Everybody knows money can't buy happiness, but nobody lived that truth like Gloria Vanderbilt. This "Last Daughter of the Golden Age" started out life eye-poppingly well-to-do, but before the baby heiress was out of diapers, she had experienced unimaginable tragedy. From there, it somehow only got more dramatic—and ten times more scandalous.
1. She Was A Daddy's Girl
Gloria had the definition of a charmed existence—at first. The only child of the fabulously wealthy railroad magnate Reginald Vanderbilt and his second wife Gloria Morgan Vanderbilt, she was the golden apple of her father’s eye. Almost from the beginning, Reginald had a special connection to his daughter. When he first saw his baby girl, he exclaimed, "It is fantastic how Vanderbilt she looks! See the corners of her eyes, how they turn up?"
But little Gloria had precious little time to bask in her father’s love.
2. Her Father Met A Horrible End
Although the Vanderbilt family were already famous for their wealth, class, and taste, they hid very dark secrets behind their gilded doors. For one, her father Reginald was haunted by demons, and his enormous wealth simply wasn't enough to buy his way out of his problems. After a life of drinking, he passed from cirrhosis of the liver when Gloria was only 18 months old.
As the toddler quickly found out, this was just the beginning of her infamous story.
3. Her Mother Took Her Money
With her father's passing, Gloria became a very rich baby—like, she was a millionairess multiple times over. This…wasn’t a good thing. See, Gloria’s mother was only 21 years old, extravagant, and stunningly beautiful to boot. Since the months-old girl was too young to control her estate, her mother took over "responsibility" of the vast sum...with disastrous consequences.
4. She Lost Her Innocence Early
For years, Vanderbilt's mother carted the young girl to and from Paris while she took part in lavish soirees and shopping trips with friends and family. Still, these trips were the opposite of family-friendly. Gloria’s mother often partied with her twin sister, Thelma, who was the illicit mistress of none other than the Prince of Wales at the time, the future King Edward VIII. While she was off having fun, Gloria’s mother forced her daughter into a much different fate.
5. She Loved Her Nanny More Than Her Mother
As a child, Gloria spent very little time with her mother, who apparently had better things to do than raise a daughter. Instead, her Irish nurse "Dodo" came to be the central maternal figure in her life. As Vanderbilt later recalled in her memoir, “Cut by Caesarean section from my mother's womb, I was handed straight into Dodo's arms…Dodo's voice was the first I heard". So it was utterly tragic when her mother decided to punish her using the nanny.
6. Her Mother Betrayed Her
One day, Gloria was in her home when she caught wind of a plot to fire Dodo; as her mother said, “Get rid of the Nurse!” It sent her into a tragic tailspin. She described how it was a “shot to my gut,” and how she suddenly had to face her utter terror of her own mother as she clung to her nanny. In that desperate moment, her whole world changed.
7. She Escaped Her Own Home
Once Dodo understood what Gloria had overheard and that her days were numbered, she gave her some chilling advice: To act completely normal, because they both were going to escape the mansion. She followed through almost immediately, secreting Gloria away and depositing her with her Aunt Gertrude. Gloria didn’t know it then, but it was the start of her destiny.
8. Her Family Started A Huge Feud
See, Aunt Gertrude was one firecracker of a woman, and she was watching the situation develop very closely. The wealthy, well-connected woman finally decided she needed to wrest control of the custody of her niece, and quickly lawyered up to take the rogue branch of her family down. Meanwhile, however, little Gloria was horrendously caught in the middle.
9. She Was In The "Trial Of The Century"
In the blink of an eye, Gloria went from innocence to infamy. People called the ensuing custody battle over the little girl "The Trial of the Century," and boy, did it deliver the goods. The press started digging deeper into the circumstances of Gloria's baby-socialite life, with many focusing on the Vanderbilts' great wealth in contrast to her mother's debauched, irresponsible lifestyle. Some of their discoveries were hair-raising.
10. Her Mother's Secrets Came Out
Although Aunt Gertrude obviously thought something was fishy about her niece's life, even she wasn’t prepared for the dirty laundry that got aired about her family. Members of the press claimed that Gloria’s mother frequently caroused with lovers in the house, and often left compromising photos lying around where young Gloria could surely stumble across them. But that was just the half of it.
