By the time of his death in 2006, Oleg Cassini had earned his reputation as a legendary Lothario who seduced some of the twentieth century's most celebrated women. He was engaged to Grace Kelly, married to Gene Tierney, had affairs with Marilyn Monroe, Betty Grable, Lana Turner and became famous as Jacqueline Kennedy's personal couturier during the halcyon days of Camelot.
In the 13-years since Cassini's passing; a battle over his $60million estate, waged between his widow, Marianne Nestor and his four grandchildren has dominated his legacy with sensational headlines. It is only now, after years of protracted litigation that a settlement is near with news of a court-ordered, public sale of Cassini's estate. A cache of personal letters from Jacqueline Kennedy and Grace Kelly, mementos, photographs and fashion drawings are among the items auctioned off by Doyle – revealing the private life of an illustrious playboy and a bygone era.
Oleg Cassini was the son of an impoverished Russian count loyal to the Tsar and Italian countess who lost everything during the 1917 Bolshevik Revolution. The family was forced to rebuild their lives in Florence where Cassini's mother opened a small clothing boutique. Upon completing his education in fine art, Oleg set sail for America in 1936 with only 'a tuxedo, two tennis rackets, a title and talent,' he wrote in his autobiography.
Oleg Cassini and Hollywood actress, Gene Tierney dine at the Stork Club in New York (left) and the legendary West-Hollywood nightclub Mocambo. The couple met while Cassini was working in Hollywood as a costume designer, they were married for 12 years and had two daughters named Daria and Christina
Their toxic marriage was marked by affairs and the tragedy of their daughter - Daria, who was born with severe mental and physical disabilities. Tierney had affairs with Tyrone Power, J.F.K and Howard Hughes; the latter of which paid for Daria's medical expenses till the day she died
Oleg Cassini sits with actress Natalie Wood on a zebra lounge chair at the exclusive New York club, El Morocco. Diane von Furstenberg told the New York Times, 'He was a true playboy, in the Hollywood sense'
Eventually, Cassini was joined by his parents and younger brother, Igor Cassini- who himself would go on to become a powerful gossip columnist under the pen name Cholly Knickerbocker. He could make or break reputations and made national news in 1939 when he was kidnapped, tarred and feathered by members of Virginia high-society in retaliation for a less than flattering story.
The Cassini brothers defined 'the jet set,' in fact it was Igor (also known as Ghighi) who originally coined the phrase. They were international playboys, elegantly dressed, and distinctly old-world in their endeavors: polo-ponies, yachting, skiing in Charmonix and exclusive dinner clubs. The common thread running through Oleg Cassini's entire life up until his death at 92-years-old was the women he entertained: movie stars, models, debutantes, heiresses and ingenues.
'They were like pirates with a gloss of education and culture,' said gossip columnist Liz Smith who worked as Ghighi's assistant for a short time. 'They slept with everybody. Ghighi would walk into the office and say, ‘Last night I went to dinner at Mrs. [Babe] Paley’s. I had slept with every woman at the table.''
A note from Jacqueline Kennedy to Cassini in 1961 sums it up best: 'Casanova reminds me of you.' In a 2001 interview with Newsday, Cassini said: 'Am I a Casanova? Sure, Casanova was a cultured man who conquered women. Women love me. I give them total devotion. We talk. We laugh.' He continued, 'I've had the greatest women in the world. Women loved me, but men were my enemies.'
One of these women was his first wife, Merry 'Madcap' Fahrney, a cough-drop heiress who Cassini claimed that she only married him for his aristocratic title. Count Cassini was her fourth husband in a line of eight marriages and they divorced after only two years.
Grace Kelly wears a dress designed by her fiance, Oleg Cassini to the premiere of the 1955 film, Rear Window. Kelly broke their engagement to marry Prince Rainier of Monaco, but years later she admitted to a journalist: 'Do you realize if my mother hadn't been so difficult about Oleg Cassini, I probably would have married him?'
This photo taken of First Lady Jacqueline Kennedy and her sister, Lee Rasziwill while in Pakistan was one of the items up for auction. Cassini designed their wardrobe for the state visit and both sisters expressed their gratitude with messages on the front reading: 'For Oleg - Who made us the two best dressed women in Asia -Jackie' and 'For Oleg - Au revoir Givenchy, Bonjour Cassini! - Lee'
Also on the block was this letter written by Jackie before her husband John F. Kennedy was elected president. In it, she explains how difficult it will be for her to find and purchase clothes as a First Lady. She writes: 'Givenchy is where I have always gone - It would be SO easy if I could get everything from him but I can't and if Jack were elected I'd never expose myself to that charge'
This letter from Jacqueline Kennedy written on stationary from The White House was also part of the estate. In it, she thanks Cassini for a set of ties that he gave to her husband, 'Jack;' Kennedy also congratulates Cassini on the success of his recent collection, writing: 'Diana Vreeland called to say how good she heard it was ... Congratulations I am so proud of you.' The letter finishes by her lamenting the lack of space at their rented Virginia country estate, where she writes: 'I can't even shelter a pony for Caroline'
Cassini left New York for Hollywood in 1940 where he began a modest career in the wardrobe department for B-rated movies. Growing up, his mother always told him that - 'With a tennis racket and a dinner jacket, you'll be able to go anywhere in life.' Indeed, it was on the tennis court where Cassini got his first career break after competing and winning a doubles match at the West Side Tennis Club. His partner happened to be the head of Paramount Pictures and coincidentally was looking to hire a new full-time designer, a job that saw him create seminal looks for all of Hollywood's silver screen sirens: Veronica Lake, Rita Hayworth, Audrey Hepburn, Marilyn Monroe, Anita Ekberg and the glamorous 20th Century Fox talent - Gene Tierney. Cassini cut through Sunset Strip parties and nightclubs with his friends, John Barrymore and Errol Flynn but eventually captivated Tierney with his effortless charm.
