Beautiful, hedonistic, and wild, Kiki Preston wasn’t your average American socialite. A member of the infamous Happy Valley set, she cultivated her own personal brand of controversial fun. Unfortunately, the thrill didn’t last. As the party-girl extraordinaire became increasingly consumed by substance misuse, dark affairs, and perpetual tragedy, her life plunged into such a chaotic downward spiral that it’s really no surprise she met with such a heartbreaking end.
1. She Was Just Your Average Girl
Before she achieved notoriety as an overindulgent American socialite, Kiki Preston was just a regular New York girl…well, sort of. Born Alice Gwynne in 1898 in Hempstead, New York, Kiki was the daughter of Helen Steele and Edward Erskine Gwynne Sr. Oh, and the Gwynne’s were fairly well-to-do because they were basically akin to American royalty…
2. She Had Ritzy Relatives
Ever heard of the Vanderbilts? Well, Kiki’s father was the nephew of famous railroad gazillionaires Cornelius Vanderbilt and Alice Gwynne Vanderbilt—AKA Kiki’s namesake. Moreover, Kiki’s mother came from an important family herself, having descended from a signatory of the United States Declaration of Independence, Justice Samuel Chase.
In other words: Kiki lucked into a super privileged family with a lot of affluent connections. Still, they say money doesn’t buy happiness…
3. Her Early Years Were Tense
While it might sound amazing to grow up surrounded by wealthy relatives, Kiki’s childhood was filled with utter misery. Her parents really didn’t get along and had a turbulent marriage, eventually splitting only to reconcile once more. Sadly, the instability of her parent’s stormy union made a lasting impression on Kiki.
You see, kids sometimes grow into their parents, and in Kiki’s case, her hedonistic ways likely came from her father’s side of things.
4. Her Father Squandered Money
Kiki’s father, Edward, was a socialite through and through, albeit an unemployed one. Regarded as a man who “had extravagant tastes, expended money lavishly and was without business employment,” Edward loved all the pomp and finery that came with living the high life. Unfortunately, his extravagant spending soon led to near-ruinous consequences for Kiki’s family.
5. Her Family’s Well Ran Dry
To the surprise of no one, Kiki’s family’s financial situation soon began to crumble in 1899. So, to offset the problem, her father secured a loan worth several thousand from a Parisian jeweler, and everything seemed to go back to normal. That is, until Kiki’s father did something very strange. After securing the financing, Kiki’s father immediately handed off the interest in his property to his mother, Louise Gwynne—thereby signaling his possible inability to repay the jeweler. Oh, Eddie…
Naturally, the moneylender found out and immediately sensed a con...
6. Her Family Landed In Hot Water
Fearing that Kiki’s father duped him, the moneylender promptly filed suit against the Gwynnes for an outstanding debt of about $50,000 for diamonds. Yep, diamonds. Then, to further complicate matters, Kiki’s grandmother unexpectedly died—and the unpleasant surprises only continued. It turned out that old Grams named Kiki and her siblings as her beneficiaries instead of Edward.
This meant that, with the family property now held in trust, there was no way for Kiki’s father to reclaim his assets. Oops. Her family was now in deep financial trouble…
7. She Was Destitute
Unfortunately, you can’t get blood from a stone, and Kiki’s father couldn’t cough up the cash he owed. Desperate, Kiki’s family had no choice: They declared bankruptcy the following year, with nearly $56,000 in liabilities and just $57 in assets. Financially, they had nothing left. Then, somehow, things got even worse for Kiki…
8. She Endured Another Tragedy
Getting caught up in a tumultuous family situation coupled with financial problems was bad enough for a kid—but that was just the start of Kiki’s nightmare. When she was just five years old, her father suddenly died from acute kidney issues at the ripe old age of 35. Ironically, Edward died on the same day the suit’s court hearings were supposed to begin.
But, of course, that didn’t mean that the Gwynne family’s financial woes magically went with him, heck no. Kiki’s inheritance was about to fall into jeopardy…
9. Her Inheritance Was On The Line
Though she was still just a child, Kiki and her siblings suddenly found themselves bearing the burden of their father’s financial mismanagement when, four years after Edward died, the furious moneylender resumed seeking compensation for the loan. Remember, her family only had one valuable asset left—the property held in trust for Kiki and her brothers—and the moneylender was now demanding it in lieu of the money.
