Shocking Facts About Prince George, The Royal Rebel

May 31, 2021 | Byron Fast

Shocking Facts About Prince George, The Royal Rebel

Prince George, Duke of Kent was so bent on challenging royal tradition that he usually took it a step too far. He was an unabashed partier and a shameless bedroom romper. He fearlessly stomped the streets in drag and pursued illicit affairs. George's story is fun and tragic in equal measure, and the scandal surrounding him is astronomical...

...So why has he been largely forgotten?

1. He'd Never Wear The Crown

On December 20, 1902, Prince George, Duke of Kent joined Britain's royal family. With his father and three brothers ahead of him, he was fifth in line for the throne. It was pretty obvious that, unless there was some terrible disaster, he'd never be King. Growing up without this pressure afforded the young Prince greater freedom to push the boundaries and test his limits.

It was exactly this freedom that led him down a path of debauchery.

Prince George, Duke Of Kent FactsWikimedia Commons

2. He Was The Favorite

Even though he had four brothers and a sister, George stood out among the crowd. His doting parents considered him to be the most intelligent and talented of all their children, and they never failed to shower him with love. His childhood was a charmed one. He wanted for nothing. But this wasn't enough for George. As he grew older, he became bored of how easy it all was. He wanted something more.

Prince George, Duke Of Kent FactsGetty Images

3. He Followed In Their Footsteps

Needless to say, life as a royal boasted an unholy amount of tradition. Because of this, George spent much of his early life trailing the footsteps of his older brothers. This meant the typical uptight prep schools and even a long stint at the naval academy. But George was never cut out for a life at sea, and whenever he was on a boat, he suffered greatly.

Prince George, Duke Of Kent FactsGetty Images

4. He Suffered At Sea

George spent a good part of his young life in the Royal Navy even though he despised every second of it. Determined to prove his worth and backbone, he stuck it out. But what was it that made him unhappy about being at sea? Was it being away from family? Was it the relentless boredom? Certainly not. George suffered from sea sickness.

He couldn't wait to leave the sea behind him. After all, the lively nightlife in the city seemed far more appealing than the navy's nauseating duties.

Horatio Nelson factsGetty Images

5. He Tested The Waters

When George finally finished with the dreaded Navy, he decided to break away and forge his own path. For the first time, he dipped his toes into unroyal waters and tested them. He wanted to do something nobody else in his family had ever done before. And so, in a shocking move, he found himself a job. But this wasn't just any job. George was the first royal to ever take a job as a civil servant.

Prince George, Duke Of Kent FactsWikimedia Commons

6. He Was A Hipster

While he worked at his rebellious job at the Foreign Office, George began to wonder what extravagances London had to offer. He found that his older brother, Edward, had already made a name for himself in the party circuit and George wasted no time joining these fashionable circles. The two of them became best friends and the talk of the town. They were magnets for gossip, but it wasn't alway pretty.

Prince George, Duke Of Kent FactsGetty Images

7. He Was Part Of The In Crowd

George and his brother Edward soon joined an elite 1920s group. They earned the moniker “Bright Young Things” and the media labeled them as bohemians, aristocrats, and socialites. This outlandish collection of partiers became famous for fancy dress events. At night, they even organized showy treasure hunts throughout London. However, it wasn't all fun and games. These Bright Young Things had a dark side.

Prince George, Duke Of Kent FactsGetty Images

8. He Partied Hard

George and his big brother thoroughly enjoyed the wild liberation that came with joining the Bright Young Things. After all, another aspect of this hearty partying group was indulgence. Mostly it was drinking, but there was also some pretty heavy drug use. The hijinks of the Bright Young Things was the inspiration for the Evelyn Waugh book, Vile Bodies. I guess the title says it all.

Johnny Carson factsPixabay

9. His Older Brother Was A Famous Quitter

Once George’s older brother, Edward, finished sowing his wild oats, he had no choice but to settle down and take on the duller role of King. But Edward didn’t last as the Monarch. Running wild and free with his brother George had had a lasting effect. In the end, Edward VIII abdicated the throne to stay with the woman he loved—American divorcée Wallis Simpson. Like his brother, George kept one eye on the ladies, getting himself into just as much trouble.

