Porfirio Rubirosa epitomized the playboy lifestyle of the 1950s by living in luxury at the expense of others. Subsisting on pleasure, polo, and fast cars, Rubirosa played a dangerous game and spent his entire life trying to maintain a dodgy equilibrium. By employing his devil-may-care charm, he refused to settle for less—never taking “no” for an answer.
1. He Had Strong Roots
Born in the Dominican Republic in 1909, Porfirio Rubirosa Ariza was the youngest of three children. When he was only six years old, his father—Pedro Rubirosa moved to Paris and served as a diplomat. And so, Porfirio and his family left the Dominican Republic and made Paris their new home. Pedro Rubirosa, with his illustrious career and reputation, influenced his son in more ways than one.
2. His Father Was A Womanizer
When it came to his father, Rubirosa had a lot to admire—his powerful presence, successful public life, and impeccable taste. He also witnessed, first-hand, the power of seduction. As an impressionable youth, Porfirio noted his father’s penchant for womanizing and saw something to aspire to. But while Rubirosa’s father loved women, he was also an inexhaustible worker. Rubirosa, on the other hand, was a pleasure-seeker all the way, and had a knack for masking his distaste for work with his magnetic personality…
3. He Was Charming
When he was 17, Rubirosa returned to the Dominican Republic. Following in his father’s footsteps, he joined the army where he rose through the ranks. By the time he was 20, he boasted the accolade of Captain, not only in the army, but also in his nation’s polo team. In fact, it was at a polo match that Rubirosa came face-to-face with a very intimidating character—the brutal dictator Rafael Trujillo.
With his charm at the ready, Rubirosa impressed the hardened leader, winning him over, and winning himself a personal invitation to Trujillo’s quarters…
4. He Didn’t See Her Coming
The next morning, Rubirosa reaped the rewards of a good first impression when Trujillo made him a generous offer too good to refuse—the position of Lieutenant of his Presidential Guard. Luckily for Rubirosa, this new job wasn’t all work and no play. For one of his very first assignments, he had the important task of receiving the dictator’s 17-year-old daughter at the airport.
It was a simple enough mission, until Rubirosa caught sight of her. She was absolutely stunning, and stunning girls were one of his greatest weaknesses…
5. He Spoke The Language Of Love
Trujillo’s daughter Flor de Oro, fresh from her studies in France, walked off the plane and straight into Rubirosa’s clutches. Striking up a conversation in French and demonstrating his alluring presence, Rubirosa secured himself an invitation to a ball at the Presidential palace. But his interest in the boss’s daughter didn’t end there.
At the ball, Rubirosa capitalized on his enchanting first meeting with Flor de Oro by defying etiquette and dancing with her for every number. Treading on thin ice, his objectionable behavior didn’t go unnoticed for long.
6. He Fell For The Boss’s Daughter
Rubirosa’s interest in Flor de Oro sparked his employer’s fury, and he paid a considerable price. This dalliance threatened his prospects and consequently, Rubirosa found himself decommissioned. But that wasn’t all. To escape Trujillo’s wrath, he went into hiding at his family’s coffee plantation where he moldered in boredom.
After 8 days, Rubirosa finally received word from his love—he was to meet her in secret at a photobooth, safe from the prying eyes of those seeking to tear them apart…
7. He Scared Her
The secret meeting proved fruitful. Flor de Oro proposed to Rubirosa, and the couple married in 1932. But their wedding night was far from the fantasy Flor had in mind. Completely naive in the act of intimacy, she was petrified when faced with losing her virginity. As she confessed, ”I was scared—this thing lurching at me! I was disgusted…and became afraid, running all over the house.”
Unsurprisingly, their marriage followed suit, quickly fading into a sad echo of their initial infatuation and falling prey to Rubirosa’s own shortcomings.
8. He Couldn’t Resist
When Rubirosa married Trujillo’s daughter, he won himself back into his father-in-law’s good graces and salvaged his career. But while Rubirosa ventured to Berlin, and eventually Paris, as a diplomat, his true interests lay far beyond his work. Beautiful women abounded and he couldn’t resist the temptations of the city. In Paris, he went out on night-long benders only to return home rumpled and covered in lipstick.
