorous women.
And Andrew’s ties to Libya go even deeper. In July 2007, he attended a lavish party thrown by an unnamed Libyan businessman in the French resort of Saint Tropez, where he was snapped dancing wildly with US socialite Chris Von Aspen.
A year later, in July 2008, he was pictured dancing with Libyan model Nadia Boejna at another party in Saint Tropez, this one thrown by French wine tycoon Claude Ott.
The first known time Andrew visited Libya was in November 2007, where he waited three days for a meeting with Colonel Gaddafi, but faced an embarrassing snub.
However, he did get to meet the oil-rich country’s prime minister, as well as business leaders, politicians and – most importantly – the President’s son Saif Gaddafi.
“Air Miles Andy” as he was known racked up a cost to the taxpayer of more than £50k in the course of his two-week visit to North Africa, including £32,600 on flights and £20,000 on hotels.
Finally, in the summer of 2008, Andrew was granted an audience with the brutal dictator, when he made an unscheduled trip to Tunisia as a guest of the Tunisian despot’s son-in-law Sakher El Materi.
The “notoriously corrupt” Materi’s father-in-law, President Zine Ben Ali, was overthrown in a coup in January 2011.
Materi fled Tunisia for the Seychelles following the revolution and was later convicted of corruption in absentia by a court in his home country.
In June 2011 he was first sentenced – along with his wife Leila – to 35 years in prison for embezzlement and misuse of state funds.
Weeks later he was convicted of possessing illegal drugs and weapons and given 15 years in jail.
In June 2012 he was given a life sentence in absentia by a military court over the killing of protesters during the revolution.
At Materi’s home, the Queen’s favourite son attended a gala dinner in honour of Gaddafi, who was on an official visit.
Reports say Andrew greeted the dictator warmly, and the pair spoke for more than 15 minutes.
Three months later, Andrew found himself back in Libya, where this time, he made a private visit to see Gaddafi.
He would return in early 2009, staying in Tripoli’s five-star Corinthia Bab Africa Hotel.
A Buckingham Palace spokesperson said at the time: “[Andrew] has only met Colonel Gaddafi officially once, but there may have been private occasions because it is the Duke’s job to develop long-term relations with key individuals.
“But it is always for the betterment of British interests, that’s the only reason he is doing it. He works extremely hard, at the behest of the Foreign and Commonwealth Office, on behalf of UK companies.”
HOAR Online has approached Sakher El Materi and Tarek Kaituni for comment.
Andrew’s association with the Gaddafi family allegedly saw him “court” the dictator’s favourite son Saif al-Islam, according to The List.
The Duke hosted Gaddafi’s son at a reception at Buckingham Palace. Saif would later face charges of crimes against humanity in the aftermath of Gaddafi’s overthrowal in a bloody coup in 2011.
That same year, pressure over Andrew’s various ties to dictators around the world would see his role as UK trade envoy brought to an end.
Calling for the Duke to lose his role, Labour MP Chris Bryant told the House of Commons: “Isn’t it especially difficult to explain the behaviour of the special ambassador for trade who is not only a close friend of Saif Gaddafi but is also a close friend of a convicted Libyan gun smuggler, Tarek Kaituni.”
But despite the disgrace, Andrew continued his association with Kaituni, now 58, and even invited him to Princess Eugenie‘s wedding to Jack Brooksbank.
In October 2018, he attended both the private ceremony at St George’s Chapel in Windsor as well as the later black-tie reception.
For his part, Kaituni boasted of his influence over the Duke of York and told undercover reporters he had played a key role in securing the release of Libyan Lockerbie bomber Abdelbaset al-Megrahi in August 2009.
Buckingham Palace has always played down Andrew’s friendship with Kaituni – who also spent a year in prison in Tunisia for drug possession – describing him as simply a contact.
HOAR Online has approached a spokesperson for Prince Andrew for comment.