11. Her Mother Neglected Her
Sure, maybe the press had it out for the widowed Mrs. Vanderbilt, but even her own mother was against her. Gloria’s maternal grandmother once confessed that “[my] daughter paid absolutely no attention to little Gloria. She devoted herself exclusively to her own pleasures,” and when grandma babysat the girl, “She seldom wrote to me or inquired about the baby". Ouch. And the plot thickens…
12. She Started Drinking Horrifically Young
In addition to all of this risqué behavior, Gloria’s mother even outdid these horrors. During the trial, the lawyers for Aunt Gertrude’s side argued that Mrs. Vanderbilt had taught her young girl to make a whole host of cocktails, since how else was she supposed to entertain her guests? Given all this testimony, the scandalous verdict was a foregone conclusion.
13. She Never Trusted Her Mother Again
Eventually, Gloria’s aunt won the nasty custody battle, but the cruelty wasn’t over. Though Gloria's mother got some visitation rights, the other family members always put her under the utmost suspicion. Furthermore, Gloria’s terror of her mommie dearest only grew, and they drifted apart emotionally. But as it happened, it was out of the frying pan and into the fire.
14. Her Aunt Controlled Her
When Gloria started living with her Aunt Gertrude, it was the opposite of a happy ending. Almost immediately, the budding girl—now about 10 years old—realized she’d traded one monster in for another. Gertrude had stifling control issues and forced Gloria to live under strict rules even in her lavish surroundings. Gloria was now a pressure keg—and she was about to explode.
15. She Had An "Awakening"
As Gloria discovered who she was as her own person, she started pushing her boundaries in a big way. So while she got sent to Miss Porter's prep school in Connecticut, and hobnobbed with alumnae that would include luminaries like Jackie Kennedy, she was no prim society girl. Soon enough, she experienced an intimate awakening—and not with who you might think.
One of her first encounters was with one of her fellow socialites at school…and the details behind the fling were even more scandalous.
16. She Got Intimate In Her Childhood Bedroom
Gloria knew how to look good, but she was a very naughty girl. Her steamy tryst with her school friend happened right under her Aunt Gertrude’s nose, when the two girls were having a sleepover during one of their school breaks. As Vanderbilt remembered, "Truth be told, it was great," she said. "Of course, I didn't quite know what it was, but I didn't want it to stop". The thing is, that’s not even the raciest part.
17. She Had Strange Feelings For Her Nanny
Gloria had every right to explore her sexuality with her friend…but her reasons behind the fling are very uncomfortable. According to the heiress, she first felt the pull of attraction to the unnamed girl because she reminded her of her old beloved maid, Dodo, the woman who had helped Vanderbilt first break away from her mother. Um, well, okay then.
Obviously, dysfunction was starting to appear in Vanderbilt’s perfectly tailored life. It would only get bigger.
18. She Became A Hollywood Hopeful
Gloria went through the underworld and back before she was even a teenager, and it started to show. Constantly restless, she began to dream of leaving high school for Hollywood—and as she grew into an utterly gorgeous young woman, this dream seemed more and more like it could be a reality. So at 17, she dropped everything and went back to live with her mother in Beverly Hills.
Unsurprisingly, Mrs. Vanderbilt wasn't any better at giving her daughter supervision…so this was a very bad idea.
19. She Hooked Up With A Much Older Man
When Vanderbilt moved to Hollywood, she immediately got into massive trouble. At least, that is, in the bedroom. One of the first men she met was the ubiquitous Hollywood producer—and notorious creep—Howard Hughes. At 36 years old, Hughes was almost two decades her senior, but he didn’t mind putting the moves on the naïve teenager fresh from the West coast. And uh, let’s just say Gloria was responsive.
20. She Got Racy In The Bedroom
According to Vanderbilt, she fell into lust with Hughes from almost the first moment she saw him, and when they fell into bed together, she was very grateful for his evident boudoir experience. As she remembered their encounters together, their antics “not only worked, but it was the first time...that summer that I didn't have to fake" her own pleasure.
Unfortunately, if Howard Hughes represents the high of your intimate life, you’re gonna have some big problems. And oh, Gloria did.
21. She Fell In Love With Another Man
Vanderbilt might have felt like hot stuff, but she was still wet behind the ears when it came to love and romance—and she learned that the hard way. In 1941, just after her impulsive teen move to Hollywood and her affair with Howard Hughes, the young Vanderbilt fell in love with Pat DiCicco, another man more than a decade older than her. DiCicco was ostensibly an acting agent, but behind closed doors, the truth was much different.