Meaning there was now a strong chance that Kiki would soon have nothing left but the clothes on her back…
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10. She Kept Her Home
Fortunately for Kiki, that didn’t happen. By some minor miracle, the judge dismissed the complaint after deciding that Edward had never truly intended to swindle his creditors—he was just thoughtless. So much so, in fact, that the judge spoke quite badly about Kiki’s departed father, describing him as a guy who “may have had large expectancies, but seems to have been a drain upon his mother’s financial resources.” Ouch.
Regardless, Kiki and her family were at last free of their financial woes. Yet, remarkably, Kiki didn’t seem to learn from her father’s mistakes.
11. She Returned To A Posh Lifestyle
Having just narrowly avoided complete and utter ruin, Kiki threw caution to the wind and began living her best life. Though she periodically visited her family residence in New York, she lived primarily in Paris. She also obtained a fancy education in England, because why not? Still, it wasn’t enough: Something inside her began to itch. Life seemed dull and Kiki, like her father, yearned for something…more.
Unfortunately, she began looking in all the wrong places.
12. She Embraced Her Joie De Vivre
Kiki craved a life of intrigue and excitement, and she wasn’t shy about it either. So, what’s a bored American socialite to do? Well, apparently, her solution was to turn to the stage—by performing in the cabaret. To Kiki, her stint in the spotlight was probably little more than a harmless diversion; but in reality, it was just the tip of the iceberg of her much wilder, bon vivant nature.
Kiki’s life was all about fun and games. Unfortunately, the good times soon turned bad…
13. She Lost Another Family Member
Seemingly out of the blue, Kiki’s brother, Edward C. Gwynne, died unexpectedly. Her brother was a member of the United States Army Air Corps, and he met a tragic end when his plane brutally got shot down. This now marked Kiki’s third loss; her family members were dropping like flies at every turn. Knowing that life was fragile, Kiki opted to seize the day…
14. She Found Romance
Before long, Kiki fell in love. She married Horace R. Bigelow Allen in 1919 as soon as he finished his service in the United States Army, and together they had two kids: a son, Ethan Allen, and a daughter, Alice Gwynne Allen. On the surface, they seemed like the perfect family—but behind closed doors, something nagged at Kiki. Where was the fun? Surely, life could be far more exciting than this?
Little did Kiki realize—she was about to meet a unique and colorful duo who would soon change everything.
15. She Made Some Interesting Friends
So, who exactly were these strange new people? Well, Kiki met and befriended Alice de Janzé and Josslyn Hay, the 22nd Earl of Erroll. They, like Kiki, were both future members of the Happy Valley set, a notoriously hedonistic group of elites known for their love of illicit substances, booze, and promiscuity-fueled hijinks…among many, many other things. In fact, this group’s escapades would one day become so scandalous that they’d all later go down in infamy.
Naturally, Kiki fit right in with them; she was desperate to embrace her darker side. So, like a moth to a flame, the thrill-seeking socialite eagerly adopted their “lifestyle.” However, it wasn’t long before she got burned...
16. Her Marriage Crumbled
It’s difficult to say what ultimately caused their split, but it’s hardly outside the realm of possibility that the debaucheries of the Happy Valley set weren’t to Horace’s tastes. What’s not in dispute, though, is that he ultimately left Kiki, causing her to file for divorce on the grounds of desertion in November 1924.
But, abandoned or not, Kiki barely even seemed to notice he was gone…
17. She Found A New Husband
Kiki swiftly moved on to another man who was apparently okay with her latest proclivities. Just five months after her divorce, Kiki married Jerome “Gerry” Preston, an investment banker, in April 1925. Writer Frédéric de Janzé characterized Kiki’s new beau in his memoirs as “untamed,” among other words, which I’ll assume was just his polite way of saying: This dude was crazy.
But Gerry soon found that he had competition, as he wasn’t Kiki’s only close relationship...
18. She Formed Another Curiously Close Bond
While in Europe, Kiki established a fleeting yet intriguingly deep friendship with Kay Francis, an American stage and cinema actress. Though they’d actually met several times over the years, their relationship rose to a whole other level after Kiki married Gerry. Indeed, the two ladies spent the entire summer together, going on dinner dates, having long, intimate chats, and taking extended drives alone through the French countryside. Ooh la la.
Kiki’s relationship with Kay reached its pinnacle in the fall…
19. Her Relationship Grew More Intense
Though Kay was technically in France to divorce her husband at the time, she was also simultaneously juggling several men on the side. Still, Kay always managed to make time for Kiki (aw, how sweet). Then finally, on September 13, 1925, they took their relationship to the next level. After one particular lunch, Kiki and Kay decided to spend the night together at Kiki’s apartment, an experience which Kay referred to as “Very nice!” Kiki was on cloud nine.
