Pamela Harriman was a wealthy country girl with big dreams. During a time when women only dreamed of equal opportunity, Pamela used her refined manners and seductive prowess to woo powerful men in high places. Her ambition was tantamount, and by entertaining romances with famous men, she climbed her way to the very top. She was, in every way, both a masterful businesswoman and a bewitching lover.
1. She Had Humble Beginnings
Pamela Harriman, born Pamela Digby, entered the world on March 20, 1920. Her parents, Edward and Constance, laid their firstborn to rest in an interesting crib—the bottom drawer of a wooden chest. But this simple bedding was but a cozy substitute for the bright nursery that awaited her at Minterne Magna, a large manor and property that promised nothing but a delightful childhood.
Whatever her humble beginnings, Pamela had a larger-than-life path ahead of her.
2. She Was On Her Own
Pamela Harriman got her first taste of travel when she was only 18 months old. Her parents uprooted the entire family and moved to Australia—a land of better tax advantages and exotic fauna. But there was a dark side to it all. In truth, her parents wanted very little to do with their daughter—it was the English way, after all. She made the trip to Australia on a boat with her nanny, completely separate from her parents.
This disconnect paved the way for Pamela’s independent and rebellious nature and made for some interesting milestones along the way.
3. She Had Interesting Tutors
Pamela Harriman learned her first words, not from doting parents, but rather...from a doting parrot. Yes, a chatty white pet parrot taught her to speak, but also instilled in her a love for mimicry that she later used to emulate accents such as Winston Churchill’s. She also learned to ride horses at the tender age of three.
But instead of being taught by her own father, it was the Ashton brothers—her father’s polo-playing friends—who were her main tutors. This passion for horse riding followed her throughout her life.
4. She Jumped Hurdles
By 1924, the Digby family had settled back into their large family home at Minterne, enjoying every comfort of an upper-class existence. It was here, on 1,400 acres of land and countryside, that Pamela had the freedom to hone her talents on horseback and eventually took her riding to the competitive level, performing confidently in shows at the International Olympia.
But despite her idyllic and pampered upbringing, Pamela couldn’t help but feel trapped by the isolation of her home life. She felt destined for something more.
5. She Had No Real Friends
Pamela was undeniably a people person and she hated being alone. This made her all the more resentful of her life at Minterne, where her only real friend was her sister Sheila, if she could even consider Sheila a friend. The two girls barely got along and to Pamela, her sister was the farthest thing from the fun-loving people she wished to surround herself with. The two of them were opposites in every way.
6. She Dreamt Of Escape
Pamela was ambitious and extroverted—she sought the spotlight and thrived in its glow. Unlike her sister, Sheila enjoyed solitude and took to hunting alone in the forest, something Pamela abhorred. At the end of the day, it was Pamela who thought nothing but of escape. To her, the country was mundane and mind-numbingly boring.
She dreamed of the city’s diversions and the company of fascinating people. She wanted to learn, not from the dusty pages of books, but from experience.
7. She Felt Unaccomplished
In 1934, after years of pleading to be sent away to school, the Digbys sent both Pamela and Sheila to a boarding school in Hertfordshire called Downham. After two years studying home economics, she jetted off to Paris for study at a finishing school. Later in her life, Pamela used her time at these institutions to concoct an elaborate lie.
It was one that stretched the truth to better serve her image. She wanted to seem more accomplished than she actually was.
8. She Was A Liar
As an adult, Pamela embellished her educational accomplishments, effectively lying about her qualifications to hide her embarrassment over her meager academics. She called Downham a college and claimed the ‘B’ she received stood for bachelor, hoping that her peers would believe her to be a college graduate. And then there was the Paris finishing school.
She referred to her time there as “post-graduate work at the Sorbonne”—but in fact, there was no record of her ever receiving a degree or diploma. According to a friend—"With Pamela, it’s always hard to find where the truth lies".
