The Duke of York also hosted the son of the Tunisian dictator shortly before a popular uprising drove him from power — and the buildup of embarrassment has sparked calls that he be stripped of his role as special U.K. trade representative.
Buckingham Palace is in damage control mode as it attempts to keep the public's focus on the April 29 wedding between Prince William and tabloid favourite Kate Middleton, his university sweetheart.
British officials have rallied to Andrew's defence. The foreign secretary expressed his "confidence" in Andrew on Sunday, and a U.K. trade official voiced support for the prince to remain in the position, saying he does a "very valuable job."
But pressure is mounting and there is growing speculation over how long Andrew can hang on to his post.
Andrew has courted trouble before: His much-publicized divorce from Sarah Ferguson, her subsequent missteps, massive debt, a tell-all interview and a videotaped attempt to sell a U.K. tabloid access to Andrew stand in stark contrast to the glow surrounding William and Kate Middleton's courtship and upcoming nuptials.
Since becoming a special trade representative in 2001, Andrew has also drawn criticism for reportedly taking lavish trips in his role as an unpaid trade ambassador.
The latest revelations in the British media have centred on Andrew's friendship with convicted pedophile Jeffrey Epstein and claims that Andrew also had close ties to Seif al-Islam Gadhafi, one of the Libyan leader's sons.
Photos recently published in the British media show Andrew strolling in a park with Epstein — the New York billionaire jailed for soliciting underage prostitutes in Florida. Most recently, a photograph emerged showing Andrew with his arm around the waist of the teenage prostitute at the centre of that case.
While there has been no suggestion of any wrongdoing on the part of Andrew, the sum of events has prompted some soul-searching over whether the prince is a suitable representative for U.K. interests abroad.
"The duke recognizes that his association with Jeffrey Epstein was, in retrospect, unwise," a person familiar with the matter said, noting that it can be understood Andrew will not be photographed with Epstein again anytime soon.
But that's not placating some who say enough is enough. Last week, British lawmaker Chris Bryant claimed that Andrew had close links to Seif Gadhafi. Bryant called for Andrew to be fired, telling the House of Commons, "Isn't it time we dispensed with the services of the Duke of York?"
Buckingham Palace on Sunday rejected Bryant's claims, saying Andrew's interactions with the Gadhafi regime — and Tunisia's ousted dictatorship, too— fell within the mandate of his job as special trade representative.
"It was part of the British government's engagement with Libya at the time," a palace spokesman said on customary condition of anonymity.
The spokesman confirmed Andrew met Moammar Gadhafi twice. Both meetings were of public record and should not come as news, the spokesman said, adding that Andrew is "fully committed to his role as special representative."
"It is understood that he has the support of the government behind him," the spokesman said.
Government officials backed up that claim Sunday, citing Andrew's role in nurturing business interests.
"The Duke of York has made a valuable contribution to British business," a spokesman for government trade body UKTI said. "We continue to support him," he added, on customary condition of anonymity.
Foreign Secretary William Hague also expressing his full confidence in Andrew's work.
"I'm not an expert in ... the embarrassments," Hague told the BBC. "But certainly I've seen around the world a lot of good that he has done for this country."