Think Cara Delevingne is scandalous? Meet her great-aunt, Viscountess Doris Castlerosse.
1. She Was “The Mistress Of Mayfair”
It’s a rough life when you social climb your way into history, and no one knew that better than Doris Delevingne, the Viscountess of Castlerosse. Nicknamed the “Mistress of Mayfair” for the sheer number of beds she ruthlessly seduced her way into around London, Castlerosse was the most scandalous courtesan of her time.
The details of her lovers still shock people today, not to mention the sordid secrets of her marriage. But in the end, she paid an appalling price.
2. She Had A Scraps To Scandal Story
Although she came from humble beginnings (her father was a French hat maker in London), Doris Delevingne knew what she wanted early in life. At the age of 18, she began working just next to the high and mighty of England, selling used gowns to actresses. But for Doris, who was blonde, beautiful, and fine-featured, this was only a stepping stone.
She found her next step up very quickly.
3. An Actress Pulled Her In
While working in this dress trade, Doris met the person who would change her life. Actress Gertrude Lawrence invited Doris to room with her in the posh neighborhood of Mayfair, and it gave Doris a whole new perspective on life.
Lawrence was the mistress of a Cavalry Officer, and had fancy cars, elegant parties, and constant jewels at her command. Suddenly, Doris began to see just how cushy the world of a kept woman was. This wasn’t a good thing.
4. She Was An Addict
There’s certainly no shame in a woman making it into society any way she could, but Doris Delevingne wasn’t most women. In short order, she became positively addicted to Lawrence’s kind of lifestyle. Around this time, she apparently liked to touch her head, then her neck, then her decolletage with the mantra “Tiara, brooch, clip, clip”.
She was ravenous for extravagance, and she knew just how to get it.
5. She Became A Kept Woman
It wasn’t long before Doris took a page out of her friend Gertrude’s book and snagged herself a wealthy lover of her own. While trawling the uppity clubs in town, her first major conquest was the American millionaire Laddie Sanford. The terms of their relationship were very clear from the beginning.
Sanford gave Doris a new house, an allowance big enough for her to buy a Rolls Royce, and her own personal maid. And what did Doris give in exchange? Well…
6. She Was Good In Bed
Doris was an unabashed social climber, yes, but her determination wasn’t the only key to her success. She had a very dirty secret weapon. Not to be too delicate about it, but word got around fast that Doris was a dynamo in the sack. She even had her own signature move, ”Cleopatra’s grip,” though its details are unclear and probably best left to the imagination anyway.
Unfortunately, no matter how good she was in bed, she was also turning into a monster.
7. She Was Cruelly Thoughtless
Doris’s bedroom appetites were only matched by her need for constant material comforts. On Sanford’s bill, she insisted on ordering Italian shoes 250 pairs at a time, since she believed it was “Idiotic to wear shoes more than three or four times”. She was even more flippant about her Parisian silk stockings; those she only wore once before chucking them.
But her gravy train was about to break down.
8. Her Lover Dumped Her Horribly
Whatever Doris’s carnal charms, Laddie Sanford didn’t stay captivated for long. One day, he inflicted a heartless insult. He not only struck up an affair with the beautiful—and noble, and rich—Edwina Mountbatten, he up and left Doris in the process. Sure, Doris still had her house and her fancy things, but she still needed a cash influx.
She came up with a shrewd but chilling solution.
9. She Went To The Dark Side
Around this time, Doris moved from being a kept woman to becoming a full-on courtesan of the demi-monde. She filled her schedule (and her four-poster) with a rotating stable of men, usually the profligate sons of the aristocracy. No less than Prince George, son of King George V, “got into trouble” for carousing at one of her raucous parties.
For Doris, the slide down to the underworld of London was soft as silk. That didn’t mean it wasn’t dangerous.
