On the surface, it seems like socialites like some of the most glamorous lives out there. They have all the fame and luxury of a royal or a movie star, without any of the work. But behind the gilded curtain, there are countless tales of scandal, intrigue, tragedy, affairs, and crime. These socialites may have thought they were hiding sordid secrets—but even their most twisted stories are out in the open now.
1. Barbara Baekeland Was The Most Twisted Socialite Of All
We're not about to start off easy and then save the most disturbing story for last. No, we're diving headfirst into the madness. Barbara Daly Baekeland lived a fantasy life of glamorous parties, wealthy admirers, and Hollywood starlets. Her incredible beauty got her into some of the highest echelons of society—but behind that exquisite face, she was hiding a terrible secret, and it was one that would drive her to an utterly gruesome act.
2. She May Have Faked A Pregnancy
In the 1940s, Barbara fell for Brooks Baekeland, the grandson of a wealthy inventor. They were getting hot and heavy, but that didn’t seem to be enough for our girl. According to one report, she lied and told Brooks that she was pregnant in order to push him into a quickie wedding. It worked, and suddenly Barbara went from hungry social climber to high society socialite in her own right.
In the short term, this was everything Barbara wanted. In the long term, though, this would lead to all-out carnage.
3. Her Marriage Was Falling Apart
In 1946, Barbara got pregnant for real this time, giving birth to a baby boy she named Antony. It couldn’t have come at a worse time. At this point, both Brooks and Barbara were cycling through depressions together, had engaged in several affairs, and were generally miserable. Guess what? A baby didn’t fix those issues. In fact, new ones just started popping up.
4. She Had Gruesome Dinner Parties
As young “Tony” grew into a toddler, the Baekeland heir started to exhibit some disturbing signs. Although Barbara Baekeland was nothing if not self-absorbed, even she must have seen that her son was in need of some professional help. Her response was blood-chilling. Instead of taking Tony to therapy, Barbara insisted on pretending everything was fine. In fact, she once “proudly” showed her dinner guests a series of drawings Tony had done. Their subject matter? Oh, just bloody human figures.
And yet, for all that Barbara’s relationship with her son was dysfunctional, her marriage was also a real piece of work.
5. Her Son Rebelled
Later, when he was a teen, Tony ran away with a male lover. Baekeland was far from approving, so she must have breathed a sigh of relief when he finally brought home a girlfriend, Sylvie. Unfortunately, her presence was about to blow up in all of their faces. Baekeland's husband quickly started an affair with Sylvie. Yup, his own son's girlfriend. And this wasn't just a fling, nope. He actually filed for divorce from Barbara.
6. She Tried To Reset Her Life
In 1968, Barbara’s already dramatic life came to a screeching climax. That year, fresh off her divorce from Brooks Baekeland and mired in a panic over her son’s sexuality, Barbara took Tony on a summer vacation to Majorca to unwind and get away from the world. Instead of relaxing, however, Barbara committed an act she could never go back from.
7. She May Have Slept With Her Son
Although some of the details are necessarily hazy, it was in Majorca that Barbara and Antony likely began a physical, incestuous relationship after a series of intimate, candle-lit dinners. The details are skin-crawling. Sickeningly, Barbara supposedly believed she was doing Tony a favor by finally showing him what a real woman could do.
Of course, it didn’t take long for her horrific plan to unravel. When they returned home from their vacation, Tony descended into madness, spending time in and out of psychiatric facilities.
8. Her Son Attacked Her
On November 17, 1972, Barbara was making dinner in her family flat when she got into yet another argument with Tony, this time about a friend Tony wanted to invite over who she didn’t want to see. This small spat pushed Tony over the edge, and he finally made good on all the dark omens. He took a kitchen knife, charged toward his mother, and stabbed her directly in the heart.
9. She Died Instantly
Barbara’s end was instant, and she probably had no time to even understand what was going on. But Tony’s response was so disturbing, it’s impossible to forget. The Baekeland heir was so out of it, he ordered a Chinese takeout meal directly after slaying his mother, and was still munching on it when he calmly called the authorities to turn himself in. Yikes.
It's quite a twisted story, right? Few can top it—but if people refer to what you went through as the "Trial of the Century," as they do with Evelyn Nesbit, you can bet it's juicy...
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10. Evelyn Nesbit Was At The Center Of The "Trial Of The Century"
While Evelyn Nesbit's famous features made her the darling of the Gilded Age, her dark secrets mirrored the era’s roiling undercurrents. Her undeniable beauty enchanted the masses, but for one man, it inspired a chilling, deep-seated obsession—one that ultimately led to a crime so dark, it's impossible to forget.
11. She Was A Head-Turner
Evelyn Nesbit had a flourishing career as a high-profile model, but she desperately wanted to act. During a play, she caught the eye of a hot-shot architect named Stanford White. He became so consumed by Nesbit’s performance that he returned to see the play over and over again. Some sources said he attended over 40 times. His adoration rapidly devolved into a possessive obsession. And it gets more disturbing from there...
12. She Couldn’t Remember What Happened
One night, 48-year-old White invited 16-year-old Nesbit to a party at Madison Square Garden—but he was actually pulling the oldest trick in the book. No one was there except for him, and he plied her with champagne. The next morning, Nesbit woke to find herself reflected in one of the many mirrors—exposed and lying undressed next to Stanford White. With no memory of the night’s proceedings, she let loose a blood-curdling scream.