Wallis Simpson FactsGetty Images

10. He Dated A Triple Threat

According to rumor, George's first known affair was with singer, dancer, actor—Jessie Matthews—whose dalliances always seemed to dominate the spotlight. I would never say she was a bad seed, but a judge certainly did. After reading some of Matthews’ personal letters, the judge declared that she was “odious"—certainly an unsuitable match for a Prince.

Just like Matthews, George also wrote love letters—the contents of which often came back to bite him from behind.

Prince George, Duke Of Kent FactsFlickr

11. He Was Bi

George's romantic attachments were not only with women—they were with men too. One man he had an affair with was Cecil Roberts, who claimed to have dated Laurence Olivier. George also had a fling with the multi-talented and flamboyant character, Noël Coward. Together, these two rebels found plenty of time to dig themselves into delicious trouble.

Prince George, Duke Of Kent FactsWikimedia Commons

12. He Was Fearless

As one story goes, officers took George and Coward into custody for allegedly working as escorts. But once the officers realized they’d captured a Prince, they quickly let them go. Back then, the press was far more reserved. Even though George's bisexuality was common knowledge, the media refused to print anything that might cast a shadow on their darling royals.

With both the police and the press in his corner, George had little to fear.

Airport X-Ray FactsShutterstock

13. He Loved Dressing Up

On one occasion, while visiting the theater, George ended up wandering around backstage. That's when he stumbled across the actress Gertrude Lawrence's dressing room—a treasure trove of exciting accessories. When Lawrence finished her performance and returned to her dressing room, she found George rifling through her belongings.

More specifically: he was trying on Lawrence’s wigs. His delight in wearing them awoke a new fascination. This was only the beginning.

Prince George, Duke Of Kent FactsFlickr

14. He Wore Drag

Trying on wigs backstage ignited a spark in George. Some time later, British Security Services were suspicious when they saw a pair of elegantly dressed ladies running down a West End street. When they went to investigate, they were shocked to learn that the ladies were actually George and Coward dressed in full drag. George was clearly having the time of his life, but that was before he met Kiki Preston.

Prince George, Duke Of Kent FactsPixnio

15. He Met An Enabler

While George’s little escapades seemed harmless enough, when he met American socialite Kiki Preston—a cousin to the Vanderbilts—things took a much darker turn. Preston's sinister nickname said it all: “the girl with the silver syringe." It wasn't long before she introduced George to morphine, and soon, it became his drug of choice. But it wasn’t just the drugs that attracted George to Preston. She was her own kind of addiction.

Prince George, Duke Of Kent FactsGetty Images

16. He Had Threesomes

Kiki Preston was an out of control partier who used both drugs and men freely, and George quickly became her eager accomplice. Rumor has it, the two of them once shared a bed with Jorge Ferrara—the Argentine ambassador’s son. George’s antics had moved into a new realm: international threesomes. Someone had to stop him. But who was up to the challenge?

Elizabeth Chudleigh FactsShutterstock

17. He Didn't Want To Give Her Up

Brother Edward saw what was happening to George and immediately pinpointed the root of his problems—Kiki Preston and her silver syringes. Desperate to save George from her clutches, he begged his brother to give Preston up, but George wasn’t budging. Morphine and Kiki were all he wanted. His refusal to comply forced Edward's hand: things were about to get nasty.

Edward VIII factsWikipedia

18. His Girlfriend Got The Royal Heave Ho

Edward was determined to rescue his brother from Kiki Preston and certainly had the political clout to do it. And so, Edward devised a plot to separate George and Preston forever: he used his royal super powers to get her kicked out of England. But with one threat gone, another remained. George's drug habit was worse than ever.

Clara Bow factsPixabay

19. He Did A Stint In Rehab

Having rested George from Preston's evil claws, Edward faced a new challenge—getting George clean. Betty Ford Clinics were still about 50 years away, so Edward found the next best thing: a secluded country retreat. Here, Edward locked George up and forced him to endure a harrowing rehabilitation program. It was painful, yes—but did it work?