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10. She Developed Another Trademark
Doris now had to live on her wits and beauty alone, and that wasn’t as easy as it looked. She became a regular fixture at clubs like Café de Paris, hoping to attract rich men into her silken web. She even developed another trademark—people called her “The Girl With The White Gloves,” because she took to wearing classy white opera gloves wherever she went.
It was as good a calling card as any, and she soon landed her next meal-ticket, the Canadian stockbroker Sir Edward Edgar. She just didn’t land him for long.
11. She Ruined A Man
Doris now had permanently expensive tastes, and any man who wanted her had to pay through the nose. Of course, with a reputation like hers in the boudoirs, many a gentleman like Sir Edward Edgar were willing to pay this price of admission. It ended in his destruction. Before long, Edgar filed for bankruptcy, no doubt in partial thanks to Doris’s demands.
So Doris was alone again…and she was about to enter her truly infamous era.
12. She Met A Notorious Noble
At 28 years old, Doris met Valentine Browne, the Viscount Castlerosse. But don’t let his fancy name fool you—there was perhaps no noble more notorious in London than the Viscount. As a gossip columnist for the Sunday Express and lackey to the sly, oily press magnate Lord Beaverbrook, Castlerosse was an expert in sleaze.
Except that was just the beginning.
13. Her Lover Was Ugly
Where Doris was all moon-faced beauty, the Viscount Castlerosse was…not. Don’t go picturing a romance hero swooping Doris off her feet. Instead, Castlerosse was overweight, balding, and generally considered something of a social failure in polite society. Which, well, you might have guessed from the whole “Viscount acting as a gossip columnist” thing.
Forgive me though, I know I’m being shallow. The Viscount’s personality was even worse.
14. Her Relationship Was Terrifying
From the moment he saw Doris, the Viscount wanted to have her. Doris, knowing a paycheck when she saw one, obliged—but refused to make him her one and only. The Viscount’s reaction was chilling. When constantly sending expensive gifts her way didn’t tame her, Castlerosse pilfered the key to her house and let himself in whenever he pleased.
Doris, for her own bizarre reasons, didn’t seem to mind. Then the dysfunction truly hit.
15. She Attacked Her Lover
Doris was no pushover, and Castlerosse was a man clinging hard to his failing sense of superiority. It was a very bad combination. When they fought, it often turned into something more like a blowout bar fight than a lovers’ quarrel, with Doris biting and scratching at her beau anywhere she could. Only, she never expected the Viscount’s savage retaliation.
16. She Received A Brutal Punishment
The first time one of these fights happened, Doris was in for the shock of her life. For when she bit and clawed the Viscount, he hit back. With Doris walking around London visibly bruised, the Viscount’s boss Lord Beaverbrook had the decency to shame the man for it—but Castlerosse merely rolled up his trouser legs to reveal his own wounds, as if he were absolved.
Yet their other problems, though less visible, were more powerful.
17. His Mother Hated Her
Doris and her Viscount were a match made in the fires of Hades, but they just couldn’t seem to quit each other. This developed into a scandal. Castlerosse came from an uppity Irish Catholic family, and his battle-axe mother, Lady Kenmare, disapproved of Doris on the grounds that she was neither Catholic nor classy.
But, Doris being Doris and the Viscount being the Viscount, they had to go and spit in everybody’s faces anyway.
18. She Kept A Ruinous Secret
In 1928, Doris and the Viscount went down to the Hammersmith Registry Office and made it official, marrying in a quick and dirty ceremony. It was a top-secret turn of events, especially since the Viscount didn’t want his mommie dearest finding out about it.
For a short time, they walked around town, smug and satisfied that they’d pulled one over on his family. But they paid the piper back tenfold.
19. Her World Fell Apart
Doris had her own kind of street smarts, sure, but the couple as a whole weren’t exactly geniuses. Of course the Viscount’s well-connected mother found out about the union, and of course her reaction was unhinged: She cut the Viscount off completely from his inheritance.