But alas, their romance didn’t last…
20. She Said Goodbye
Following their night together, Kiki spent the next few days with Kay until, inevitably, Kay had to return to New York. The two ladies dined together one final time on September 16 before Kay departed, leaving behind a very dejected Kiki. Unfortunately, the pair all but lost touch afterward, going entire years without ever seeing each other. As a result, their friendship never recovered.
It was around this time that Kiki decided to quit Europe for good…
21. She Relocated To Africa
While traveling with the Happy Valley set, Kiki’s new friends encouraged her and her husband to permanently relocate to Kenya, which at the time was the British East African colony that the group was now calling “home.” The idea appealed to Kiki—after all, she craved adventure! So, when a friend offered her some land on the banks of Lake Naivasha, Kiki leaped at the chance. How could she possibly say no?
Kiki excitedly settled into her new life…
22. She Reinvented Herself
Kiki and her husband built a Dutch-style house on the shores of Lake Naivasha where, interestingly, our born-and-bred city girl began devoting larges chunks of her time to running a farm, where she bred horses and hunted large game. Of course, the Happy Valley set also became an inextricable part of her life as well, and not necessarily for the better…
23. She Partied Way Too Hard
Though she often entertained and associated with an invariable who’s-who of viceful notables (like the turbulent Alice de Janzé, the Earl of Erroll, and his wife, Lady Idina Sackville), Kiki herself became somewhat of a controversial figure—even among the Happy Valley set. In fact, it wasn’t long before the attractive socialite’s wild lifestyle began to raise eyebrows, especially given her propensity for partying all night long and then sleeping in until dinnertime.
She was party-hardy, to be sure. But that wasn’t even the worst part…
24. She Became A Full-Fledged Junkie
Dangerously, Kiki’s substance use soon spiraled out of control to an alarming degree. She became completely hooked on a number of illicit substances and developed the awful habit of carrying a syringe with her wherever she went, thus earning her the nickname “the girl with the silver syringe.” I mean, you’d think by this point that someone would have intervened with her here, but sadly, nope.
25. Her “Habit” Became A Source Of Bemusement
Sickeningly, Kiki kinda received the exact opposite of an intervention: Her “friends” got a kick out of her substance misuse. You see, Kiki had grown so reliant on her needle that she started pulling it out at random to inject herself, regardless of where she was or who she was with at the time. She’d do it instinctively, entirely oblivious to spectators, and no one would say a thing. At least, not to her face, anyway…
26. People Mocked Her Behind Her Back
After witnessing Kiki freely inject herself without making so much as an attempt to hide it, a woman by the name of Cockie, who was the second wife of Swedish Baron Bror von Blixen-Finecke (say that 10 times fast), once sarcastically quipped: “She’s very clever with her needle.” No doubt that comment got met with all sorts of derisive laughter.
Obviously, with no one intent on getting Kiki any help, her addiction came at a tremendous cost—both figuratively and literally.
27. Her Dependency Was Sky High
Frank Greswolde Williams, the Kenya colony’s primary dealer, lived in the Kedong Valley, not far from where Kiki lived by Lake Naivasha. Still, illicit substances are expensive, and maintaining her supply must have cost Kiki a small fortune throughout the years—especially given that she insisted on hiring a private plane to pick up and deliver her “goods” on a regular basis... Because, you know, everyone has a private plane at their disposal.
Honestly, even just imagining the cost of that gives me major anxiety. Though, it’s possible that she wasn’t funding it alone…
28. Monogamy Was Not Her Thing
Okay, no judgments here; to each their own. While Kiki was technically still married, she had a constant wandering eye. To put it mildly, she took multiple extramarital lovers over the years, including actor Rudolph Valentino—AKA “The Latin Lover.” But one relationship, in particular, was especially risky.
29. She Had A Royal Affair
Kiki certainly had her fair share of wild affairs throughout the years, but none were nearly as audacious as her fling with a certain English royal. Like Kiki, Prince George, the Duke of Kent, was a bit of a wild child himself, so it goes without saying that upon meeting in the mid-1920s, they found they had a lot in common and became fast friends.