Prince George, Duke Of Kent FactsGetty Images

20. He Reunited With Trouble

A few years later, George had another brush with temptation. While holidaying at the seaside in Cannes, he bumped into his old flame, Kiki Preston. The connection was instantly electric. Whether George wanted her, her drugs, or both is anyone’s guess. With these two pleasure-seekers reunited, trouble crested the horizon. It was about to get physical.

Prince George, Duke Of Kent FactsGetty Images

21. He Dodged A Bullet

When George reunited with Kiki Preston on the beach in the south of France, it must have felt like the good old days—they were still wildly attracted to one another. But Preston was dangerous. With her around, George was bound to relapse. Once again, George had to be physically ripped away from her. Having dodged one bullet, George took his risky business elsewhere.

Halle Berry FactsShutterstock

22. He Got Involved With A Dangerous Crowd

George often pursued talented, but also very intelligent, people. In fact, he found himself romantically involved with Anthony Blunt, one of Cambridge’s brightest minds. Blunt was a member of the Cambridge Apostles: a secret discussion group of 12 undergraduates. Sounds harmless enough right? A bunch of bookworms having a chat? Well, don’t count on it.

Everything George gravitated toward was far from innocent.

Prince George, Duke Of Kent FactsWikimedia Commons

23. His Boyfriend Was A Spy

While the Cambridge Apostles may sound like—let’s be honest—a really boring book club, they were anything but. This group recruited George’s boyfriend, Anthony Blunt, to be a spy for the Soviet Union, and Blunt went on to recruit others for the same nefarious purpose. Unfortunately for George, this was no place for a royal.

While a traditional royal lifestyle was far from the life he desired, the Prince had no choice but to answer the call of duty.

Virginia Hall FactsShutterstock

24. He Kept It Pure

In order to preserve the royal bloodline, it was common for royals to marry their own cousins. And this is exactly what George did—he wed his first cousin, Princess Marina of Greece and Denmark. In 1934, the two tied the knot in a spectacular ceremony at Westminster Abbey. But behind closed doors, the true nature of their union remained a mystery.

George certainly liked his bride and said as much, but his few comments about her were rather peculiar.

Prince George, Duke Of Kent FactsWikipedia

25. He Still Itched For Freedom

After settling into married life, George had a few good things to say about his new bride. Firstly, he especially liked that she craved independence. Coincidentally, he also craved independence and now had every reason to do as he pleased. Secondly, he liked that she didn’t complain about his fast driving. In George's books, these were win-wins: the more freedoms he could still enjoy, the better.

Prince George, Duke Of Kent FactsWikimedia Commons

26. He Slayed London Society

George and his wife took London society by storm and they successfully enamored the press with their glamor. The couple brought together the brightest of the bright, which mostly included forward thinkers and artists. As such, their lavish parties changed the way people perceived the Royal Family. But nothing was as it seemed—something ominous lurked beneath the glittering hubbub.

Prince George, Duke Of Kent FactsGetty Images

27. He Hid His Private Life

The average British citizen only knew George’s public persona: that he was a handsome and brave hero who married a beautiful and elegant woman. In those days, the public wasn't made aware of celebrities' private lives. There weren’t paparazzi hiding behind trees or journalists rummaging through garbage cans. For George, this was a blessing: his true inclinations were almost completely hidden.

Prince George, Duke Of Kent FactsGetty Images

28. He Dated A Notorious Lover

Even though George was a married man, he still continued to have romantic affairs. His next triumph was the notorious Margaret Campbell, the Duchess of Argyll. Campbell later became famous for an accusation made against her that, while married, she consorted with 88 other men—and there were photographs to prove it. I guess you could call George a drop in the bucket.

Prince George, Duke Of Kent FactsGetty Images


29. He Wrote Dirty Letters

George was a prolific writer but instead of novels or poems, he mostly wrote private love letters to his many girlfriends and boyfriends. Pouring his heart and soul onto paper transformed these notes into precious goods. Although George tried his best to keep these lascivious letters hidden from the public, he could never have foreseen how valuable they were to complete strangers.

Queen Barbara of Poland FactsShutterstock

30. He Never Forgot Him

Even after all this time, George still wrote love letters to Noël Coward. We can assume George trusted Coward never to share these racy letters with anyone, but there was one thing he could never have anticipated—the threat of thieves. On one occasion, there was a breaking and entering at Coward’s home and among the items taken were George’s naughty letters. But this wasn’t the only way that George’s letters got out.