When his wife questioned where he was, he took to beating her. After 6 years, this infidelity and ill-treatment led to a divorce. Then again, Rubirosa also led a questionable professional life.
9. He Made A Difference
After slighting the daughter of a powerful man, Rubirosa was unable to return to his home for fear of Trujillo’s vengeance. Without his wife’s financial support, he turned to selling Dominican visas to Jews looking to escape Europe. Seemingly self-motivated, this venture resulted in some philanthropic fallout that changed the lives of many.
But Rubirosa wasn’t always so generous in his money-making schemes—sometimes he was downright shady…
10. He Was A Thief
Rubirosa agreed to use his diplomatic passport to retrieve a jeweler’s store inventory that was hastily left in Spain at the outbreak of the civil war. But when Rubirosa returned from Madrid, there was a distinct problem—$180,000 was missing from the inventory. Where had it disappeared to? According to Rubirosa, his mission had hit a terrible snag—he’d been ambushed and shot at—and the money was taken from him against his will.
But his story had gaping holes throughout and there wasn’t a single bullet hole in his car. The suspicious evidence begged an obvious question—Was Rubirosa a thief?
11. He Turned A Blind Eye
In order to mend fences with Trujillo, Rubirosa agreed to be his tour guide in Paris. At the Eiffel Tower, Trujillo lecherously eyed a pretty girl selling postcards. Eager to make his ex-father-in-law happy, Rubirosa made introductions, ushering the two of them into an elevator where they could be alone. Upon return, the girl emerged dishevelled and distressed while Trujillo boasted a wide grin of satisfaction.
Grateful to Rubirosa for his discretion, he welcomed him back into his favor and even granted him a new title—Commercial Attaché to France. But where he found peace with one danger, another loomed on the horizon.
12. He Had Love On His Side
In 1942, Rubirosa came up against the challenges of WWII. With his opinions flying in the face of the German regime, the Vichy government interned Rubirosa for five months in a German hotel. Luckily for him, he had a beautiful woman on his side. Celebrity French actress, Danielle Darrieux—with whom he was deeply in love—obtained his release in exchange for doing a promotional stay in Berlin.
With the taste of freedom fresh on their lips, the couple hoped to marry. But the road to forever proved harsher and more dangerous than they could have ever anticipated.
13. He Was A Hero
Rubirosa married Darrieux soon after his release, but never enjoyed the peace of newlywed bliss. Darrieux harbored sympathies to the German regime, and this attracted aggression. In 1944, the pair was ambushed in Paris on their way home from a nightclub. Driving unprotected in an open car, they were completely vulnerable to their attackers.
In a stunning act of heroism, Rubirosa shielded his wife’s body with his own when the shots rang out, incurring three bullets near the kidneys. One thing was for sure—they had to escape the dangers of the city.
14. He Went Into Hiding
With no other choice, the couple hid from German authorities, eventually spending the last months of the occupation on Darrieux’s French farm. This gave Rubirosa the chance to pick up some farming skills—milking his own cow and tending pigs and sheep. But their safety was never a sure thing. On one occasion, they narrowly escaped capture on the farm, hiding in a friend’s barn for a few days until the Germans retreated.
Together, Rubirosa and Darrieux went through the ringer. But was their shared trauma enough to sustain their bond?
15. He Was A Hot Commodity
Darrieux introduced Rubirosa to the world of cinema, and with that, many other eligible women. Journalist Doris Duke, an heiress worth $100 million, interviewed Darrieux at a hotel in Rome with Rubirosa present. During this first meeting, a spark of attraction flared between Rubirosa and Duke. As Duke became determined to have Rubirosa for herself, she used her money to tilt the balance.
Allegedly, Duke offered Darrieux $1,000,000 to divorce Rubirosa. This entire fiasco led to the collapse of a perfectly good marriage. And just like that, Rubirosa was on to the next.