Suddenly, Doris, realized she’d backed the wrong thoroughbred. Her next decision was easy.
20. She Betrayed Him With A Blink
For the newly-minted Doris Castlerosse, everything had a price. Even her marriage. So when the Viscount’s mommy greatly reduced his circumstances, Doris performed a cold-hearted act in an instant. She began taking right back up with a slew of other men—ones who had the means to fund the lifestyle she wanted.
And she debased herself further.
21. She Was An Awful Friend
Men weren’t the only source of Doris’s income. She also dabbled in other nefarious activities, including selling out her famous friends. See, the Viscount’s boss Lord Beaverbrook had gossip rags to run, and he paid Doris to be a “society spy” and spill the beans on the goings-on of the aristocracy. She happily took his money and performed the slimy duties.
It was a treacherous game…just not as treacherous as her husband.
22. She Dated Politicians
Soon, Doris seemed to be sleeping with half of London, and she was none too discreet about it. With so much gossip going on about her, it wasn’t long before her husband tracked all her movements and the members of her little black book. But when she took up next with the Conservative MP Sir Alfred Beit, the Viscount absolutely snapped.
23. Her Husband Made An Infuriating Discovery
At the climax—pun intended—of Doris’s affair with Alfred Beit, Viscount Castlerosse appears to have burst right into the room, catching them red-handed. His next actions were nearly beyond imagining. He began to beat Sir Beit so hard with his walking stick, Doris cried out “Murder!” from the sidelines.
Maybe this was a turning point, because Doris moved on to a different breed of man entirely.
24. She Thought She Could “Cure” Her Friends
Doris’s whole identity seemed to revolve around her bedroom prowess, and she even liked to proclaim, “There’s no such thing as an impotent man, just an incompetent woman”. This led her to a ridiculous conclusion: She began to believe she could “cure” a man’s homosexuality, just by being herself. As you might imagine, this had bizarre and sordid consequences.
25. She Took Up With A Boy Toy
Obsessed with the idea of turning a man straight through her (admittedly impressive) sheet skills, Doris went to great lengths to “convert” the very gay Robert Herber-Percy, known around town as “Mad Boy”. Her methods were mind-boggling. As a 25th birthday present, Doris bought Herber-Percy a room at the Ritz. When he opened the door, his jaw dropped.
26. She Gave Him A Disturbing “Gift”
Once in the room, Doris “presented” Herber-Percy first with a woman she’d hired off the streets, and then with a whip. Her next words were utterly chilling. As a part of her unorthodox cure, she wanted him to whip the woman until her last breath. How would this change things? Your guess is as good as mine. But Doris’s companion shocked her.
27. She Was Vicious
Doris Castlerosse was not someone you said no to, but Robert Herber-Percy did try, bless his soul. He only made a half-hearted attempt at hitting the poor woman—and in turn had to witness a horrific sight. Frustrated, Doris snatched the whip from him and began to do the job herself, giving the woman a welt. She then snapped, “I haven’t wasted my money for this”.
Yes, she was that terrifying. But she was about to meet her match.
28. She Had Ridiculous Goals
In her constant quest to convert gay men, Doris fell in with the celebrity photographer Cecil Beaton. This time, she was as bizarrely tender with Beaton as she was shockingly cruel with Herber-Percy. In order to “seduce” Beaton, she left tuberoses on his bed, and told him to “think of his sister’s wedding” while in the act.
Still, she was about to learn that her lovers could be cruel right back to her.
29. She Got A Taste Of Her Own Medicine
Beaton would later admit that in this relationship, it was he who treated Doris badly, not the other way around. Although he gave her the memorable nickname “Doritzons,” he obviously wasn’t quite converted to her, er, way of life, and eventually dumped her.
This wasn’t something Doris was used to, and her ensuing conquest had more than a whiff of a rebound.