Prince George, Duke Of Kent FactsFlickr

31. He Wasn't Discrete

George’s correspondence wasn’t just for friends and lovers. He even wrote to the people he paid to be intimate with. A certain male escort kept George’s mail and put it to good use: he blackmailed him with it. As a result, George had no choice but to shell out a pretty penny for the letters he’d thoughtlessly penned. With power and status on his side, the Prince was far from phased. After all, he still had the press on his side.

Mary Shelley FactsShutterstock

32. He Had Friends In High Places

You’d think that, considering George’s lewd letters and erratic behavior, the press would’ve had a field day with his scandalous antics. But journalism was different back then: media members were die-hard royalists and absolutely loyal to the crown. Friends, like newspaper publisher Lord Beaverbrook, ensured that the royal family’s misdeeds never appeared in print. George knew this and didn’t seem to care what people saw him do—or who he did it with.

Prince George, Duke Of Kent FactsWikimedia Commons

33. He Fraternized With The Enemy

George and his wife’s lavish parties had an ominous undercurrent. During this time, he befriended a questionable character—Stephanie Von Hohenlohe. She was not only intimate with George’s family, but also with Germany’s threatening Führer. With the powerful Third Reich gaining power, George’s dealings with Hohenlohe were dangerous. With no regard for the consequences, the Prince headed down a perilous path.

Prince George, Duke Of Kent FactsGetty Images

34. He Was Political

Some historians believe that Prince George played an important role in planning a coup. According to them, George worked with a man named Rudolf Hess—a deputy to the German Führer. But what were they actually trying to accomplish? And who was the coup intended for? Turns out, the target was none other than Prime Minister Winston Churchill. The plan was beyond diabolical.

Hitler And Hess.Getty Images

35. He Almost Destroyed Europe

Some historians believe that George and Hess were trying to remove Churchill from power. But that wasn’t all. If they were successful in taking down the Prime Minister, their next step was to forge a treaty with the Führer of the Third Reich. Pretty heavy stuff for a royal best known as a fun-loving scoundrel. On the flip-side, another possibility presented itself—one that cast the Prince in a more positive light.

Pamela HarrimanWikipedia

36. He May Have Been A Hero

Instead of trying to start a coup, some historians believe that George was working as a sort of go-between. They believe that Prince George tried to prevent WWII by using his German connections: perhaps he attempted to negotiate directly with the Führer. But what actually happened? Unfortunately, due to a tragic turn of events, his true dealings with the Fuhrer remain a mystery to this day.

Evil People Who Made History QuizFlickr, Recuerdos de Pandora

37. He Boarded An Ominous Flight

By the time WWII began, it appeared that George had finally stopped fooling around and had started taking his royal duties seriously. He even joined the Royal Air Force and tried to make a difference. One of his key roles was to boost the morale of the enlisted men. That’s why, in August 1942, George boarded a flight to Iceland. Only, he encountered a terrible tragedy: the flight never arrived at its destination.

Prince George, Duke Of Kent FactsWikimedia Commons

38. His Plane Went Off Course

George’s plane was an army vessel designed to land on water. Because of this, these particular planes avoided flying over land whenever possible. But for some inexplicable reason, George found himself hurdling over a dangerous stretch of land. Worse still, his plane was headed straight for a crash landing on Eagle’s Rock, a hillside in Scotland. A crash over water would have been survivable. But over land? Impossible.

Prince George, Duke Of Kent FactsWikipedia

39. His Life Came Crashing Down

George’s plane crashed on Eagle’s Rock and because of the fully loaded fuel tanks, immediately burst into flames. Villagers in nearby towns heard the devastating explosion. Sadly, there were 14 fatalities aboard the aircraft and George was one of them. But this wasn’t the end of George’s story—not even close. The fatal crash landing on Eagle’s Rock evolved into a famous conspiracy.

Prince George, Duke Of Kent FactsShutterstock

40. His Demise Is A Mystery

The pilot of George’s fateful flight was none other than the very experienced Flight Lieutenant Frank Goyen. This begged a pressing question: Why was he flying over land when he could have been flying over water? Due to clear conditions, he had no reason to be flying off course. But there’s more to the mystery…Even the flight plans magically disappeared.

