Being a royal sibling is a surprisingly difficult role. As WorldViews has pointed out before, your position as "spare to the heir" is really just ceremony with no real clout, yet it leaves you very open to attacks from the notorious British tabloid press.

Many recent royal siblings seem to end up throwing caution to the wind and embracing their role as the black sheep of the family, be it Prince Harry's embrace of naked partying or Princess Margaret's often scandalous love life. But few have become as embroiled in controversy as Prince Andrew, the Duke of York and brother of Charles,  who has again been brought to international attention after being linked to an underage "sex slave" scandal.

The damning allegations, which claim that the Duke of York had intercourse with an underage girl procured by disgraced American investment banker Jeffrey Epstein, have led to not one but two denials from Buckingham Palace; a very unusual response which perhaps shows how seriously they are being taken.

This latest scandal can't have entirely come as a surprise, however. Not only have Andrew's links to Epstein been known (and speculated) about for years, but they fit into a broader caricature that Andrew has struggled to shift: That of "Randy Andy," the scandal-prone prince wooed by wealth and women.

Like Harry and Margaret, much of the attention on Andrew comes because of his love life. Andrew had married the red-haired Sarah Ferguson, nicknamed "Fergie," in 1986, but the couple separated soon after. Ferguson went on to cause controversy with her relationships with other men: In 1992, she was photographed topless in the south of France having her toes sucked by a Texas financial adviser, John Bryan. The couple divorced four years later.

Andrew, as evidenced by his nickname, was no saint either. The tabloid press had linked him to a variety of lovers before he married Ferguson, and after they separated it was no different. His romantic endeavors brought him some unlikely friends. "Prince Andrew turns up at my house at one in the morning and he wants to party," rock star Courtney Love recounted in 2006, explaining that they went on to drink tea together.

Despite their separation and divorce, Andrew and Ferguson remained surprisingly friendly (there were even rumors that they would eventually get remarried). And while that might seem like a nice thing, in the end it's ended up a problem for Andrew: In 2010, a tabloid newspaper reporter filmed Ferguson offering to sell access to the prince for £500,000 ($800,000). Ferguson's offer was apparently the result of her own substantial money problems.

There was no indication that Andrew knew of Ferguson's deal, but the news still resonated with a British public that had grown skeptical of the way that the prince appeared to mix business and pleasure. From 2001, Andrew had served as Britain's (unpaid) special representative for international trade and investment, but his suitability for the role was repeatedly questioned – not least for the huge expenses he claimed for the role (reported to be £620,000 he claimed in 2010, according to the Daily Telegraph) in addition to the £249,000 he receives annually for his royal duties. His fondness for fancy plane flights earned him another nickname – "Airmiles Andy."

Because of his position (or perhaps despite of it), Andrew also made some unlikely friends. There were reports of him meeting with Libyan dictator Muammar Qaddafi in 2008 or hosting the son of ousted Tunisian president Zine al-Abidine Ben Ali at Buckingham Palace. He was said to have met with the Ilham Aliyev, the president of Azerbaijan, on 12 separate occasions. His links with Kazakhstan have been a particular source of scrutiny – one Kazakh billionaire was found to have paid significantly higher than was listed for the prince's former home, for example.

Those with sympathy for Andrew will say he was simply doing his job, or at worst attempting to provide for his two daughters and their mother (a product of the British royals' shifting financial landscape). In the end, however, it was this "guilt by association" – in particular his relationship with Epstein – that led Andrew to step down from his role in 2011. Since then, he's taken on a far lower-key roles.

It's unclear what the consequences of the new accusations will be (the accusations haven't been tested in court and Buckingham Palace is said to be considering legal options), but the hit to his reputation may again prove dramatic. In the British press, many are treating it as a blow to not just Andrew but the entire royal institution.

"The Republicans are rubbing their hands in glee," Peter Oborne of the Telegraph writes.