16. He Married For Money
In 1947, only a year after their first meeting, the couple made a rash decision. Rubirosa and Duke set a date for their big day. She towered over him in a green Dior suit and he, anticipating his fortune, lounged happily in a grey pin-striped number. Just before the wedding ceremony began, Duke’s lawyers arrived with a prenuptial agreement for Rubi to sign.
He drank copiously before signing, and by the end of night, had fainted into a contented delirium. His life of luxury awaited.
17. He Loved His Toys
There are definitely advantages to marrying one of the richest women in the world. For instance, the gifts! Gone were the days of ordinary, cliché presents. Instead, Rubirosa received sports cars, polo ponies, and—wait for it…even a B-25 bomber. Swimming in opulence, there seemed nowhere to go but up. Unfortunately, it wasn’t long before Rubirosa’s high-flying lifestyle took an inevitable nosedive…
18. He Didn’t Play By The Rules
Duke expected her husband to always be available to her, while Rubirosa wanted to do as he pleased. Sooner than later, Duke caught him red-handed with his former wife, Flor de Oro. Due to the unexpected prenuptial he signed the day of his wedding, Rubirosa only gained a 17th-century house in Paris and a meager $25,000 a year alimony until he remarried.
His fondness for rule-breaking simply didn’t coincide with the pressures of monogamy. He’d have to find another way to make a pretty penny.
19. He Went Treasure Hunting
Once again, Rubirosa needed a new way to make money. When a stranger approached him with the fantastical notion of sunken treasure off the coast of the Dominican Republic, he was all in. In the end, it was a doomed mission. The pirate adventure rapidly turned into a series of unfortunate events. With a drunken crew that he had bailed out of prison, he fought turbulent storms that only led to the sinking of his ship.
He found no money, and lost much of his capital. But despite this failure, Rubirosa still proved himself nothing if not resourceful.
20. He Was A Man Of Pleasure
Rubirosa considered his profession to be ‘a playboy’. Indeed, he valued leisure as one of his top priorities. When questioned on the notion of work he exclaimed: “Work? It’s impossible for me to work. I just don’t have the time!” Perhaps even more than his pursuit of leisure was his pursuit of women. He made women his business of choice, wooing such high-profile celebrities as Ava Gardner, Rita Hayworth, and Veronica Lake. He always had something to gain.
21. He Loved His Job
Rubirosa was very attentive to women and it paid off. He learned that although he didn’t have to work hard to attract them, handling them was another story—time-consuming in every way. When asked by his friend Frank Sinatra if he ever had a real job, he said—”Women are my full-time job.” He certainly knew every trick in the book.
22. He Knew What Women Wanted
Rubirosa knew that women desired undivided attention above all else, and ensured that when engaged in a conversation with a woman of any age, his head wouldn’t swivel. He always maintained piercing eye contact and actively listened to their wants and needs. Over drinks, this mindfulness was his superpower, but beneath the sheets, he had a secret weapon at his disposal…
23. He Was Well Endowed
In Parisian restaurants in the 1950s, the sixteen-inch pepper mill was commonly referred to as “the Rubirosa.” Rubirosa’s friend, fashion designer Oleg Cassini explained that the name referred to Rubi’s “most remarkable piece of equipment”—reportedly, eleven inches long with substantial girth. This undoubtedly enhanced his playboy reputation and aroused the curiosity of his female contemporaries. This was the start of something sensational.
24. He Had A Nickname
Whispers about Rubirosa’s large endowment began circulating, and gossip spurred intrigue and conversation—women wanted more. A Vanity Fair article noted—“Rubi’s constant state of erection earned him the nickname Toujours Pret, which in English is the motto of the US Coast Guard: ‘Always ready.’” But behind this playful nickname lay a darker reality.
25. He Couldn’t Finish
Rubirosa suffered from the medical condition priapism. His friend, Cassini offered insight into his affliction—“He was in almost constant state of arousal but unable to be satisfied. He achieved orgasm very rarely, and then only after hours of struggle.” This was no small matter as priapism offered a range of sensations ranging from annoying to excruciating. And this wasn’t the only pitfall…
26. He Couldn’t Have It All
Despite being married five times and having numerous trysts and ladies’ room ‘quickies’, Rubirosa never sired any children—he was completely sterile. However, the root cause of his sterility remains unknown as well as his thoughts on the matter. As such, without the fear of pregnancy, women were more willing to engage in coitus with him. Whatever his struggles with procreation may have been, Rubirosa never let his reputation impede him from capitalizing on his powerful erections.
