JFK and Howard Hughes

Part OneDeath of The Original Playboy: Gunter Sachs, Porfirio Rubirosa
Part TwoStyle & Grace: Gianni Agnelli, “Baby” Pignatari, Alessandro “Dado” Ruspoli, 9th Prince of Cerveteri.

Part Three: The Americans

“Haven’t you ever worked?” Prince Dado Ruspoli was once asked. “No,” he responded, “I’ve never had time.” The 12 Original Playboys gallivanted within the eye of a perfect pleasure storm. They wanted for nothing because they could have seemingly anything – or anyone – thanks to a never-ending stream of old, old money.

And yet plenty of men have mighty bank accounts. These twelve seemed to have much more, like the ability to speak a dozen languages, the bravado to race Ferraris with every intention of one day wrapping one around an apple tree, and the possession of manhood that led to twelve-inch pepper grinders being named for them in Parisian restaurants.

With that in mind, it’s not surprising that only two Americans made this list.

And neither of them are named Hugh…

Howard Hughes
Howard Hughes
Howard Hughes

Howard Hughes
Nickname: “The World’s Greatest Womanizer”
Nationality: American
Occupation: Business magnate, industrialist, aviator, engineer, film producer, director, hotelier, philanthropist, CEO Trans World Airlines
Wealth: Billionaire.
Notable Women: Billie Dove, Bette Davis, Ava Gardner, Olivia de Havilland, Katharine Hepburn, Ginger Rogers, Gene Tierney, Joan Fontaine, Jean Peters
Passions: “I don’t think Howard could love anything that did not have a motor in it.” - Gene Tierny
Quotations: “I’m not a paranoid deranged millionaire. Goddammit, I’m a billionaire.”
What to learn from Howard: “Wash four distinct and separate times, using lots of lather each time from individual bars of soap.”

John F. Kennedy
John F. Kennedy
John F. Kennedy
John F. Kennedy
John F. Kennedy

John F. Kennedy
Nickname: “Prince of Camelot”
Nationality: American
Occupation: Naval Officer, Senator, President of the United States
Wealth: Kennedy estate valued at $1 billion
Notable Women: Judith Campbell, Blaze Starr, Jill Cowan, Pam Turnure, Marilyn Monroe, Gunilla von Post, Mary Pinchot Meyer, Mimi Beardsley Alford
Passions: Diplomacy, Military, Literature
Age at death: 46
Cause of death: Assassinated
Quotation: To UK Prime Minister Harold Macmillan “I wonder how it is for you, Harold? If I don’t have a woman for three days, I get terrible headaches.”
What to learn from Jack: Be a good friend and your friends will lie for you.


Last year, nearly fifty years after her clandestine affair with then-Senator Kennedy, Gunilla von Post included eleven hand-written letters and three telegrams in her book Love, Jack. While the correspondence further confirms JFK’s notorious infidelity, it also reveals his softer, more vulnerable side:

“I said [to my father] that I’d fallen in love with you, and I didn’t think I could go on the way things are now, that I wanted to end my marriage so that I could be with you. He yelled, ‘You’re out of your mind. You’re going to be president someday. This would ruin everything. Divorce is impossible.’ Then he repeated something he’s been telling us all our lives: ‘Can’t you get it into your head that it’s not important what you really are? The only important thing is what people think you are.’”

Gunilla von Post

Two years after the last telegram, as Von Post recalls in her book, she and Kennedy both attended the April in Paris Ball at the Waldorf-Astoria Hotel in New York City.

“I wanted to rush into his arms, but this was a different place and time, and discretion ruled. Nevertheless, he embraced me quickly and kissed me on both cheeks. ‘It’s marvelous to see you,’ he said, looking into my eyes. Then he turned quickly and walked through the door into a room full of a thousand people.”

Read the letters…

Part One – Death of The Original Playboy: Gunter Sachs, Porfirio Rubirosa
Part Two – Style & Grace: Gianni Agnelli, “Baby” Pignatari, Alessandro “Dado” Ruspoli, 9th Prince of Cerveteri
Part Four – Easy on the Curve: Alfonso de Protago and Prince Aly Khan
Part Five – The Party’s Over: Errol Flynn, Jorge Guinle and Don Carlos de Beistegui y de Yturbe



  • C. Brian Smith
  • C. Brian Smith