9. She Was Still A Country Girl
When Pamela arrived in Paris, she was still a naive and pampered country girl—bright-eyed, with a head covered in bouncing, red curls. Sheltered by her nannies, she was still more a child than a modern teenager and had difficulty adjusting to the bustle of city life. In addition, she was also completely uneducated when it came to manners of the heart.
With a chaperone attached to her at the hip, there was no possibility for her to meet an eligible young man...but Pamela knew what she wanted, and it was only a matter of time until she got it.
10. She Went In Blind
After Paris, Pamela moved to Munich—but her timing? Not so great. At that point, Munich was the beating heart of Nazi Germany. In 1938, the city served as headquarters for Hitler’s Nationalist Social Party and there were already outward displays of unrest. But Pamela, unphased by the presence of infantrymen in her new city, wasn’t completely anti-German.
In fact, like many others, she hoped to one day meet the Fuhrer in the flesh. Be careful what you wish for…
11. She Met Him
According to Pamela, a mutual friend named Unity Mitford arranged a tête-à-tête between her and the German leader. They met one afternoon over tea at Munich’s Englischer Garten—just a casual cup of tea between a teenage girl and The Fuhrer. But oddly enough, this meeting didn’t make as dramatic an impression on Pamela as one would believe.
In later interviews, her descriptions of this momentous day were surprisingly vague and her account of the Fuhrer's character conveniently cliché. Once again, there was evidence to suspect her honesty...did this meeting even take place?
12. She Built Her Image
Pamela’s interesting anecdote about her meeting no doubt amped up her image later in life when she became more politically active. And while onlookers took her word for it, her inability to name specifics about the dates, times, and happenings can’t help but seem curiously suspicious. Even one of her closest friends—Sarah Baring—had her doubts, saying “Hitler didn’t entertain [British girls] that way".
And so, Pamela’s time in Munich remains somewhat of a mystery.
13. She Put The Pedal To The Metal
It all began with a green Jaguar, or rather, Pamela’s freedom began with a green Jaguar. In the summer of 1938, she returned to Britain from Europe where the isolation of country living threatened to pin her down once again. A generous gift of a sports car on her 19th birthday ensured that she had free reign to leave Minterne on weekends to pursue gregarious pastimes in London and Leeds.
But of course, this was not exactly what her parents had in mind.
14. She Was Outrageous
If Pamela’s parents thought her rebellious phase had already happened, they were dead wrong. It was just starting. She was completely apathetic to her parent’s concerns. In this way, she took after her great-great-aunt Jane Digby—a courtesan with a penchant for travel, adventure, and seduction. It turned out Pamela was quite the same. She wanted nothing but her independence and owned her beauty.
When she was out on the town, she was a total flirt. In fact, she proudly flaunted her high heels and ample bottom. Bored with the boys her own age, Pamela used her freedom to woo older men—a pursuit that was more than she bargained for.
15. She Fancied Older Men
In 1939, Pamela met a dashing and very rich divorcé named Fulke Warwick. He was 11 years older than her and already had a son. Around this time, Pamela had quite the knack for disappearing and then reappearing, going wherever she wanted when she wanted to. So, it wasn’t much of a surprise that when she disappeared from Leeds castle one weekend. Nobody knew where she had gone.
But of course, when Monday rolled around, the whole sordid story came spilling out.
16. She Disappeared
On the Monday after her disappearance, Pamela promptly returned to Leeds castle, claiming that she had jetted off to Paris with none other than Fulke Warwick. Although they kept separate lodgings, they still spent much of their time together, having fun and dancing into the night. He even gifted her an expensive pair of jade earrings.
Despite this intimacy, nothing truly untoward transpired. That is, they never actually slept together. But no matter the claims of innocence, Pamela’s reputation still hung in the balance.