30. She Slept With Winston Churchill’s Son
Around this time, Doris struck up an affair with Randolph Churchill, who was the spitting image of his father Winston Churchill with none of the elder’s goodness or good sense. To everyone who knew him, Randolph was an oaf, a cad, and lush who drank double brandies from the age of 19. In other words, he was perfect for Doris, who adoringly nicknamed him “Fuzzy Wuzzy”.
As we’ll see, this relationship would get even more scandalous, but for now Doris had a quite different matter to deal with.
31. Her Marriage Hit A Snag
I’m sure it will shock absolutely no one to hear that by the 1930s, Doris and her husband were estranged from one another. They were also in a huge bind. Divorce back then wasn’t so easy to come by. Though the courts needed adultery in play—which Doris had plenty of—they also needed her to prove it, along with evidence of their estrangement, which was more difficult.
Doris’s solution to all this was…unorthodox.
32. She Had To Fake Her Real Life
To “prove” her adultery, Doris first roped in many of her lovers to act as co-respondents in the divorce case. Ok, check. Then, she needed to show she’d been far away from the Viscount for a good long while. To fulfill this, she took a trip around the Orient, taking up with a man named Sir William Rootes for good measure. Only, Rootes was hiding a dirty little secret.
33. Her Husband Paid Off A Ringer
In the middle of her whirlwind affair with Rootes, there was something Doris didn’t know. He was a very good friend of her estranged husband, and many believe it was Viscount Castlerosse who put Rootes up to it, just to ensure the upcoming divorce proceedings were airtight.
Only, Doris seems to have found out about this, because her next act was pure vengeance.
34. She Was Ruinously Spiteful
Doris was miserable in her marriage, yes, but she hated her husband so much she couldn’t resist some good old mutually assured destruction. After the Rootes debacle, she found out where the Viscount was staying, let herself into his room, and jumped into his bed—all so that they couldn’t prove to the courts they were estranged anymore.
Did this mean Doris had to stay married even longer to a man she despised? Sure. But, you know, revenge. And anyway, Doris had a new escape route…
35. She Romanced A Woman
Doris had tried changing gay men to her team, and now she took up her own same-sex affair, becoming the kept woman of American millionairess Margot Hoffman. For years, Hoffman showered Doris with gifts ranging from a Palazzo in Venice to aristocratic portraits. And that wasn’t the only way Doris found herself on top.
36. She Had A Comeback
With Hoffman on her arm, Doris Castlerosse had another change in fortunes. In the thick of her marriage to the Viscount, Doris’s social cache fell, but with Hoffman she found herself the toast of the town again, and even attended King George VI’s coronation.
As she quipped of this time, “I much prefer the life I am leading. Takes half the effort and earns twice the money”. Well, be careful what you wish for.
37. She Finally Got What She Wanted
At long last in 1938, Doris and the Viscount really, truly, actually divorced. They had been together nearly a decade—and had been trying to split for practically that entire time. Conveniently (for Doris), their official split coincided with WWII starting, and she took the opportunity to run to the safety of New York with Margot Hoffman.
It should have been a cushy way to wait out the conflict, but Doris had to go and ruin it.
38. She Used Her Lover
Margot Hoffman was desperately in love with Doris, but Doris’s reasons were much darker. Like all her conquests, she cared first and foremost about Hoffman’s pocketbook. There is little evidence she loved Hoffman at all, or that she was a lesbian except via opportunism.
Eventually, this indifference wore even on the devoted Hoffman, and she made a devastating break.
39. She Got What She Deserved
Soon after Doris came to Manhattan with Hoffman, her cash cow got some self-respect and dumped her, leaving her in the lurch. With no man to fall back on, age fast approaching—she was now in her 40s—and a foreign country all around her, Doris had to come up with a backup plan, fast. As it happened, that backup plan had a very familiar face.