White’s manipulative scheming found fruition. He had claimed her body for himself. He told her that she belonged to him now.
13. He Wasn't The Only One
White wasn't the only man who was obsessed with Nesbit. Along the way, she picked up another admirer. His name was Harry Kendall Thaw—a coal and railroad baron with a whopping $40 million fortune. When Nesbit and her mother found themselves in dire financial straits, he swooped in. He took her on a trip to Europe to help her relax, and while they were there, she told him her darkest secret.
Nesbit confided in him about the night when White had taken advantage of her. Thaw was furious—but also strangely compelled. He asked her for all the dirty details. At first, Thaw's concern moved Nesbit, but later on, it took a dark turn.
14. He Was Terrifying
One night while they were in Germany, Nesbit awoke to see Thaw standing over her with a whip in hand. He brutally attacked and raped her. The next day, he pretended as if nothing had happened. While eventually, she found her way home, it left her more unmoored than ever. For the next two years, Thaw did everything in his power to make amends for brutally attacking Nesbit.
And eventually, to Nesbit's eternal woe, he wore her down. They tied the knot in 1905—but their wedded "bliss" was brief.
15. He Attacked Her Attacker
A year after they got married, Thaw planned a grand trip for Nesbit. It began with a pit stop in New York—where Thaw enacted his dark plan. He brought Nesbit to Madison Square Garden, where they inevitably ran into Stanford White. There, Thaw drew a pistol from his coat, took aim at his nemesis, and shot him point-blank. Three deadly blasts rang through the theatre. With bullets to the teeth, the eye, and the shoulder, White died instantly.
Smiling and victorious, Thaw gave up his weapon and said, “I did it because he ruined my wife.”
16. She Was The Star Witness
Because she was the center of this twisted love triangle, Nesbit became the star witness and the face of the salacious trial that ensued, which journalists nicknamed the "Trial of the Century." Her defamatory information on Stanford White was evidence for her husband’s defense—a plea of temporary insanity. But eventually, when his family abandoned her, she turned on him and began to testify against her own husband at his sanity hearings.
Eventually, Thaw filed for divorce—finally releasing Nesbit from the gilded cage that he and White had trapped her in for years. That divorce was a blessing...the same can't be said for what happened to Hui-Lan Koo...
17. Hui-Lan Koo Faced Heartbreak Like No Other
In the golden glamour of the Jazz Age in the 1920s, perhaps no beautiful socialite was as celebrated as Hui-lan Koo, AKA, Madame Wellington Koo. Born Oei Hui-lan, the Indonesian heiress rose to prominence in all the best parties of her day for her elegance, her intelligence, and her eccentricity. Yet behind the mask of her beauty, Hui-lan hid a dramatic life that was equal parts scandal and tragedy.
18. She Had A Romance With A Much Older Man
When she was still a teenager, Hui-lan met and began to court the British consulate agent Beauchamp Caulfield-Stoker, who—as you can probably guess from his double-barreled name—was about as stiff-upper-lip British as they come and nearly two decades older than her. They tied the knot and moved to England. With the location change came a newfound freedom for Hui-Lan. Aside from taking part in high society parties, she also got into aviation and driving—unconventional activities for a young lady.
However, Beauchamp Caulfield-Stoker had wanted a naïve girl to bring home, and he was aghast at his pretty little Asian bride’s transformation into a ballsy society maiden
19. She Became A Mother At The Worst Time
When Hui-lan became pregnant, she hoped the child would save her marriage. Sadly, she was wrong. Her husband did basically everything in his power to get away from her, taking jobs that would give him an excuse to leave her behind. When he was gone, he would barely contact her. By 1919, she couldn't take it anymore. She filed for divorce—and the paperwork revealed one final, brutal indignity.
20. Her Husband Kept A Huge Secret
Like so many scorned wives before her, Hui-lan cited “cruelty” and “misconduct” as her grounds for divorce—only that was far from all. In a jaw-dropping admission, Hui-lan also claimed that Beauchamp had point-blank refused to introduce her to his family throughout the entire decade they had been married. Um, WHAT? Throw out the whole man, Hui-lan. She began her new life as a single woman—not that that lasted long.
21. She Had A Meet-Cute
Hui-Lan's mother wasn't about to let her daughter live life as a divorcee, so she acted as matchmaker. The man she came up with was Wellington Koo, a Chinese diplomat. From there, it was a whirlwind. And this one seemed like it would stick. First engagement, then marriage, then two sons. In 1923, the couple moved to Beijing while Wellington Koo briefly became the Premier and interim President of the Republic of China.
Yep, for a hot minute, Hui-lan was the First Lady of China. Then tragedy came for her.
22. He Left Her
The outbreak of WWII meant that Hui-lan was separated from her husband for long periods of time, and ultimately, they couldn't survive the distance. But Hui-lan couldn't accept the hand that fate had dealt her. She continued to insist that “I am Madame Wellington Koo, head of the family.” Sadly, Hui-lan outlived not only her two ex-husbands, but also, her three children.