22. Her Boyfriend Had A Sinister Past
In actuality, the whole “acting agent” thing was mostly just a cover for Pat DiCicco’s real money-making job: He had enough mob connections that he might have even been a "Made Man" himself. Now, you and I read that sentence and think we should take two steps back, but poor, beautiful Gloria Vanderbilt took five steps forward…and paid the price.
23. Her Marriage Was Terrifying
In 1941, almost immediately after meeting DiCicco, Vanderbilt walked down the aisle and married him, becoming his second wife. She stepped into a waking nightmare. The teenager quickly realized that DiCicco was an abusive husband. She later described how when he was in one of his moods, “He would take my head and bang it against the wall". Only, DiCicco didn’t stop at physical threats.
24. Her Husband Called Her Horrific Names
Not content to intimidate his wife through brute force, Pat DiCicco also loved to play mind games with Vanderbilt, emotionally manipulating her. One of his favorite nicknames for his trim teenage bride was “Fatsy Roo". You know, just in case she needed to be taken down a peg instead of given love and affection from someone she trusted. Before long, it all came crashing down.
25. She Escaped Her Relationship
Although Vanderbilt clearly had some daddy issues she was working through, even she realized DiCicco wasn’t worth staying around for. She divorced him in 1945 after just four short years of marriage. Thankfully, they never had any children together—and practically the minute her divorce came through, Vanderbilt was on to her next questionable decision.
26. She Married A Man Old Enough To Be Her Father
Just weeks after officially splitting from DiCicco, Vanderbilt rebounded hard. In April of the same year, she married the talented conductor Leopold Stokowski. Sure, Leopold was in many ways a more stable choice than Pat, but he was also a whopping 42 years Gloria’s senior, and already had three children from his two previous marriages. Oh, Gloria. Why do you think this one is going to work out well?
27. She Was A Society Darling
To be fair, Vanderbilt gave her second marriage the old college try. She and Stokowski were luminaries of the socialite scene wherever they went, and they ended up having two sons together, Leopold “Stan” Stokowski and Christopher Stokowski. However, very few people knew the ugly reality of their marriage, and how desperately unhappy Vanderbilt was underneath.
28. She Turned Into A Kept Woman
Although Leopold Stokowski was far more intellectual than DiCicco and helped Gloria deepen her artistic pursuits, he harmed her in new ways, too. Stokowski was insecure about his beautiful, young wife, and he often tried to keep her all to himself, isolating her and stifling her social life. Vanderbilt, desperate for attention, reacted the only way she knew how.
29. She Had A Fling With A Famous Crooner
As her marriage to Stokowski took a nosedive, Vanderbilt found her escape in none other than Frank Sinatra, engaging in a steamy, secret fling with the legendary crooner. Apparently, this was the wake-up call Gloria needed, and she divorced Stokowski soon after, in 1955. Ah, now’s the time for Gloria to take a step back and try to fix her mistakes…right? Wrong.
30. She Jumped Into Marriage Again
If the definition of insanity is doing the same thing over and over again and expecting different results, Gloria Vanderbilt was certifiable. Soon after her second marriage, Vanderbilt married again, this time to director Sidney Lumet, who won acclaim for films like 12 Angry Men. Although in a welcome change of pace Lumet was the same age as Vanderbilt, many of the same warning signs were there.
Just like Stokowski, he was artistic and demanding. And just like Stokowski, Gloria couldn’t handle him, and they split by 1963. But this is where Gloria got a second wind of notoriety.
31. She Gave Marriage One Last Try
The fourth time was the charm when it came to Gloria Vanderbilt’s love life. In 1963—again, just weeks after her last divorce—Vanderbilt married her fourth and final husband, the dashing screenwriter and actor Wyatt Emory Cooper. Although obviously Gloria’s old habits died hard, this marriage turned out to be one for the ages...and one she could have never predicted.
32. She Met The Love Of Her Life
Vanderbilt wasn’t shy about how much she cared about Cooper; he was firmly the love of her life. Their marriage lasted 15 years and produced two sons, Carter Cooper and the famed news anchor Anderson Cooper. Besides that, they raised Vanderbilt’s two other sons as their own. Vanderbilt confessed, "He made me understand what it would have been like to have had a father—he was a most amazing father".