40. She Couldn’t Quit Him
Vulnerable and lonely, Doris went back to that same old well: the Viscount Castlerosse. She had been corresponding with him for some time while over in America, and now applied all her charms to the missives. His letter in response made her heart race. Proving that the two them hadn’t learned a dang thing, the Viscount asked Doris to marry him again.
This, time, however, Doris didn’t have the upper hand. She just didn’t know it yet.
41. She Was Getting Played
While Viscount Castlerosse was writing to his ex-wife, he was also romancing another woman—Enid, Viscountess Furness, an Australian heiress who was infamous in her own right. After all, if Doris could play the field, why couldn’t he? Perhaps, however, Doris sensed this in some way, because she began planning a hasty trip back to Europe to reunite with Castlerosse. A very hasty one.
42. She Called In An Infamous Favor
It was no cake walk to get back to Europe from America in the 1940s, especially in the middle of a war. To help her along the way, Doris did two things—both of which were scandalous. First, she somehow managed to convince Prime Minister Winston Churchill to help her secure air passage over. How? Well…we’ll get to that shortly.
But it’s what she did next that was her downfall.
43. She Made A Desperate Choice
At this point, Doris had almost entirely run out of money. To supplement her non-existent income, she pawned some of her diamonds, though she hadn’t yet received payment for them when Churchill sent over her plane tickets.
Full of hope, she set off for her homeland of England and anticipated walking into the arms of her ex. That hope was gravely misplaced.
44. She Tried To Hide The Truth
When Doris got off the train she took into London, Viscount Castlerosse was waiting to meet her in the darkened station. He then drove her to the Dorchester hotel, but when she stepped into the building his jaw dropped. Now that she was in the bright lights, he realized time had not been kind to the courtesan.
Her partying had turned her beauty—perhaps her only asset—into a cheap, haggard imitation of its former glory. The Viscount turned cold-hearted in an instant.
45. Her Ex Abandoned Her
After seeing Doris’s current state, the Viscount stayed only for a perfunctory dinner, and then went right back to his Viscountess Enid, resolving never to see Doris again. It gets more depressing: Doris was no fool, and she knew that her ex-husband was high-tailing it out the door. This is where everything came full circle.
46. She Committed A Crime
With her future now so uncertain again, Doris naturally began to think of that money she was owed from the pawnbroker who took her diamonds. Unthinking, she telegraphed them about the cash—little knowing she had just sealed herself into a dark fate. In WWII, selling assets like diamonds was against the law, and Scotland Yard was reading her telegrams with great interest.
They acted very quickly from there.
47. She Hit Rock Bottom
With Doris so flagrantly breaking the law, officers were at her door in short order, questioning the socialite on what, exactly, she thought she was doing. Although they didn’t immediately charge her and left her rooms, Doris nonetheless began to panic. Visions of a drab, penniless life behind bars danced in her head.
With no friends she could call, and no lovers to manipulate, she believed she only had one tragic option left.
48. She Met A Tragic End
On the 12 of December 1942, Doris Delevingne took a fatal overdose of sleeping pills at the Dorchester Hotel. She was just 42 years old when she passed but left behind enough scandal for three lifetimes. In fact, her scandal still continues: Model Cara Delevingne is her great-niece.
But there is still one secret about Doris that historians hotly debate.
49. She Slept With A Father And His Son
Doris’s steamy liaison with Randolph Churchill is practically a matter of public record. But her affair gets more sordid than that. According to a source close to the Churchill family, Doris also had a fling with Randolph’s father, Winston Churchill, when he was not yet Prime Minister. And though some scoff at this thought—many see Churchill as staunchly loyal to his wife Clementine—there is some big evidence.
50. She Had A Scandalous Portrait
Besides the fact that it was Winston who helped Doris get out of America and back into Europe, the future Prime Minister also painted two portraits of the courtesan—when he had previously only painted his wife. Some even say that Doris kept one of the painting as collateral, and that one of Winston’s aides had to sneak into her hotel room after her passing to find it and remove the evidence.