..’One unwelcome reminder of JFK’s torrid affair with Marilyn — the affair that most troubled Jackie — arrived on her doorstep in the form of another blond bombshell by the name of Madonna. Already a pop icon, Madonna was best known at the time for her “Material Girl” video, an homage to Monroe’s “Diamonds Are a Girl’s Best Friend” number from the film Gentlemen Prefer Blondes.
The Material Girl and JFK Jr. met briefly at a party following one of her concerts at Madison Square Garden in 1985. Three years later, after the breakup of her stormy marriage to Sean Penn, she went after John. Beyond the obvious — stories of her sexual escapades abounded — Madonna was convinced that destiny was taking a hand in bringing together the undisputed heiress to Monroe’s platinum persona with the son of JFK. She told friends she believed that her affair with JFK Jr. would be nothing less than “cosmic.”
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