The life of Hui-lan Koo spanned across a literal century, and she went from one of the most popular women in the world to a life of devastating loneliness. While two heartbreaking divorces is one thing, how about a man who leaves you—and the crown—behind? That's what Thelma Furness had to deal with...
23. Thelma Furness Was The Woman Before Wallis
Edward VIII’s marriage to Wallis Simpson is something straight out of a romance novel, but Simpson wasn’t the future king’s only famous mistress. That (extremely) dubious honor also goes to Thelma Furness, the aunt of the infamous Gloria Vanderbilt. The craziest part? Furness’s life is just as wild, if not wilder, than the lives of the famous figures around her.
24. She Married The Love Of Her Life
Thelma suffered a terrible and brief first marriage before meeting a man named Marmaduke Furness. He was everything she wanted. On June 27, 1926, the two tied the knot in a small, private ceremony, surrounded only by close friends and family. Thelma felt like she had it all: someone that loved her and who she loved in return, money, power, and fame. But then life threw her a curveball the very next day...
...She met another man—one who would make infamous.
25. She Met The Future King
The next day, Thelma—now a Viscountess—received an invitation to a party hosted in Londonderry. The most nerve-wracking part? The Prince of Wales, Edward VIII himself, was attending. When Thelma laid eyes on him, she thought him very handsome—but their infamous affair didn’t start right then and there. That happened three years later, when Thelma's husband pushed her over the edge.
26. She Grew Suspicious
Rumors began to swirl that Marmaduke was being unfaithful, but Thelma ignored these rumors. After all, the penalties for divorce in England were severe, and moreover, her husband loved her with all his heart. Eventually, the rumors became too much for Thelma to handle. Marmaduke's daughter from a previous marriage sensed how depressed Thelma was, and invited her out to the Leicester Fair. She accepted her stepdaughter’s act of kindness and tried to enjoy herself. And that's when fate stepped in.
She bumped into someone she never expected to see again: the Prince of Wales himself.
27. She Fell In Love
They talked and the Prince invited her out for dinner and dancing. With her heart pounding in her chest, she accepted. Thelma's first private meeting with Edward was like something out of a dream. They met in Edward’s private sitting room, where they talked and drank. In her own words, “The admiration in his eyes as we danced, the frank, disarming way in which he spoke…quickened my heart.”
Before she knew it, Thelma had fallen deeply in love with Edward. They spent long romantic weekends together at Fort Belvedere...but the good times can't last forever.
28. She Started An Infamous Affair
Sometime between 1930 and 1931, Thelma met someone that changed her life, and that of Edward’s: Wallis Simpson. By her own account, she found Simpson to be an incredibly charming and fun person to be around. According to Thelma, she even introduced Edward to Simpson as a friend of hers! Although Thelma didn’t know it at the time, she had just doomed her own relationship with Edward, and things with her husband weren’t going too well either.
29. Her Marriage Didn’t Work Out
Marmaduke Furness asked Thelma to visit him in Nairobi, and although she was confused, she decided to give it a shot. He was attentive to her and kind…for a while. Quickly, his old habits slipped through the cracks, and the frequent arguing started up again. Soon enough, both Thelma and Marmaduke came to an earth-shattering realization: There was simply no salvaging their marriage. The two separated, and she returned to Edward.
Upon telling Edward of the news, the two were incredibly joyful—but there was also an undercurrent of sadness.
30. She Didn’t Want To Be Queen
Thelma knew in her heart that marriage to Edward was impossible. Edward would, one day, be the king, and would bear an incredible amount of responsibility along with the title. Obviously, he wouldn’t—couldn’t—marry her. In the moment, though, she was just happy to be with someone who loved her and whom she trusted. Unfortunately for Thelma, she trusted Edward perhaps a little too much.
31. She Unwittingly Destroyed Her Relationship
In January 1934, Thelma’s twin sister invited her to California for a visit. The trip would take roughly five or six weeks. She immediately prepared for the trip, but Edward was less than happy to be away from her for so long. That’s when Thelma had a stroke of genius: she asked her good friend Wallis Simpson to keep Edward company.
Of course, Simpson took Thelma's request a little too literally…
32. They Betrayed Her
When Thelma returned to Edward, she could tell something was off. She went to her "friend," Simpson, for advice...and suddenly, everything clicked into place. While in the middle of inviting Simpson for a couple’s weekend getaway, Simpson received a direct phone call from Edward. For Thelma, the alarm bells were already screaming. Then, during their weekend get-together, she noticed all the secretive little glances shared between Edward and Simpson.
At that moment, Thelma knew that both of them had betrayed her, and she wouldn’t stand for it.
33. She Got Her Revenge
Angry at the Prince for stabbing her in the back, Thelma got a bit of her own revenge. She started seeing Prince Aly Khan. Khan was the perfect escape for her; he was adventurous and perpetually untroubled. Khan allowed Thelma to bury her heartache deep into the back of her mind, but the relationship didn’t last; eventually, they drifted apart. Thelma felt more alone than ever—but she still had one person to lean on.
For Thelma, men had only led to heartbreak, but she always had her twin sister. In the decades that followed, they were inseparable.