17. She Couldn’t Care Less
Of course, Pamela didn’t care what others whispered about her. All she cared about was having a good time. Fulke Warwick, on the other hand, cared enough for both of them, and, worried about his own reputation, broke off their brief but memorable fling. But this pleasurable excursion to Paris was just the beginning for Pamela. She had already proved herself reckless and ambitious.
As she set her aims high, she never again gave men her own age a second glance...
18. She Bet It All
It wasn’t all about flirting for Pamela. Her rash behavior also manifested in her gambling, and somehow, no matter the result, she always managed to get her way. One summer she lost a whopping 100 pounds at the track—an equivalent to half a year of her allowance. Instead of having to deal with this blow, she ran to her father, demanding he replace the money she’d lost.
Similarly, on a gambling night in Leeds, she suffered a massive loss during a game of poker with the guys, and instead of paying up, simply cried until they pardoned her debt. One thing was for sure, whether she won or lost, she really knew how to play the cards in her favor…
19. She Was A Consolation Prize
While working at the Foreign Office in London, Pamela met someone with a rather impressive name and family. He was Randolph Churchill, the son of enigmatic leader Winston Churchill. But Randolph was far from Prince Charming. A cloud of desperation hung around him. He always kept one eye on the ladies and the other on his drink.
On the fateful night they met, he was hoping to have dinner with her landlord, Mary Dunne. But when she proved unavailable, he took her suggestion and asked out her guest—Pamela. The rest, as they say, was history.
20. She Had Standards
Randolph was older than Pamela and attractive—two very important assets in her opinion. And though he barely paid her any attention during their first dinner, his status and political confidence in Britain captivated her interest. By the end of the outing, Randolph proved that he too, saw something in Pamela. He asked her out for another dinner.
This time, he wanted a more private affair—instead of a large party he wanted it to be just the two of them. Alone.
21. She Found Her Golden Ticket
After their second outing, and their first real date, Randolph asked Pamela to marry him—but he was hiding a scandalous secret. What Pamela probably didn’t know was that he’d already proposed to eight other women in the weeks prior to meeting her and that he simply needed to find a wife. Either way, Pamela had more practical notions to consider.
More than anything, she wanted to escape the suffocating confines of Minterne and her family, and this marriage glittered promisingly. On all counts, it seemed to be the answer to all her prayers. And so, she went with her instincts…for better or for worse.
22. She Was Impulsive
Pamela said yes to Randolph. On agreeing to marry him, a whole new world opened up to her. It was one with powerful connections, both social and political. She knew that she didn’t love him, but even more enticing than love were the benefits of his station and the places she could go as the wife of a Churchill. They both got what they wanted.
As such, two complete strangers happily entered into an engagement. But not everybody was happy about the announcement...
23. She Charmed Churchill
Pamela’s friends and family vehemently tried to dissuade her from marrying Randolph. They were undoubtedly aware of his rakish reputation. There was, however, one person in particular with not a single worry about their pending union—Winston Churchill. Upon meeting her future father-in-law at his estate, she enjoyed a very warm welcome.
He eased her anxiety and rebuffed her doubts. He told her: ”Nonsense. All you need to be married is champagne, a box of Cubans, and a double bed". But behind the smiles, Churchill concealed a very personal incentive—one that served his own needs over Pamela’s.
24. She Carried The Torch
When it came to getting his son married off, Winston Churchill had ulterior motives. WWII was brewing, and it was the overarching reason for Churchill’s desire for Pamela and Randolph’s hasty marriage. With Randolph bound for duty and headed to the frontlines, there was the imminent risk of not securing an heir for the Churchill name.
Pamela was a beacon of hope. If she bore a son, she’d eliminate these fears. If she failed and Randolph lost his life in battle, the Churchill line would end. And so, Churchill had everything to gain by cultivating a close relationship with Pamela.
25. She Suffered His Wrath
Pamela entered her marriage blindly, but it wasn’t long before she uncovered the dark side of the Churchill family. Firstly, there was her husband’s excessive drinking and fiery temper. During a fit, Randolph was rash and loud—yelling insults, kicking their furniture, and tramping angrily around the house. Publicly, he embarrassed her at dinners.
