The Biggest Troublemakers in the Royal Family, Revealed

It’s no secret that the British royal family is peppered with a few mischievous characters. And while Prince Harry’s partying days and Sarah Ferguson’s foot fiasco may be highlights, they are far from the only shenanigans to rock “The Firm.” In fact, many familiar royals have caused trouble over the years — over the centuries, too. Here’s a look at the biggest troublemakers in the royal family.

King Edward VIII

King Edward III

King Edward VIII gave up everything for his mistress. | Central Press/Stringer/Getty Images

There was a lot of scrutiny ahead of Prince Harry’s engagement to Meghan Markle since the American actress was previously married. This is because the crown previously did not approve of royals marrying divorcees. So you can imagine their shock when King Edward VIII gave up his place on the throne to marry his mistress Wallis Simpson — who had been married twice before. Needless to say, the family was in crisis.

Next: This former royal husband had trouble keeping it in his pants.

Captain Mark Phillips

Mark Phillips

Mark Phillips had plenty of mistresses. | POOL/Getty Images

Philips came into the royal family by marrying Princess Anne, and there’s was not a happy or romantic union. The well-known equestrian did however make plenty of time for romance with other women. His infidelity made headlines after news of a love child with a New Zealand art teacher became public. He and Anne weren’t together much longer after that, but Phillips continues to make headlines because of his scandalous behavior.

Next: This princess caused plenty of trouble up until her tragic death.

Diana, Princess of Wales

Princess Diana

Princess Diana was the ultimate troublemaker. | Eric Feferberg/AFP/Getty Images

Tradition-breaking princes William and Harry still have nothing on their late mother, Princess Diana. The People’s Princess made it her mission to break royal protocol, much to the chagrin of the rest of the royal family. She did all this while in the throws of a loveless marriage, of which she reportedly had a handful of affairs. One of the most infamous of which included a very disturbing recorded phone call with one of her lovers. Another was with a red-headed fellow that was rumored to be Prince Harry’s real father! (But we’ll get to Harry a little later.)

Next: The queen’s younger sister caused plenty of trouble in her heyday.

Princess Margaret

British Princess Margaret, Queen Elisabeth's sister

The queen denied Princess Maraget’s request to marry Peter Townsend. | STF/AFP/Getty Images

Queen Elizabeth II younger sister caused quite a stir when she asked for permission to marry Peter Townsend, who divorced his wife to propose to Margaret. The queen denied her sister’s request multiple times, before Margaret gave up on the drama all together. That is, until she married photographer Anthony Armstrong Jones with whom she publicly fought with — and supposedly cheated on — until they divorced in 1978.

Next: The known villain to anyone who is pro-Princess Diana.

Camilla, Duchess of Cornwall

Prince Charles and Camilla

Camilla is not very popular amongst the royal family. | BEN STANSALL/AFP/Getty Images

Yes, Camilla is the woman who got between Prince Charles and Princess Diana. But that isn’t the end of the Duchess of Cornwall’s run with the devil. Camilla is reportedly a big gossip, and was instrumental in trying to keep “unworthy” Kate Middleton from marrying Prince William. (She also reportedly told Prince Charles to instigate a breakup.)

Next: And if you think that duchess likes to cause trouble…

Sarah Ferguson, the former Duchess of York

Sarah Ferguson

Fergie is the black sheep of the royal family. | Jonathan Leibson/Stringer

Fergie got into plenty of trouble when she was Duchess of York, and she continued to draw the family’s ire even after she and Prince Andrew separated. She was busted for one of her (many) affairs when a photo was captured of her American lover sucking on her toes. Things got worse after she and Andrew separated, when she was caught accepting a cash bribe from a journalist wanting access to the royal family. Not surprisingly, most of the family has turned their back on her.

Next: At least she has support from her daughter… who is also a troublemaker?

Princess Beatrice

Princess Beatrice

Princess Beatrice is not a very popular member of the royal family. | DANIEL LEAL-OLIVAS/AFP/Getty Images

Standing by her scandal-riddled mother Sarah Ferguson is just one of the reason’s Princess Beatrice makes our list. The eldest daughter or Fergie and Prince Andrew is very vocal about her dislike of being in the shadows of other royals, despite being of royal blood. She is especially hostile towards Kate Middleton, with whom she has a long-standing feud with. (The Cheat Sheet breaks all that down here.)