34. She Never Forgot Him
On January 29, 1970, at the age of 65, Furness passed away while she was on the way to see her doctor. According to her niece, Gloria Vanderbilt, “In [Thelma’s] bag was this miniature teddy bear that the Prince of Wales had given her, years before, when she came to be with my mother at the custody trial, and it was worn down to the nub.” Her grave is next to her twin’s in Culver City, California.
The love triangle between Thelma, Edward, and Wallis was one of England's biggest scandals—but Gloria Guinness gives them all a serious run for their money.
35. Gloria Guinness Was A Socialite Turned Spy
Of all Truman Capote’s beautiful socialite “swans,” Gloria Guinness was the most scandalous. Called “the most elegant woman in the world,” by her admirers, Guinness nonetheless hid immense tragedy, infamy, and bitterness beneath her glittering façade—and dark rumors followed her to her immaculate grave.
36. She Became A Countess
After a brief first marriage, Gloria rebounded with Franz-Egon, the Count von Furstenberg. Before long, they tied the knot. Yep, the young, beautiful Gloria was now German nobility—and she soon got into a scandal to match. Dark rumors also surround this part of Gloria’s life. With WWII on the horizon and everything in Germany going upside down, some persistent stories claim that Gloria worked as a spy during this time, all while she posted up in the neutral Madrid and waited out the conflict.
Sounds juicy, but I wouldn’t be too hasty to praise her as a “shero”…
37. She Worked For The Wrong Side
If Gloria’s clandestine spy history is true, then we have to grapple with a very ugly possibility: That she did her espionage work for the wrong side. Among her closest friends, sources say, were Nazi right-hand man Hermann Goring and Adolf Hitler himself. But there's more...
38. She Was Undocumented
It is difficult to think of chic little Gloria Guinness doing the devil’s work for the Axis powers—but it kind of holds water. People like Countess Aline Griffith were also deep into espionage at the time, so it wasn’t unprecedented. Moreover, by the 1950s, some said Gloria didn’t even have a valid passport and was officially stateless. And then there were Gloria’s own confessions.
39. She Was A Liar
At the height of her fame, Gloria wasn’t exactly known for her candor and honesty. Quite the opposite; she was practically a pathological liar. She loved making up baseless stories about her past, claiming her father was a revolutionary (nope) and her mother was a humble laundry maid (also no). Honestly, if this woman wasn’t a spy, she should have been.
40. She Was Almost Royalty
Apparently even super-spy marriages don’t last, because in 1940, Gloria and Count von Furstenberg called it quits and divorced. In classic Gloria fashion, she didn’t wait around long for her Prince Charming—and I mean "Prince" literally. Just two years later, she married Ahmad Fakhry Bey, the grandson of the King of Egypt. Then, when that marriage fell apart in 1949, Gloria really found her destiny.
41. She Became A Socialite
In 1951, she caught her biggest fish yet: banking magnate Thomas “Loel” Guinness. Guinness was supremely high society, and Gloria had finally settled into her "socialite" niche. Granted, it did come with drama. Gloria was her husband’s third wife, and inherited an entire brood of moody stepchildren to go with him. Oh, but that was just the beginning.
42. Her Family Was Scandalous
By the time Gloria married the magnate, Guinness and his family were already notorious for a series of international scandals that followed them around. Most infamously, Loel’s first wife, the beautiful Joan Yarde-Buller, had left him in the 1930s for none other than Prince Aly Khan. Yep, seems like Gloria was definitely Loel Guinness’s type.
43. She Took Many Lovers
Gloria may have looked like the perfect lady—but she hid a scandalous side. She took multiple lovers, many of them married themselves. She also had a type: Powerful and confident. Among her conquests were David Beatty, the 2nd Earl of Beatty, and the carousing British ambassador Duff Cooper. And while high society never kissed and told on Gloria, these lovers definitely did.
Cooper later reminisced about how much of a wildcat Gloria was in the sack, saying, "I have never loved anybody physically so much or been so supremely satisfied.” Now that is a glowing recommendation.
44. She Met A Tragic End
On November 9, 1980, Gloria collapsed from a heart attack and passed in Switzerland, sending shockwaves through polite society around the world. Yet that wasn’t the only tragedy. At 68 years old, she was disturbingly young for her fate—and rumors still abound about the true nature of her end.
45. Her Death May Contain A Secret
When someone beautiful meets an ugly, untimely end, there are often suspicions of foul play. Gloria’s death was no exception. Many of her friends believed that Gloria, bored of her glamorous life and feeling the emptiness of her gilded existence, may have killed herself in a fit of disillusionment. It's definitely a sad ending for such a character.
The rumors of Guinness's spy past followed her beyond the grave—but the rumors that followed Edwina Mountbatten and her husband after their deaths are even more disturbing...
46. Edwina Mountbatten Was A High Society Rebel
Edwina Mountbatten knew better than anyone that behind the glittering, softly lit ballrooms of high society, there were dark, twisting corridors full of secrets—after all, behind closed doors, Edwina had more than a few secrets of her own. From her scandalous marriage to her tragic twist ending, this beautiful socialite lived ten lives in one.