27. He Tried Again
Playing upon his “Toujours Pret” status, Rubirosa wanted to endorse a product from the Dominican called Pego Palo that purportedly worked like an aphrodisiac. It was made of tree bark and herbs and described as “liquid Viagra.” However, his lack of funds impeded him from seeing the project to fruition. Similarly, five years later, he tried to go into business with fellow playboy Gunter Sachs by creating a perfume called “Rubi.”
They planned to sell the scent in ruby-colored vessels, cleverly riffing off its name, but once again, this ambitious idea fizzled out. But Rubirosa had nothing to fear—there were countless ways for his legacy to survive.
28. He Was Immortalized
With his rugged good looks and standing at 5 ft 9”, Rubirosa had an absolutely scandalous bedroom reputation. According to lore, he bedded “thousands of women” in the 50s and 60s. His conquests were made into a satire by Italian singer Fred Buscaglione in the song Porfirio Villarosa. A classic of the 50s, the lyrics called out to Rubirosa by name—“Porfirio Rubirosa is the idol you never knew you had.
He was fast, he was dashing and he left 1,000 women screaming his name.” Although coined as a lady’s man, Rubirosa’s appeal extended beyond his romantic conquests…
29. He Was The Life Of The Party
Rubirosa was attentive and chivalrous, excelling in shows of generosity and courteousness. Many witnessed him performing polite gestures such as opening doors or lighting a woman’s cigarette. As a diverting conversationalist, Rubirosa knew how to cut through a crowded room—keeping the party alive at all times. His friend, Cassini, described Rubirosa as a Don Juan who was both a man’s man and a ladies’ man. Everywhere he went, he charmed all walks of life…
30. He Was High Profile
Connected romantically to many Hollywood actresses, singers, and political figures, Rubirosa had an extensive list of conquests under his belt. Gossip magazines had plenty to write about—his high-profile marriages, affairs, and everything in between. He even associated with the Kennedys until indiscrete mafia associations surfaced—although nobody knows for sure how far those associations went. He was in high demand, not only in the bedroom, but also in the locker room…
31. He Was A Man’s Man
Rubirosa was the very definition of machismo. Fellow polo-player Gerard Bonnet described how men looked up to Rubirosa—“Everyone wanted his style of macho. He believed in the bond of male friendship. All the men I know loved Rubi. The ones who didn’t were jealous of him.” No doubt a key player in antiquated boys’ clubs, Rubirosa was always Mr. Popular. While he placed first among his peers, coming first in ruthless competition was another story entirely.
32. He Wasn’t Number One
Rubirosa made friends with race car drivers and, with his affinity for the sport, decided to try the profession on for size. In 1950, he entered his very first race in the prestigious 24 Hours of Le Mans, but his car never finished. Upon entering for a second time, he experienced a similar failure. To top it all off, during the only Formula One race he ever entered, he called in sick and never drove at all. But despite never enjoying a lauded driving career, he still relished in the thrill of the ride.
33. He Loved A Challenge
All women were romantic considerations for Rubirosa, even the wives and girlfriends of his polo and race-car driving peers. Accomplished men filed for divorce on the grounds of adultery, with Rubirosa named as a co-respondent. One of the married women was none other than Zsa Zsa Gabor—an actress and socialite. In 1953, Rubirosa crossed paths with her at New York’s Plaza Hotel. After some innocent small talk, she returned to her suite for a nap. But when she awoke, she couldn’t believe her eyes.