Prince George, Duke Of Kent FactsWikimedia Commons

41. He May Have Been At The Wheel

George was a certified pilot but not the official pilot on the trip that ended his life. Some rumors suggest that George, maybe using his push as a royal, talked the pilot into letting him take the wheel. The rumors go even further and get much wilder. Since George was a party Prince, some believe that his inebriation led to the crashing of the plane. But there’s even a darker theory than that.

Prince George, Duke Of Kent FactsWikipedia

42. He Humiliated Them

George’s personal life had clearly spiralled out of control. His rampant affairs and fraternization with spies—not to mention, his drug use—embarrassed Britain. It’s pretty clear that a dead George would be far less trouble to the British Government than an alive George. But would the government go so far as to crash a plane just to get rid of one royal pain? Some people say: absolutely!

Prince George, Duke Of Kent FactsGetty Images

43. He Handcuffed Himself

Adding even more mystery to the crash was what rescuers found hand-cuffed to George’s wrist. It was an attaché case filled with money—more specifically—Swedish Kroner. This led many to wonder: if the flight was heading to Iceland, why was George carrying Swedish Kroner? One theory suggests that George and the other passengers were on their way to Sweden for secret peace talks with the Germans.

Greta Garbo factsShutterstock

44. There Was Only One Survivor

14 people perished on George’s final and fatal flight, but there were 15 people on board. The lone survivor, Andy Jack, was the only one who could say what actually happened on that flight. He somehow survived the plane’s terrifying crash and ran to a nearby house for safety. But this was strictly against protocol as Jack was supposed to stay with the wreck...

So let’s hear what Jack had to say. Let’s finally solve this mystery once and for all.

Timur FactsShutterstock

45. They Buried His Truth

Andy Jack could’ve told the story of George’s tragic flight, but the British Government forced him to sign a document promising not to tell anyone what happened. Jack kept his word, and after retiring with a good pension, he drank his money away. At the youthful age of 57, he passed on from cirrhosis of the liver. And just like that, Jack took the secret of George’s fatal crash to his grave.

Prince George, Duke Of Kent FactsShutterstock

46. He Remains Locked Away

As we've seen, George was a love letter writer and some of them had to be quickly hidden from the public eye. But what happened to all that lusty correspondence? Rumor has it, George's eye-opening file remains locked up in Windsor Castle. Besides love letters, there could also be proof of his espionage or even some desperately needed information about his mysterious demise. Unfortunately, no one’s allowed to see it.

Castles FactsPixabay

47. He Fathered Some Secrets

Between the partying, the drugs and the threesomes, George and Kiki Preston allegedly had a child together. Michael was born in 1926, and was quickly adopted off to the American publisher Cass Canfield who ran Harper & Brothers. There is no record of George acknowledging the birth, but years later, even his brother Edward didn’t attempt to deny it.

Confucius FactsShutterstock

48. He Had A Kennedy Connection

George’s supposed son, Michael Temple Canfield, may have known nothing of his royal background, but it was definitely in his blood. Even though he grew up in the US, he managed to find a high society woman to hook up with. Michael married Caroline Lee Bouvier, who you may know as the younger sister of JFK’s wife, Jacqueline Kennedy. Pure American royalty.

Lee Radziwill factsFlickr, Kristine

49. All Roads Lead To Royalty—And Tragedy

One of George’s many affairs was with romance author Barbara Cartland, a married woman. Ostensibly, George and Cartland had an illegitimate daughter who was born in 1929. Cartland named her daughter Raine and eventually, through marriage, she became Raine Spencer. Does that name sound familiar? Sure does—she’s the stepmother of the doomed Princess Diana.

Prince George, Duke Of Kent FactsGetty Images

50. His Funeral Was Emotional

Say what you will about George’s antics because, in the end, everyone adored him. Royal funerals can often be cold, laborious affairs, with little emotion on display. George’s funeral was another story. Even his brother, the King, fought to hold back tears. George’s wife Marina, when she approached her husband’s casket, fell to her knees and sobbed freely, pouring forth her insurmountable grief.

Prince George, Duke Of Kent FactsGetty Images

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16

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