Her daddy issues finally at peace, Vanderbilt should have sailed off into the sunset with Cooper. Instead, it came to unbelievable heartbreak.
33. She Was In A Power Couple
For an all too brief time, Vanderbilt and her husband seemed to rule whatever room they decided to walk into. They both were extremely good-looking and tasteful, leading them to hit the “Best-Dressed” lists many times over. But one cold winter day in 1978, their high-society dream world came to a crashing halt, and Vanderbilt was never the same.
34. She Lost Her Husband In A Vicious Way
In December 1977, Wyatt Cooper suffered a heart attack at the young age of 50. Though he survived, it sent a shockwave through the entire family, and he scheduled open-heart surgery in the next month. It ended in everyone’s worst nightmare. Cooper never made it out of the operating room; dying the table on January 5, 1978. Vanderbilt mourned him deeply…and in one strangely private way.
35. She Couldn't Get Over Her Loss
In public, Vanderbilt paid tribute to her late husband by never marrying again—quite a feat for a woman who was always jumping from marriage to marriage. But in her personal life, her devotion was even more obvious. Even decades after Wyatt Cooper’s passing, Vanderbilt told friends and family to address her as “Mrs. Cooper". But as we'll see, her tragedy was far from over.
36. She Tried To Become Normal Again
For the next decade, Vanderbilt pursued artistic endeavors like an array of fashion lines, artworks, and various other hobbies that only heiresses can afford. She also sent her son Carter through Princeton, while the baby of the family, Anderson, went to Yale. Yet, as always, all of Vanderbilt’s happiness came with an enormous price tag.
37. She Witnessed An Unbelievable Trauma
In July 22, 1988, Gloria went through the single-worst experience of her life. That day, she and her son Carter, now 23 years old, were at home in their apartment on the 14th floor. Suddenly, Carter walked out onto the high terrace ledge and looked down, ready to jump. Vanderbilt, who had seen her young, emotional son go out, pleaded at him to back away. But it was far too late.
38. She Watched Her Son Jump
Right in front of her eyes, Carter jumped off the ledge to his tragic fate. "I thought the worst thing that had ever happened to me was when I was 9," Vanderbilt said, referring to the custody battle she went through. "But that wasn't the worst. The worst is to lose a child". Even though Carter’s end haunted Vanderbilt for years to come, she reacted in a surprising way.
39. She Never Forgot Her Baby
In the end, Vanderbilt had been through too much trauma to bury it and move one, and near the end of her life, she still insisted on talking about Carter and remembering him, rather than trying to forget him. She told People magazine in 2016 that people “who knew Carter will start to talk about him and then say, ‘Oh, I’m sorry.’ And I say, ‘No, I love to talk about him. More, more, more.’"
40. Her Lawyer Cheated Her
In the 1980s, Vanderbilt suffered through a bizarre turn of events. It came out that her fraudulent lawyer had never paid the IRS on her behalf, and she owed millions. She had to sell two homes to save her skin and took the man to court to get the money back. Somehow, though, it got weirder: A lawyer actually died during the process, and although she eventually won the case, she never recovered the money.
41. She Had A Hidden Side
Vanderbilt was always quite the introvert, despite the public life she was born into. “I am shy in my relationships with most people,” she once said. Perhaps because of the traumas she experienced at such a young age, this introversion actually comes from insecurity. As she said, “I'm terrified of rejection. If someone is interested in me, they must be the first to make the effort".
42. She Liked To Write Smut
Vanderbilt really did do it all—including writing romance novels. Obsession came out in 2009. Vanderbilt claimed that once she decided to write it, the words just "fell on the page". Even so, some of her highbrow friends thought she was going to ruin her reputation, and protested against it. Her response was perfect. Apparently, Vanderbilt had to restrain herself from saying "Oh, goody!" to this.
43. She Started A Lasting Trend
We can pretty much thank Gloria Vanderbilt for one of the biggest trends in fashion history. Always artistic and creative, Vanderbilt eventually dipped her toes into fashion, first with a line of scarves, and then with a line of designer jeans for women, complete with her signature swan logo on the back pocket. At the time, the idea of high-class jeans was almost unheard of.
44. She Was On Social Media
Late in life, Vanderbilt's son Anderson Cooper talked his 95-year-old mother into getting an Instagram account. She quickly amassed over 200,000 followers. “I have such fun deciding what I am going to post,” she once said of the pastime. “Of course, I am tempted to post all day long, but Anderson warned me I shouldn’t get carried away".