The drinking made him aggressively argumentative and he’d often storm away and disappear, leaving her alone and humiliated amongst guests. But this was just the tip of the iceberg.
26. She Couldn’t Keep Up
To make matters worse, Randolph was terrible with paying his bills. He accrued debts through extravagant spending. He put everything on tabs, and when Pamela realized the never-ending trickle of invoices, the worry started to settle in. Her husband was spending far more than he could afford. Consistently living on the edge of financial panic, and facing Randolph's indifference, Pamela had no choice but to turn to her powerful in-laws for help.
27. She Had A Wandering Eye
Luckily for the Churchills, Pamela became pregnant and gave birth to a boy on October 10, 1940—another Winston Churchill. But this happy moment had an unexpected side effect. By producing a male heir, she achieved the end goal. Now there was nothing of her marriage left to salvage, and with Randolph’s incessant financial foolishness, the distance between them became a chasm.
When Pamela set eyes on a very attractive American working for Franklin Roosevelt, her loyalty to her husband wavered. But this was only the beginning.
28. She Cheated
Pamela was 21 when she met the dashing Averell Harriman—Roosevelt’s special envoy visiting Britain. Throughout WWII, her husband’s constant absence gave her leave to pursue other men, and Harriman proved quite the prize. Firstly, and most impressively, he was a millionaire. Secondly, he was 30 years older than her. There was just one problem. He was a married man.
Regardless, for the next two years, the two of them carried on a passionate affair. But just because he was a prime candidate didn’t mean he was the only one...
29. She Wooed Millionaires
Although her affair with Harriman didn’t work out, Pamela kept other lovers to satisfy her needs—all of them with generous wallets. She met another millionaire in John Hay Whitney, and then there was also CBS broadcaster, Edward Murrow. She desperately wished for Murrow to leave his wife and marry her. Though he promised her he would, he never did.
Rejection never seemed to phase Pamela—she simply moved on to the next bachelor in line. And as Pamela quickly learned, keeping rich men in her pocket reaped glorious benefits.
30. They Spoiled Her
During WWII, everyone rationed their goods in order to survive. Pamela, accustomed to having every extravagance at her disposal, wasn’t about to stoop to the average citizen’s standards. Whenever she wanted something she simply had to turn to one of her rich lovers and they’d provide for her. They helped upkeep her lavish lifestyle—their money providing Pamela with nylon stockings, make-up, perfume, and high-end meals.
In return, she kept their beds warm and their hearts happy.
31. She Was An Amazing Lover
Pamela soon garnered a “unique” reputation…for being able to please men. She paid attention to their individual needs and set out to completely satisfy them. Simply put, she fulfilled their every desire—their every fantasy. Many referred to her as “the greatest courtesan of the century". Pamela understood what it was to be a woman in a man’s world, and used seduction to ensnare powerful men.
This earned her a spot next to some of the biggest names of the day.
32. She Met A Prince
Pamela even had an affair with a prince. It was a short-lived fling, but she and Prince Aly Khan—the son of Sultan Aga Khan—made the best of it. During their time together, she allegedly mastered the ability to feign complete interest and absorption while listening to men speak—a red flag perhaps? It became clear that, for both of them, their dalliance was a mere pit-stop on the road to their greatest loves.
For Aly Khan, he went on to meet his future wife, the inimitable Rita Hayworth. For Pamela, it was the fashion icon, Gianni Agnelli.
33. She Admitted Defeat
By December 1945, WWII was over—and it wasn’t the only thing that was ending. It became excruciatingly clear that Pamela’s marriage was done. Her lurid affairs and Randolph’s gambling were the tipping points of an already doomed union. She filed for divorce, claiming that her husband was guilty of deserting her for three years.
When she found release from the shackles of this unhappy business, she dove headfirst into what she described as the happiest period of her entire life. Things were looking up.