34. He Spoiled Her
Zsa Zsa Gabor awoke to a room completely covered in flowers. The note that accompanied them came directly from Rubirosa himself and read “To the most beautiful of women.” Easily swayed by first impressions, he pursued her with enthusiastic fervor, inundating her with flowers and phone calls, spoiling her as much as he could. But this ardor was a mere preview of his darker, more possessive side. He was too used to getting what he wanted…
35. He Was Possessive
When Gabor’s husband finally filed for divorce, Rubirosa proposed a marriage ultimatum. But despite Gabor’s lust for Rubirosa, she still felt conflicted by her love for her husband—something Rubirosa wasn’t ready to hear. Never willing to play second fiddle, he lashed out in anger and hit her. In his mind, he already owned her. In a twisted response to his insult, Gabor defended him by saying, “The fact that he hit me proves that he loves me. A woman who has never been hit by a man has never been loved.”
36. He Married His Ex-Wife’s Rival
In 1953, while still interested in Gabor, Rubirosa faced a dwindling bank account. That’s when one of the wealthiest women in the world entered the picture: American heiress Barbara Hutton. Although by no means a youthful beauty, 40-year-old Hutton had all the financial makings of a queen. Hutton also harbored a long-standing rivalry with Rubirosa’s ex-wife Doris Duke, and if she married Rubirosa, it would be the finest form of retribution.
She was his ticket to luxury, and he was the perfect revenge. With mutual benefits, this unlikely pair agreed to marry.
37. He Couldn’t Stick It Out
Unfortunately, during this time, Hutton wasn’t at her strongest and teetered on the edge of a mental collapse. Alongside Rubirosa’s lack of empathy, Hutton’s poor health only made for a shaky foundation. Even ex-girlfriend Gabor didn’t have high hopes for the marriage and sat back to watch it unfold. “I give them six months,” she sneered. “In a couple of weeks, this man will be after me again.” Jetting off on their honeymoon, Rubirosa and Hutton embarked on their shaky union.
38. He Was Insatiable
Hutton did everything she could to keep Rubirosa happy. She showered him with exorbitant gifts—an enormous coffee plantation, 40 suits, 8 polo ponies, an airplane, and last but not least—$2.5 million in cash. She spent upward of $66,000 on him every single day, but none of it made any difference. Rubirosa was still miserable. He wasn’t a homebody in any sense of the word, and no amount of money could alleviate his boredom.
As the days passed, it became clearer and clearer that the marriage was a disappointment for both parties.
39. He Was A Bachelor
After only two weeks, Hutton left her new husband’s side and moved in with her aunt. Following this desertion, their marriage completely imploded—it only took 53 days. Rubirosa was never cut out to be the husband Hutton needed, and he missed his free-wheeling, bachelor lifestyle and couldn’t wait to be rid of his sickly wife. ”She stays in bed and reads all day. It’s a very boring life,” he complained. Luckily for him, he didn’t leave empty-handed. Financially, this marriage earned him an overwhelming profit.
40. He Gave It His All
Fresh from a failed marriage and riding in his new jet, Rubirosa indeed headed back to the arms of Zsa Zsa Gabor. After reuniting with Gabor, he felt inspired—he wanted to give acting a shot. In preparation for a movie called Western Affair, he traded in his late-night escapades for acting lessons. Unfortunately, the film never made it to the screen…
Just as it received the greenlight for production, the Immigration and Naturalization Service swooped in and barred Rubirosa from starring in it. With his dreams dashed and pride hurt, he turned his back on the silver screen.
41. He Won Her Over
After returning to Paris in 1956, 47-year-old Rubirosa fell in love with an aspiring teenage actress and model Odile Rodin. “I fell in love with her the first moment I saw her. She was young, fresh, so beautiful, and again, a certain mysteriousness,” he said. But dating Rodin wasn’t as easy as Rubirosa expected. Rodin’s mother, sensing danger afoot, forbade her daughter from entertaining his advances.
She quickly changed her tune, however, after watching Rodin and Rubirosa’s chemistry flourish during a single slow dance. After that, they couldn’t keep their hands off one another.
41. He Met His Match
Rubirosa fell madly in love with Rodin and her joie de vivre. She too enjoyed the all-night party scene and the exciting company it afforded. Rodin effectively turned the tables on Rubirosa by exerting a unique magnetism over him that no woman ever could—“All my life I’ve controlled women. Every woman I’ve ever met, except this one. She is under my skin.”