However, that friendship quickly evolved into passion…
30. She Got Freaky With The Prince
Sure enough, Kiki and Prince George became lovers—and behind bedroom doors, their affair was as outrageous as it gets. At this point in their lives, both Kiki and the prince had considerable experience in the bedroom, and they were eager to...ahem, try new things. So much so that according to reports, Kiki and Prince George had a ménage à trois with Jorge Ferrara, the bisexual son of Argentina’s ambassador to London.
But as daring as Kiki was, she soon took things a step too far…
31. She Was A Bad Influence
Kiki being Kiki, she didn’t exactly restrict her activities with the prince to the bedroom, if you catch my drift. Before long, Kiki had Prince George hooked on multiple drugs, most notably morphine. Uh-oh. Regardless, the prince still greatly cared for Kiki, and he had absolutely no intentions of distancing himself away from her.
Of course, this didn’t exactly go over very well with the royal family…
32. The Royal Family Hated Her
Now, to be fair, Prince George was no great saint before Kiki met him, so it wouldn’t be entirely fair to say that Kiki was solely to blame for “corrupting” him. Nonetheless, Kiki had a bad rep, and his associations with her greatly upset the other royals—especially Prince George’s older brother, Prince Edward. In his mind, there was no other option: Kiki had to go.
33. Her Relationship Was Tested
Believing that Prince George would never get sober with Kiki still hanging around, Prince Edward grew increasingly desperate to free his little brother from Kiki’s drug-dispensing claws. He tried diplomacy at first, pleading with the toxic pair to end their relationship, but no dice. So, when talking failed, Edward came up with a plan to get his brother away from Kiki.
34. She Got Booted From England
Eventually, Edward successfully broke off George’s relationship with Kiki, but it wasn’t easy. In the end, Prince Edward only managed to separate the two addicts by literally forcing Kiki to leave England during a visit in 1929. Even so, Edward continued to worry for years thereafter that his brother might fall back into addiction if he ever saw Kiki again.
Sure enough, his fears were nearly realized a few years later…
35. She Met Him Again
Kiki unexpectedly stumbled into Prince George once again in Cannes in 1932. But to everyone’s utter chagrin, Kiki wasn’t about to go quietly this time. She refused to leave despite being asked to do so. A tense confrontation quickly ensued, ending only with Kiki getting near-forcibly dragged away from her former lover. It was a low point for Kiki, to be sure.
As it turned out, though, addiction may not have been the only factor in the royal family’s concerns regarding Prince George’s relationship with Kiki...
36. She Got Caught In A Rumor
Already, there was a lot of gossip surrounding Kiki and George, which the royal family probably didn’t like. But the most intriguing rumor of them all was outright scandalous. Allegedly, they had a secret son together. According to the memoirs of Loelia, the Duchess of Westminster, Prince George’s brother believed that a boy named Michael Temple Canfield, the adopted son of American publisher Cass Canfield (and one-time brother-in-law of Jackie Kennedy Onassis), was actually Kiki’s and Prince George’s secret lovechild. Whaaat…
But it couldn’t possibly be true…Could it?
37. The Gossip About Her Was False
As it turned out, no. Fortunately for Kiki, the boy’s birth mother was later revealed to be the daughter of a Canadian coal merchant, Violet Isobel Christine Evans. Still, you can understand how such a crazy rumor would have utterly blown people’s minds at the time, and that’s not even to mention the backlash that likely would have fallen squarely Kiki.
But, vindicated or not, it almost didn’t matter: Kiki was still about to experience the worst time of her life…
38. She Nearly Lost Another Family Member
Having already lost her grandmother, father, and brother, it’d be fair to guess that Kiki lived in constant fear of “the phone call.” Then, one day, it came. In May 1929, she learned that her sole surviving brother, Edward Erskine Jr., had suffered a heart attack and was barely hanging on. Believing him to be on the verge of passing, a distraught Kiki flew back to Paris to be by his side.
Miraculously, her brother survived...but this wouldn’t be her only scare.
39. Her Next Few Years Were Turbulent
The near-loss of her brother was only just the beginning. The 1930s and 1940s were unfathomably awful for Kiki as she began to lose nearly everyone she’d ever held dear. Unfortunately, as Kiki slowly suffered through those devastating losses, the weight of her grief would wreak absolute havoc on her mental well-being…to the point where she’d eventually break.
40. She Lost Her Cousin
The first of her loved ones to go was her cousin, William Kissam Vanderbilt III. The 26-year-old was driving home from his father’s mansion in Florida when he abruptly lost his life in a car crash on November 16, 1933, in South Carolina. Though Kiki’s brother, Edward Erskine Jr., was also in the car with him at the time, he somehow managed to walk away with only minor injuries. Sadly, he’d later experience paralysis as a result of yet another collision that occurred two years later.