34. She Dated A Womanizer
In 1948, Pamela met Gianni Agnelli, a wealthy man with impeccable taste who happened to be the heir to the Fiat empire. But that wasn’t all. He was also a well-known womanizer. Like her prior boyfriends, Agnelli spoiled her. He not only put her up in a posh New York apartment, but also provided her with a car and chauffeur. When her father visited her, Pamela’s well-doing surprised and impressed him.
He couldn’t quite figure out how she afforded her lifestyle on such a small allowance.
35. She Was Only A Mistress
In return for his generosity, Pamela helped keep Agnelli’s busy life organized. According to one of his friends—”She was an ideal housekeeper for Agnelli, she ran his life perfectly". She even converted to Catholicism for him, embracing him in every way she could. But despite her greatest efforts, Pamela couldn’t keep Agnelli from straying.
He had no intention of settling down anytime soon, and even if he changed his mind, he’d never choose a divorcée. Pamela had no idea of the disappointment that lay ahead of her.
36. She Couldn’t Believe Her Eyes
In 1952, four years into their affair, Pamela made a disturbing discovery. She walked in on Agnelli with another woman—Anne-Marie d’Estainville. It was a taste of her own medicine…bitter with a bite of betrayal. She complained and stomped her feet, but none of her admonishments changed his behavior. And then, one night, while driving his new mistress home, Agnelli suffered a violent car crash that severely injured his leg.
As luck would have it, there was one special woman eager to pick up the pieces.
37. She Made A Tough Call
With all her tenderness, Pamela rushed to Agnelli’s side and nursed him through a difficult recovery. But this wasn’t the end of their medical surprises. Later on, Pamela made a shocking discovery—she was pregnant. Whether the child was Agnelli’s or not was unconfirmed. Pamela had a difficult choice to make, but in the end, she chose not to keep the baby and underwent an abortion in Switzerland.
This undoubtedly marked the end of the honeymoon phase, as the relationship began fraying around the edges.
38. She Moved On
When Pamela found out that Agnelli had impregnated another woman—a princess no less—she broke off their long-standing affair. It was painfully clear that Agnelli was never going to marry her, and for her next conquest, she reverted to old habits. Next up was—surprise, surprise—another rich married man. But this time, she gained not only financial support, but also an education.
Baron de Rothschild was from a French banking family and had a lot to offer.
39. She Had A Thing Or Two To Learn
During her short but fruitful fling with Baron De Rothschild, Pamela came away with lessons in art history and wine-making. And even though she entertained the company of two other men during this time, she still gave Rothschild a marriage ultimatum. While waiting for his answer, she kept her options open and agreed to go to the theater with someone new.
He was a Broadway producer responsible for some of the greatest musicals of the century…and she was certainly in for a show.
40. She Seduced A Broadway Producer
Leland Hayward met all of Pamela’s usual standards, and gave her access to another alluring world—theater. With bragging rights including having worked on South Pacific and The Sound of Music, Hayward’s power kept Pamela intrigued. She soaked it all in and learned as much as she could about Broadway. Her interest in his life, keen attention span, and undeniable style helped win the producer over.
When her marriage ultimatum with Rothschild fell through, she gave all her love to Hayward.
41. She Locked Him In
Finally, Pamela’s one wish came true. Although he was still married to socialite Slim Hawks, Hayward popped the question to Pamela, promising to divorce his wife. When the papers went through, she became the fifth Mrs. Hayward. For the next 11 years, she played the doting housewife—always a gracious hostess and ready cook.
Life was untroubled and most definitely luxurious, with the couple moving back-and-forth between their home in New York and their Estate in Westchester County. Life was good, but as they say, all good things must come to an end...
42. She Offended His Kids
When Hayward passed on in 1971, Pamela became a widow. But now, with his fortune on the line, those hoping to inherit his wealth stood at attention. Hayward’s children from his first marriage never really warmed up to their stepmother, and upon his passing, the contents of his will ruffled some feathers. He left half of his holdings to his children, leaving Pamela feeling somewhat cheated.