Later in life, Cassini reminisced about old Hollywood to Newsday: 'Now, all the girls want to show what great actresses they are, wearing jeans and no makeup. The men then were beautiful looking, too -- Errol Flynn, Tyrone Power. Today there's Dustin Hoffman and Al Pacino.'
The start of Cassini and Tierney's 12-year-long tempestuous relationship began in 1941 after they eloped to Las Vegas because her parents did not approve of the union. It wasn't long before both parties were having affairs with various people. One of Gene's was Howard Hughes; Cassini writes in his biography of how he was reduced to fisticuffs with the aviation tycoon at a party hosted by Jack Benny. Cassini's philandering pushed Tierney into the arms of other leading men of the era: Tyrone Power, Spencer Tracy, Desi Arnaz and Kirk Douglas.
The start of Cassini and Tierney's 12-year-long tempestuous relationship began in 1941 after they eloped to Las Vegas because her parents did not approve of the union. It wasn't long before both parties were having affairs with various people. One of Gene's was Howard Hughes; Cassini writes in his biography of how he was reduced to fisticuffs with the aviation tycoon at a party hosted by Jack Benny. Cassini's philandering pushed Tierney into the arms of other leading men of the era: Tyrone Power, Spencer Tracy, Desi Arnaz and Kirk Douglas.
Cassini enjoyed retelling the anecdote of the time he enlisted political patriarch, Joe Kennedy, to help him persuade Grace Kelly into marriage. Instead of playing the part of wing man, Kennedy made a move on Kelly himself, telling her: 'I know this donkey. He's a pretty good boy, but you'd be making a terrible mistake to marry him'
Grace Kelly was absolutely besotted with Cassini even though her parents didn't approve of their relationship. In one of the four letters up for auction, she playfully wrote to Cassini: 'I think I'd rather have a ring instead of an automobile.' In another letter she chastises Cassini for being jealous of her co-star Bing Crosby: 'You have upset me so that I could die...It is incredible to me that having dinner with Lizanne and the Crosbys can make you behave like a school boy'
After the divorce with Gene Tierney was final, Cassini moved back to New York where launched his own label on the reputation he built as a designer in Hollywood
In 1943, Tierney was pregnant with their first child, Daria, when she contracted measles in her first trimester from an eager fan while on tour with the USO in Germany. As a result, Daria was born blind with severe mental disabilities and had to be confined to an institution for the rest of her life. To the credit of Howard Hughes, he covered Daria's medical expenses until the day she died. Tierney never forgot the favor.
Gene Tierney posed for a photo in 1951 while boarding an airplane with her daughter, Christina. Tierney never recovered from tragedy of Daria's health issues. She spent the rest of her life in and out of mental hospitals for bi-polar disorder, undergoing 27 rounds of electro-shock treatment
'Emotionally, it's a horror…in my many disorderly thoughts, I considered killing her- and killing myself,' said Cassini to Newsday about the tragedy of his daughter's life. The event also affected Tierney, who spent bouts of time throughout the rest of her life in mental hospitals for bi-polar disorder, undergoing 27 rounds of electro-shock treatment. The healthy birth of their second child, Christina in 1948 did little to fix the relationship.
It wasn't long after, when Tierney fell madly in love with a young John F. Kennedy who was just back from serving the war. They carried out a short-lived affair together in Palm Springs before he made it clear that his religious and political aspirations meant that he couldn't marry a divorced woman. By 1953, Cassini's marriage to Tierney was officially over; Gene moved on to the Prince Aly Khan, whose own marriage to Rita Hayworth was deteriorating, while Oleg set his sights on Grace Kelly.
It wasn't long after, when Tierney fell madly in love with a young John F. Kennedy who was just back from serving the war. They carried out a short-lived affair together in Palm Springs before he made it clear that his religious and political aspirations meant that he couldn't marry a divorced woman. By 1953, Cassini's marriage to Tierney was officially over; Gene moved on to the Prince Aly Khan, whose own marriage to Rita Hayworth was deteriorating, while Oleg set his sights on Grace Kelly.
By the mid-fifties, Cassini moved back to New York where launched his own label on the reputation he built in Hollywood. Living with her father in his two-bedroom apartment on Fifth Avenue, Christina explained to Maureen Orth of Vanity Fair that it was too easy 'for me to witness the traffic of my dad's many girlfriends.' She recalls the early days of Cassini's relationship with Grace Kelly and how one time she caught them getting ready for an evening when he noticed Kelly didn't have a bow in her ponytail. 'You can't go out like that' said Cassini before he fastened one of his bow ties in her hair. Cassini designed a lot of Kelly's iconic looks, most notably, the mint green, satin gown she wore to accept an Oscar for her 1955 performance in The Country Girl.
Cassini designed over 300 silhouettes for Jacqueline Kennedy during her tenure in The White House like this orange silk dress she wore for a state visit to India. He also coordinated every aspect of her wardrobe, from shoes and hats to gloves and handbags - the First Lady called him her 'Secretary of Style'
Cassini invented 'Jackie's look' comprised of meticulously tailored suits,