Next: As it turns out, both of Beatrice’s parents have a pension for drama.

Prince Andrew, Duke of York

prince andrew

Prince Andrew is not popular for many reasons. | Alexander Hassenstein/Getty Images for IAAF

Queen Elizabeth’s second son has a whole laundry list of scandals in his wake. He has been linked to a slew of nefarious characters from across the world, and was caught in major trouble when he was connected to billionaire and convicted pedophile Jeffrey Epstein. The Duke of York has come under fire more recently for reportedly brokering huge deals with private foreign companies, and is regularly slammed for costing taxpayers for his around-the-world excursions.

Next: What about Andrew’s older brother, the heir apparent?

Prince Charles

Prince Charles of Wales

Prince Charles was no saint. | Carl Court/Getty Images

Yes, Diana was labeled the “troublemaker.” But her ex-husband was no saint either. The Prince of Wales had his fair share to do with his failed marriage to Diana, being regularly unfaithful. (Particularly with then mistress and current wife, Camilla.) But Prince Charles really embarrassed himself when he was caught on tape telling Camilla that he wanted to be reincarnated as her tampon. (An embarrassment that Princess Diana reportedly found very amusing.)

Next: Speaking of Diana, it’s time to take a look at her youngest son.

Prince Harry

Prince Harry sticking out tongue | Danny Lawson – WPA Pool/Getty Images

Harry’s tenure as a troublemaker dates back to his school days, when he reportedly got into trouble all the time. This behavior followed him into his 20s, when he channeled the grief of losing his mother into drinking and excessive partying. Notable shenanigans include playing strip poker in Las Vegas and dressing as a Nazi for Halloween. The red-headed prince appears to have cleaned up his act in recent years, however.

Next: The original instigator.

King Henry VIII

King Henry III

King Henry VIII had plenty of problems. | Hulton Archive/Handout/Getty Images

Ah yes, the original troublemaker. Henry VIII’s reign may be the butt of jokes now, but there was plenty of turmoil while he wore the crown. His difficulty producing a male heir and seeming spiral into madness drove him to make many rash decisions while on the thrown. Researchers have suggested that Henry carried a rare blood type that may have contributed to his fertility problems and growing paranoia.

Next: Mark Phillips wasn’t the only reason the marriage failed.

Anne, Princess Royal

Anne

Anne had a thing for a staff member. | CHRIS JACKSON/AFP/Getty Images

The Princess Royal is, arguably, nowhere near the troublemaker that ex-husband Mark Phillips is. She did, however, cause a bit of a stir following her divorce. No sooner was her union with Phillips over that Princess Anne got together with one of the royal staff members, naval officer Timothy Laurence. A newspaper obtained letters between Laurence and Anne from before her divorce from Phillips, which were reportedly “too hot to print.” Nevertheless, Anne and Laurence have been together ever since.

Next: One of the most fascinating instigators of hem all.

Anne Boleyn

Anne Boleyn

Anne Boleyn was quite the character. | Getty Images

There are numerous biographies and accounts on Anne Boleyn because she was, well, an incredibly fascinating woman. Most notably, she is noted for having a stronghold on King Henry VIII, and it’s believed that her way of getting into his head is what drove him to break religious ties with Rome and form the Church of England. Although, the extent to which she caused that much trouble is anyone’s guess.

Next: Troublemaker in training.

Prince George

Prince George of Cambridge eats a sweet as he leave following the service at St Mark's Church on Christmas Day on December 25, 2016 in Bucklebury, Berkshire. (Photo by Andrew Matthews - WPA Pool/Getty Images)

Little people can absolutely be troublemakers. | WPA Pool/Getty Images

Okay. So maybe Prince George is a little too young for this list. But there is no denying that he takes after his uncle, Prince Harry, when it comes to causing mischief. Prince William’s son is reportedly a bit of a rascal at school, and it only took him a couple weeks before he started begging his parents to let him stay home. Sounds like a regular royal troublemaker in training.

Next: Because Edward giving up the throne wasn’t bad enough …

Wallis Simpson, Duchess of Windsor

He gave up the throne for love. | Central Press/Getty Images

Simpson gained notoriety when her husband, formerly King Edward VIII, abdicated the throne to marry her. The two later became the Duke and Duchess of Windsor, but their brush with trouble was far from over. Simpson and her royal husband were alleged Nazi sympathizers, and it’s believed that Hitler was using the couple to gain information about the British royal family.

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