47. She Fell In Love With A Royal
When Edwina was just 19 years old, she met Lord Louis Mountbatten, a relative of the current British Royal Family and a great-grandson of Queen Victoria in his own right. Translation: He was one heck of a catch. Lucky for Edwina, Louis—nicknamed “Dickie” by his family—only had eyes for her, and they struck up a whirlwind romance. It seemed like a fairy tale, but soon after their lavish wedding, the cracks started to show.
48. She Had Strange Kinks
While still on her honeymoon, Edwina unleashed her secret wild side. Although she and Louis were both virgins on their wedding night, it didn’t take long for the socialite to discover she liked falling into bed very much. So much, in fact, that she reportedly begged Louis to take her to Paris for the explicit purpose of getting it on in “the most awful places we could find.” Louis, however, had a much different reaction.
Louis, ambitious for a career in the Navy, thought of marriage as a “smug diversion” from his real goals and reportedly considered intimacy as an awkward mix of “half hydraulics and half psychology.” That's not a good sign...
49. She Betrayed Her Husband
After the birth of her daughter Patricia, Edwina Mountbatten went off the deep end. One day while Louis was away in the Navy, she packed up her babe with a nanny and sent her off to the coast so she could have some Mommy alone time. Only, she wasn’t so alone. Edwina proceeded to spark up a string of affairs with society’s most eligible bachelors. And somehow, this wasn’t the most scandalous detail.
50. She Had Several Lovers At Once
Once Edwina decided to jump the Good Ship Fidelity, she really went for it. She not only took lovers, she took them near-simultaneously, hopping around town with a Lord Molyneux in the morning, the dashing polo player Laddie Sandford in the afternoon, and newspaper editor Mike Wardell in the evening. It wasn’t long before it got messy.
51. She Broke Her Husband’s Heart
When Louis first realized the extent of Edwina’s double life, he was “devastated,” but he also had to think practically. As a member of the royal family, he could hardly divorce her without causing an uproar. So instead, they came to a scandalous and very secret agreement: They would have an open marriage. You know, some would say this wasn’t the best idea.
52. She Almost Divorced Her Husband
In truth, Edwina and Louis’ arrangement was playing a dangerous game. If anyone from the outside world ever found out about it, the British Royal family would be exposed to moral outrage. Louis lived in terror of this exposure, and the possibility of divorce always hung in the background, with the couple reconsidering it several times.
But that was far from their biggest problem...
53. She Had “Extremely Low Morals”
As she reached late middle age, Edwina had completed her transformation into a stalwart symbol of Britain. Yet few knew her biggest secret—and it’s contained in an FBI file. Dating from 1944, the file deems the Mountbattens “persons of extremely low morals.” See, although the affairs of their younger days shocked polite society, there were more dangerous proclivities that they kept locked very, very tight…
54. The FBI Kept Her Secrets
In the government files, there is evidence that both Edwina and Louis Mountbatten were bi—a boudoir taste that was considered utterly depraved for their time. Indeed, there are suggestions that the husband and wife would have threesomes together with their clandestine lovers. Sadly, though, there are much darker allegations.
55. Her Husband Had A Double Life
The final blow of these documents are the harrowing—and infamous—accusations against Edwina’s husband. Although there’s no evidence she was involved, sources now claim that Louis Mountbatten sought out the company of young boys in some of his affairs. It’s a black mark on the scandalous Mountbattens that no amount of today’s progressive morals can erase.
Still, as twisted as their story is, it's almost tame compared to that of Gladys Deacon, who went from socialite to complete recluse...
56. Gladys Deacon Is The Most Disturbing Socialite You’ve Never Heard Of
Gladys Marie Deacon was an American and European socialite and Duchess of Marlborough by way of marriage. Her sensational life story—from a tragic beginning to a fairy tale wedding and nightmarish ending—serves as a cautionary tale for those who get what they wish for. Remember, beauty fades…
57. Tragedy Marred Her Childhood
Deacon's parents had an incredible unhappy marriage—and it all exploded in one twisted incident. Her mother was having an affair with a Frenchman, and her father found out. Enraged, he burst into their hotel room and shot the other man. Mr. Deacon then handed himself into the local authorities. In an ironic twist of fate, revolvers would play a large role in Deacon’s later life as well.
58. She Wanted A Married Man
When Deacon was still a teen, she set her sights on Charles Spencer-Churchill, 9th Duke of Marlborough. There was just one problem. He was already married. Deacon accepted this disappoinment, and actually befriended both him and his wife as she rose through the ranks of society. She even stayed at Blenheim Palace, their home, for a time. Well, the duchess didn't know she had a snake in her midst.
59. She Made A Comeback
At the age of 20, four years after her visit to Blenheim Palace, Deacon would make her return. The Duke of Marlborough invited the most-talked-about socialite in Europe back to his home at Blenheim Palace for a six-month visit. This gave Deacon all of the time she needed to make the Duke fall in love with her. She had a secret weapon on her side, too. See, the Duke and Duchess were in a loveless marriage...
60. She Played The Long Game
Deacon and the Duke's wife, Consuelo Vanderbilt, had become good friends from her first visit to Blenheim Palace—but that didn’t stop Deacon from committing a heartbreaking act of betrayal. While visiting Blenheim Palace the second time, Deacon began what would be a 20-year long affair with the Duke of Marlborough. But she wasn’t about to settle for second place.