45. She Inspired A Famous Character
Do you like Audrey Hepburn in Breakfast at Tiffany's? Well, you might have Vanderbilt to thank. Some speculate that Truman Capote's character Holly Golightly in the original novel was based on none other than Vanderbilt herself.
46. She Refused To Talk About Her Mother
Vanderbilt had a big interest in dreams, and even went to see a dream analyst starting in her late 20s. However, there was one topic she would never discuss: Her mother. She eventually did, but it took a long time for Vanderbilt to build trust with the man and finally open up. As Vanderbilt said, “About two years later, her name came up". Still, that didn’t mean that Gloria didn't hold grudges.
47. She Cut Her Mother Off
Gloria mother exploited her daughter's trust fund to live out her own sordid fantasies, but when Gloria finally grew up, she got the last laugh—and she dealt her mother an absolutely ice-cold betrayal. As soon as she came of age and got full control of her trust fund, she actually cut her mother off entirely, forcing her to fend for herself. That wasn't quite the end of their story, though.
48. She Had A Difficult Reunion
After cutting her mother off for most of her adult life, Gloria did have a reconciliation with the woman who gave birth to her. After all, as Vanderbilt noted bittersweetly, her mother, “was certainly the most influential person in my life". Age also gave Vanderbilt some perspective on what her mother had gone through. She admitted that her mother was just "this gentle person, who was unable to cope. She really couldn't".
49. She Was Buried Beside Her Beloved
On Monday, June 17, 2019, Gloria Vanderbilt passed in her Manhattan home at the ripe old age of 95. Doctors diagnosed Vanderbilt with stomach cancer earlier in the month, and she only had time to say goodbye to those she loved most dearly. She is now beside her son Carter and her fourth husband Wyatt Cooper, in the Vanderbilt Family Cemetery on Staten Island.
50. She Gave Her Son No Inheritance
There’s no doubt that Gloria Vanderbilt passed with a hefty sum in her pocket. But a huge shock still comes with this money. Believe it or not, none of it will go to her son Anderson Cooper, at least in the form of cash. As he said, “My mom's made clear to me that there's no trust fund". Even so, as Cooper is a millionaire in his own right, we doubt he needs it.
51. She Loved Her Family
On a heart-rending CNN memorial to his late mother, Anderson Cooper gave a tear-filled speech about what Vanderbilt meant to both him and the world. As he said, “The last few weeks, every time I kissed her goodbye, I would say, ‘I love you, Mom. She would look at me and say, ‘I love you, too. You know that.’ And she was right. I did know that".
He also added at the end of his informal eulogy, “What an extraordinary life. What an extraordinary mom. And what an incredible woman".
52. A Maid Blew Her Custody Case Open
There were some details from Gloria's custody battle as a child that are still etched in public memory. First among them was a maid's explosive accusations. Maria Caillot, a Parisian maid, accused Gloria's mother of being in a lesbian relationship with a Lady Nada Milford Haven. The maid claimed she had caught the pair in bed together, making love. The courtroom went eerily silent—and then chaos broke loose.
53. The Court Blew Up
The courtroom went from silent to the very opposite. In fact, no one could hear anyone speak. The story about the lesbian relationship caused the court to erupt in a din of disapproval, and the judge was at a loss. How could he continue? He couldn’t even hear the witnesses. He sent the public out, and from then on it was a closed courtroom. But even then, sometimes the judge needed even more secrecy.
54. She Had Secret Meetings With A Judge
Little Gloria's custody trial was so sensitive that the judge frequently forced everyone to exit the room. This was so she could give her testimony without family members pressuring her. In these closed-door meetings, bystanders frequently heard wailing and crying coming from inside the courtroom—and even though these were private sessions, the press got ahold of one tragic detail.
In one such communique, little Gloria apparently admitted to the judge that she was lonely when she was with her mother, and that she wished she could go live with her aunt instead.
55. Her Aunt Forced Her Hand
This vulnerable admission was very likely what won the custody battle for Gloria's Aunt Gertrude over her mother. Nonetheless, that doesn't mean it was justice for the little girl. When she looked back on this painful time in her life, Gloria Vanderbilt made a heartbreaking confession: She had memories of her aunt actually coaching her on the testimony.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19
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