The couple wed in October 1956, five months after meeting. But despite his seeming surrender, Rubirosa still sought ways to control his new wife.
42. He Called The Shots
Rubirosa delighted in mentoring his new bride—Pygmalion style. He preferred she look more like Grace Kelly than Zsa Zsa Gabor. From the amount of hairspray in her hair to her conservative dresses, Rubi made his preferences known. According to a friend, Rodin resisted his control by refusing to wear any underwear. But his specificity for hygiene extended beyond his need for spousal control.
43. He Appreciated The Finer Things
Always immaculately groomed, Rubirosa had impeccable style—he chose his attire carefully, right down to his monogrammed boxer shorts. This reverence also extended to his skin and physical shape. He protected his skin by treating it with honey and limiting sun exposure, and exercised regularly to maintain his lean build. After acquiring his 17th-century house in his divorce settlement with Duke, he then converted the entire top floor of the home into a boxing ring and bar. During that time, sparring became an essential part of his physical upkeep.
44. He Spoke Their Language
Rubirosa was a man of many talents, linguistics being one of them. Able to speak five languages, Rubirosa worked at Dominican embassies in France, Germany, Argentina, Italy, Cuba, and Belgium. His abilities provided him access to a wide number of political circles. I936, he shared the Fuhrer’s box at the Berlin Olympics. And when he became Ambassador to Cuba, he witnessed the Cuban Revolution first hand, even striking up conversations with Fidel Castro. Rubirosa even had the opportunity to speak with the US President…
45. He Lost His Benefactor
In 1961, “a 31-year reign of terror”—known as the Trujillo era—ended with the assassination of the dictator himself. After his passing, Rubirosa continued to work for Trujillo’s son and successor, Ramfis, who proved just as unstable as his father. When Ramfis attempted to have the Venezuelan president taken out, the US responded by placing an embargo on the Dominican Republic. Rubirosa could only hope that his charm was capable of persuading the US president…
46. He Got Fired
Sailing on a yacht with John F. Kennedy, Rubirosa attempted to secure US support for Ramfis’ new regime. But Rubirosa and Ramfis weren’t on the same page…While Rubirosa put in the work, Ramfis chose to take the money and run, pilfering $200,000 from the treasury and fleeing the country. Subsequently, the new Dominican president fired Rubirosa, essentially destroying his cushy safety net and plunging him into financial uncertainty. His future stretched before him—bleak and unforeseeable.
47. He Was Rumored To Be A Political Assassin
The loss of Rubirosa’s job meant the loss of diplomatic immunity. Without this protection in place, the New York District Attorney could investigate his presumed involvement in the previous disappearances and suspected murders of Trujillo’s opponents. Although he never faced charges, his career never recovered—his powerful reign was officially at an end. Rubirosa found himself caught in a downward spiral.
48. He Couldn’t Cope
Never cut out for an ordinary life, Rubirosa fell into a deep depression. His friends had moved on with their lives and were now working, and his financial concerns weighed heavily on him. Mildred Ricart, the wife of one of his friends, commented, “For Rubi to live without money was torture.” His previous life of fun and games taunted him, then threw his sad reality into relief. Unbeknownst to him, he wouldn’t have to live like this for long…
49. He Had A Tragic Ending
In 1965, Rubirosa enjoyed a brief moment of glory when his team won the Coup de France Polo tournament. But this euphoria plummeted immediately. Shortly after an evening of intense celebration, Rubirosa—only 56 years old—drove his Ferrari into a tree. He didn’t survive the impact. His friend, Cassini questioned whether the crash was a result of drink or depression. Either way, it was a sad and ironic ending for a man who spent much of his life in the fast lane.
50. He Inspired A Novel
It isn’t a surprise that New York Times best-selling author Harold Robbins picked up a pen to write a novel loosely based on Rubirosa’s life. After its publication in 1966, The Adventurers also became a film adaptation. The life of Porfirio Rubirosa certainly provided Robbins with the juiciest material to pull from. He was, in so many ways, a character larger-than-life—an irresistible rogue, an opportunistic gigolo, a savvy diplomat, and perhaps above all—“a big kid.”