61. Her Dreams Came True
Deacon played the role of mistress to the Duke of Marlborough for 20 years. But what she really wanted, ever since she had been a little girl, was to be his wife. In 1921, after two decades of playing second fiddle, Deacon would finally get what she wanted. The Duke divorced his wife and, later that year, married Deacon in style. Sadly, it wasn't exactly happily ever after...
62. She Was Afraid Of The Inevitable
Now that she had everything she wanted; Gladys Deacon just had to keep it. But beauty fades. And she was all too aware of that. Even from a young age, Deacon was terrified that her good looks wouldn’t last. That might be why she worked so hard to get the Duke of Marlborough before everything went awry—and really, considering what happened, awry was an understatement.
63. She Got Wax Surgery
When Deacon heard about a new medical procedure that could make faces take on a "Grecian profile," she jumped at the chance to try it. It involved an injection of paraffin wax into the nose and jawline. Deacon went to France for the procedure before retuning home. Within just a few days, disaster struck. The wax migrated, leaving Deacon horribly disfigured.
64. She Slept With Protection
Gladys Deacon entertained few house guests after her disfigurement. The ones she did entertain, however, left with some particularly sensational gossip. They spoke about her increasingly “erratic” behavior and one…odd habit. Apparently, the Duchess of Marlborough had taken to sleeping with a revolver next to her bed. And the reason was frightening.
65. Her Bedroom Was Off Limits
Gladys’s obsession with her revolver was reminiscent of her father’s earlier actions. But her reasons were a little different. The Duchess kept the revolver within reach, apparently, because she didn’t want her husband to enter her bedroom. Frighteningly enough, the Duke’s first wife had reportedly done the same thing. Clearly, there was no love lost with him, so when Deacon and the Duke separated, no one was surprised. With no man and no desire to leave the house, Deacon spent most of the rest of her years living in total seclusion.
Unsurprisingly, Deacon wasn't the only socialite obsessed with her appearance. And like Deacon, when Rebekah Harkness tried to stop the effect of time, it had disastrous effects...
66. Rebekah Harkness Was The Last Great American Heiress
For a time in the 1950s, socialite Rebekah Harkness was true American royalty. Wealthy, elegant, and beautiful, Harkness seemed to have it all—from her oil baron husband to her notoriously raucous parties. Harkness was the extravagant woman who inspired Taylor Swift's song "the last great american dynasty." But behind her perfect façade lies a chilling history.
67. She Was The Height Of Fashion
Rebekah had always been well-off as a child—as you might guess from the string of nannies who raised her—but marrying William Harkness thrust her into an entirely different tier of high society. By 1956, she had even snagged a photo spread in Vogue, appearing in a neat, black Mainbocher dress with a white satin apron at her back. In a matter of years, her life would go from classy to just plain messy.
68. Her Children Were Tormented
To zero people’s surprise, the Harkness family was utterly dysfunctional. Rebekah’s daughter Edith was clinically depressed and suicidal for much of her life, and spent scores of years in and out of mental institutions following near fatal attempts at self-harm. The most tragic detail? Edith often used her mother’s many, many pills to perform these attempts—and Rebekah was anything but empathetic.
69. She Wanted Her Daughter To Die
Faced with Edith’s grim drive to end her life, Harkness was coldly philosophical. Besides taking pills, the poor girl also jumped off a roof on at least one occasion, and in response, Harkness only mused at her daughter's various attempts. “How should she do it?" She wondered. "Is there a chic way to go?” One day, Rebekah would find out that question for herself.
70. She Took Dangerous Injections
As she aged, Rebekah started to live off of “champagne and injections,” including testosterone and an assortment of pain medications. This had devastating consequences. People reported that Harkness’s lavish marble bathrooms were often splattered with blood, and that her muscles had begun to calcify. The train wreck was now chugging along, and it wouldn't stop until Harkness took her last breath.
71. Nobody Mourned Her
The end came swift, fast, and brutal for Harkness. Though her children Edith and Terry rushed to her bedside, the scene was anything but heart-warming. According to Bobby Scevers, her much younger lover, ''It was complete chaos…everybody running around signing wills and trying on different wigs.'' And when Rebekah actually died on June 17, 1982, things only got weirder from there.
72. She Made Herself A Monument
Harkness had to do everything in style—even when it came to moving on to the next life. Before she passed, the socialite spent $250,000 to commission a bedazzled urn from none other than Salvador Dali. Ironically nicknamed “The Chalice of Life,” the morbid monument stood right at the intersection between tacky and lavish, just like Rebekah herself. And when the time came to put Harkness into the Chalice of Life, the plot thickened.
73. Her End Was Embarrassing
Money can’t buy sense, and apparently Harkness’s designer urn was far too small for her actual remains. As Rebekah’s friend said, “Just a leg is in there, or maybe half of her head, and an arm.'' So instead of giving her mother a dignified end, Rebekah’s daughter Terry had to carry the rest of her ashes home, bound up loosely in a humble supermarket bag. What an unseemly end for the last great American dynasty.
Of course, sometimes the fireworks and drama come just before the end, as was the case with Babe Paley...