Her unsatisfied attitude toward her share left a sour taste in the mouths of the Hayward children. From then on, they never had a good word to say about her.
43. She Rekindled An Old Flame
After Hayward passed, Pamela didn’t waste a single second. Only a day after the funeral, and with her tears barely dry, she arranged to meet with “the one that got away”—79-year-old Averell Harriman. He too was a recent widower, and now that they were both free to date again—not that marriage ever held them back in the past—they reconnected and rekindled their long-dormant romance.
But what was the takeaway for Pamela? How would this relationship benefit her? After all, when it came to Pamela, there was always a profit to be made.
44. She Was Opportunistic
By going after Harriman, Pamela earned a disturbing new nickname. People called her “The Widow of Opportunity". Only six months after she lost her husband, Pamela and Harriman tied the knot. With his fortune including a railroad company, an estate in Virginia, and a private jet, Pamela Harriman had a lot to gain. But even more enticing than his assets were his connections.
Harriman’s involvement in the Democratic party dangled in front of her as a VIP pass into his political circles.
45. She Proved Herself
With her new American citizenship in one hand and her husband’s influence in the other, Pamela Harriman dove headfirst into the world of politics. She helped create a fundraising system for the Democrats—a political action committee nicknamed “PamPAC". In 1980, the National Women’s Democratic Club dubbed her “Woman of the Year". This initial foothold, and its resulting recognition, was only the beginning of Pamela’s illustrious political career.
46. She Sold A Picasso
When her husband passed on in 1986, Pamela Harriman took control of his $115 million fortune—but of course, there was a caveat. As with her previous marriage, she ran into a sticky situation with his surviving relatives regarding the inheritance. They accused her of making terrible investments and squandering the fortune.
As a result, a civil suit forced her to sell some of her priceless pieces including a Matisse, a Picasso, and a Renoir. But these speedbumps weren’t enough to throw her off track. Pamela had her eyes on the prize.
47. She Took It Seriously
In 1993, Pamela Harriman received a high honor when President Bill Clinton appointed her United States Ambassador to France. All those years spent schmoozing and perfecting her social skills truly paid off, because now she could apply them to matters of utmost importance—questions of N.A.T.O expansion and International Trade.
Over a lifetime, Pamela had transformed from a naive country girl into an experienced woman in politics.
48. She Was Honored
Pamela Harriman spent four years serving as an ambassador until her passing in 1997. While enjoying a swim at the Paris Ritz, she suffered a fatal cerebral hemorrhage. Both the President of France and The US President recognized her contributions. At her funeral, Bill Clinton spoke highly of her public service. But throughout her rather scandalous lifetime, not everybody had kind words for Pamela.
49. She Neglected Her Son
Winston Churchill, Pamela’s only son, claimed that his mother ruined his childhood Christmases because, as he put it, she was “too busy [sleeping] around". Her first husband, Randolph Churchill, used the same language to describe his wife, and like his own son, used the W-word. But for Pamela, the pros of her chosen lifestyle greatly outweighed the cons.
For a woman of her time, dating and marriage were economic considerations. And so, she always did what she wanted—what she thought was necessary,
50. She Turned Things Around
In 1957, Pamela Harriman desperately sought an invitation to the Embassy reception in Paris, as it was Queen Elizabeth’s first trip to France. But to her dismay, her poor reputation dashed her chances. Cynthia Jebb—the wife of the British ambassador—scoffed at the very idea of Pamela showing her face at the event. She said: “I will not have that tart in the Embassy". Well, it took years, but Pamela finally showed her.
Luckily for Pamela, in the decades that followed, her strategic climb to the position of US ambassador proved that a discreditable reputation didn’t end one’s bid for power and respect. Also, she was the first woman to hold the position. You go, Pamela!