As saddened as she was by the sudden passing of her cousin, Kiki next experienced the worst loss of her life (thus far) only six months later…
41. Her Husband Died
Shockingly, Kiki became a widow at 36 years old when her husband, Gerry, abruptly died from pneumonia on May 28, 1934. He’d only been in New York for a week when his sickness unexpectedly got the better of him. He perished at the age of 37 while staying at the Hotel Pierre. Fortunately, Kiki was with him at the time. Though given the circumstances, this was probably of little consolation to her.
Then, roughly three years later, Kiki was forced to all but relive her husband’s passing via her brother-in-law…
42. She Lost Her Brother-In-Law
Believe it or not, the next unfortunate soul in Kiki’s life to kick the bucket was Gerry’s younger brother, Lewis Thompson Preston, in February 1937. Eerily, Lewis also died at the age of 37—the same age as Kiki’s husband, which honestly must have been incredibly emotionally triggering for Kiki. Oh, and not to sound insensitive or anything, but speaking of “triggers…”
43. Her Friend Became A Homicide Victim
Kiki’s old friend and Happy Valley buddy, 39-year-old Josslyn Victor Hay, the 22nd Earl of Erroll, was discovered shot in his car in Kenya on January 25, 1941. That news must have been horrifying enough for Kiki to hear, but to make matters even worse, one of the top suspects was none other than Kiki’s other longtime close friend...
44. Her Best Friend Stood Accused
With no witnesses to the shocking slaying of the earl, suspicion quickly fell on another of Kiki’s dearest friends, Alice de Janzé. Although she supposedly had an alibi, Alice, unfortunately, had a sordid history that quickly made her a top suspect within the Happy Valley community: drugs, romantic ties to the earl, and, oh yeah, an earlier attempt to knock off a former lover. Woefully, it all became too much for Alice.
Later that same year, she took her own life on September 30, 1941. The depth of Kiki’s heartbreak must have been unimaginable by this point. Still, the hits kept on coming…
45. Her Former Lover Had An Accident
Unbelievably, barely a year after losing Alice and the earl, Kiki’s beloved Prince George lost his life in a tragic plane accident at the age of 39. Still, the fates weren’t done persecuting Kiki yet, oh no. Rather cruelly, the universe saved Kiki’s most painful loss for last. In fact, there’s little doubt that this final round of devastating news brought Kiki to her knees...
46. Her Son Gave His Life
By this time, WWII was in full swing, and as we all know, the casualty rates were enormously high. But one life, in particular, was especially precious to Kiki: Ethan Allen. Sadly, Kiki’s son perished in the Normandy Landings on June 6, 1944, while bravely serving with the Royal Canadian Air Force. Her son’s selfless sacrifice brought an end to the lengthy string of heartbreaking tragedies in Kiki’s life. Still, his devastating loss seemed to be the final straw for his mother: Kiki finally snapped.
47. Her Mental Health Suffered
Understandably, Kiki began to fall apart. She’d lost so many loved ones by now that it was hard to keep track. The losses, the shocks, the constant heartache…Kiki soon found herself struggling to cope with it all. Utterly shattered, she began suffering from mental health issues, which probably wasn’t at all helped by her constant substance use. In any case, her fragility began to show…
48. She Fell Ill
Kiki fell into incredibly poor health. According to Kiki’s friend, Lillian Turner, Kiki spent her final days in a heartwrenching state of depression and anxiety. While attempting to help care for her, Lillian recalled handing Kiki a glass of milk before heading off to the living room to read. But a short while later, Lillian realized that something was terribly wrong…
49. She Made A Rash Decision
The apartment seemed too quiet. Not hearing any noise coming from Kiki’s room, Lillian stopped reading and got up to check on her. But when she opened Kiki’s bedroom door, what she saw next made her blood run cold. The bedroom window of Kiki’s fifth-floor apartment was wide open. Kiki, sadly, was nowhere to be found.
50. She Took Her Own Life
Dressed in her pajamas, Kiki Preston jumped out her apartment window at the Stanhope Hotel in New York City on December 23, 1946. She was 48 years old. Even more tragically, Kiki’s body landed in the courtyard…and her mother, Helen Steele, resided in that same hotel at the time of her daughter’s passing.