74. Babe Paley Was The Queen Of New York
From the time she was in the cradle, Babe Paley’s parents wanted great things for their little girl. Well, she certainly got them—but it came at a heartbreakingly high price. A debutante at 18 years old and a high-society wife at 25, Babe had New York City in the palm of her hand. Yet the bigger they are, the harder they fall.
75. She Had Big Shoes To Fill
Babe’s big sisters Minnie and Betsey soon married into the fabulously wealthy Astor and Roosevelt families, and Babe herself was turning out to be quite the high-class looker. The sibling trio were quickly the talk of the town, and society dubbed them “The Fabulous Cushing Sisters.” Of the three, Babe would be the most famous—and the most tragic.
76. She Was A Trophy Wife
Babe married William S. Paley in July, 1947. Their lavish wedding was the talk of the town, but for all the wrong reasons. The ceremony occurred a mere four days after Bill Paley’s divorce became official, and high society didn't fail to notice the age gap between the newlyweds. Babe was just 32 years old, while Bill was over a decade her senior at 45. However, these weren't even the biggest shadows that hung over the marriage...
77. She Had A Sugar Daddy
Babe and Bill’s courtship had yet another disturbing facet: They were shamelessly using each other. Sure, they might have been in love, but Bill Paley was also a shrewd man who wanted a high society WASP to legitimize his empire. Meanwhile, Babe was looking for a sugar daddy who could take care of her. Their marriage certainly ticked these boxes, but when it came to happiness? Not so much.
78. Her Marriage Bed Was Barren
Babe once confessed to her close friend Truman Capote that she and Bill hadn’t had intimate relations for years. Eventually, it got so bad that they hadn’t slept with each other for an entire decade—and to add insult to injury, it was Bill who spurned Babe. As one confidant admitted, "It wasn't that she denied him. He just lost interest.” Instead, his interest lay somewhere else entirely…
79. Her Husband Cheated On Her Mercilessly
In the dry desert of their marriage, Babe Paley’s husband found an oasis in a bevy of other women—women who could not have been more different than Babe. Bill trawled bars and clubs to pick up models and upcoming starlets, and went to Hollywood on “business” trips that were really for pleasure. And his type? Busty blondes in the vein of Marilyn Monroe. AKA definitely not Babe.
Still, she never said a cross word about her husband, except to her closest confidantes. Well, as we’ll see, her misery had to come out somehow.
80. She Had A Furious Outburst
As Babe’s health declined, she finally got her bitter revenge on Bill. In front of her husband and a room of people, Babe finally dropped the polite façade and unleashed a slew of insults on her spouse. "She complained…that she had done too many things that he wanted her to do," one source recalled. "She knew she was dying. She didn't have anything to lose." As it turned out, though, Bill was about to deal her two final insults.
81. Her Husband Betrayed Her
Even with Babe on her deathbed, Bill was still philandering. Apparently unable to keep his decency in his pants, Bill took up with yet another mistress, Joan, around this time. Even worse, he met his 30-year-old paramour at his granddaughter’s school play, which was a low blow even for Bill. Only, Bill waited to really twist the knife in until the very, very end.
82. She Passed At The Perfect Time
On July 6, just one day after her 63rd birthday, the end finally came for Babe Paley. Despite the tragedies and betrayals that had preceded it, it was an end fitting for the woman who had (almost) everything. Even during her last breaths, the socialite reportedly found the energy to put on a full face of makeup to stare down death. For all this planning, though, her memorial was still steeped in scandal.
83. Her Rivals Tried To Steal Her Man
On the day Babe Paley was buried, her widower Bill Paley seemed to be up to his old tricks again. While Babe’s old friends stood in awe of the floral arrangements and thoughtful touches at her memorial, the photographer overheard a salacious detail. Multiple women at the tables were eyeing up Bill and saying, “I’m going to marry him.”
At least Paley got the chance to tell her philandering husband what she thought of him at the end—because Jackie Kennedy never got the chance...
84. Jackie Kennedy Was A Poor Little Rich Girl
She's now known as Jackie Kennedy and Jackie O, but when she was born, her name was Jacqueline Lee Bouvier. As soon as the baby girl took her first breath on July 28, 1929, she was already part of New York's elite social circle. Her father was the infamous Wall Street stockbroker “Black Jack” Bouvier III and her mother was the socialite Janet Norton Lee.
Despite her well-to-do parents, Jackie quickly learned that money couldn't buy happiness. It just bought great outfits and a metric ton of drama.
85. Her Husband Betrayed Her
Today, JFK’s presidential libido is the stuff of infamy. So how much did Jackie know about her husband’s affairs? According to most biographies, she was basically raised to expect it from her future husband. Men of their “rank” often kept mistresses. Because JFK always returned to Jackie, she accepted his indiscretions. As one source said, “It was a marriage of its time.” But that's not exactly the whole story.
86. She Reached Her Breaking Point
According to an unauthorized biography, Jackie Kennedy wasn’t always so amendable to her husband’s affairs. In this book, the author alleges that Jackie's father-in-law, Joe Kennedy Sr., offered Jackie a whopping $1 million to put up with her husband's constant philandering. If JFK brought home any diseases, that price would jump to a cool $20 million.
But as fraught as this marriage was, things were just as tense between Jackie and her sister, Lee Radziwill...
87. Lee Radziwill Was An American Princess
No one was as worshipped and no one was as doomed as Princess Lee Radziwill. The younger sister of Jackie Kennedy, Lee’s whole life seemed to be a battle with her sibling over who could be more glamorous, more scandalous, and finally, more tragic. Dust off that faded debutante dress for the gripping, heartbreaking story of Lee Radziwill, the American Princess.
88. Sibling Rivalry Was A Problem
Even as a young girl, Lee had to deal with some messed-up Freudian family dynamics. Her older sister Jackie, AKA the woman who would one day become Jackie Kennedy, was her father’s firm favorite, mostly due to the fact she looked exactly like him in her broad cheeks and big eyes. Lee, meanwhile was slender in stature and face—but she still managed to make a formidable opponent for her big sis...
89. She Stole Her Sister’s Thunder
In August 1947, Jackie had her coming-out ball, and Lee found the perfect way to ruin her sister’s moment. Although these well-to-do debutante balls were supposed to be stately, cream-colored affairs, Lee showed up in a loud, pink strapless dress with rhinestones, effectively yanking Jackie’s big day away from her. As Vanity Fair once noted, Lee “loved color, and she loved to be noticed.” When they grew up, their rivalry didn't get much better...
90. She Found A New Man
By her mid-40s, Lee had mostly gotten over her disappointments and romantic upheavals, including a marriage to and divorce from Prince Stanisław Albrecht Radziwiłł. Indeed, she was ready to settle down again, this time with her new fiancé, the West-coast hotelier Newton Cope. Finally, things were looking bright and rosy in Lee’s future—which is how you know it was all about to unravel in a spectacular manner.
91. She Was Afraid Of Her Sister
Although Cope and Lee had a loving, solid companionship, there was one constant issue between them: Lee’s big sister Jackie. The sisters, though emotionally distant, lived near each other, and Cope balked at how much Jackie controlled Lee’s life. He once spat out to her after a dinner party at Jackie’s, “Why the heck are you so afraid of your sister?” Turns out, Lee probably should have been more afraid.
92. She Had A Broken Engagement
Just as Lee was happily planning her wedding to Cope, it came crashing down around her. Practically on the eve of their wedding, Cope called the whole thing off, ending what might have been the society marriage of the year. After all that, what would make a man turn tail and run? Well, Cope’s rumored reason was a doozy.
93. Her Sister Was Conniving
According to Cope himself, Jackie Kennedy Onassis was directly responsible for his broken engagement. As the wedding ramped up, Jackie’s lawyer called the groom-to-be and advised him to sign a whopping prenuptial contract before tying the knot with Lee. The notion immediately disgusted Cope, as did Jackie’s “conniving,” so he dropped Lee like a hot potato. Thanks, sis.
Their sibling rivalry was more like a barely-disguised familial war—but it was nothing like the battle waged between the Countess of Castiglione and her ex...
94. The Countess Of Castiglione Was The World's Meanest Ex
Virginia Oldoini—known better to history as the Countess of Castiglione—was mad, bad, and dangerous to know. The Italian aristocrat’s legendary beauty and photographic misadventures turned her into the world’s first model, but that’s not what made her INfamous. Her bedroom exploits and passionate love affairs gone wrong are what make her story unforgettable.
95. She Was A Child Bride
When Virginia was just 17 years old, her parents wasted no time in marrying her off to Francesco Verasis, the Count of Castiglione. Although the union gave Virginia the name we know her by today, it didn’t give her a whole lot else. The count was 12 years older than the girl, and not much of a looker. But it only got worse.
96. She Stayed In Her Marriage For A Heartbreaking Reason
There was one, and just exactly one, bright spot in Virginia’s marriage to her fuddy-duddy count: Their son together, Giorgio. Oldoini doted on the boy as only a rich mommy can, pouring all her own frustrated hopes and dreams into him. Giorgio, in turn, adored her. Which makes the countess’ infamous act of revenge all the more savage.
97. Her Count Abandoned Her
In 1857, barely a year after the well-heeled couple traveled to Paris, Count Francesco left court for his native Italy in a huff, leaving his young, impressionable wife behind. The separation wasn’t just an idle threat, either. He later scrawled furiously: “Our separation is irrevocable.” As we’ll see later, though, Francesco wasn’t even done yet…
98. Her Husband Tried to Punish Her
Sometime during her separation proceedings, the Countess of Castiglione’s estranged husband decided to ramp up the bitterness and do something truly horrific. He tried to claim custody of their only son Giorgio, using his wife’s lavish lifestyle as proof of her bad mothering. The countess’s response was swift and brutal.
99. She Gave A Cruel Payback
When Francesco tried to claim custody of her only beloved son Giorgio, the Countess of Castiglione didn't take it lying down. Instead, she sent her ex a “present” in the mail. When he opened it, he was horrified. It was a seemingly innocent photograph of the beautiful countess dressed up in a luxurious gown—but when the count looked closer, his blood ran cold.
100. She Threatened Her Ex
Oldoini's photograph was a warning shot to her estranged husband: In the portrait, the well-dressed countess was also holding a knife in her hand, half-hidden in the folds of her dress. The best part? She titled the photo “La Vengeance,” just to make her message extra clear. Wouldn’t you know, she got custody of Giorgio for the rest of his life.