Romantic Involvements and Affairs
Beside two additional marriages, Pamela Harriman had numerous affairs with men of prominence and wealth. During her marriage to Randolph Churchill, she had romantic involvements with men such as: Averell Harriman, who much later became her third husband; Edward R. Murrow; and John Hay "Jock" Whitney. Notable consorts after her divorce included Prince Aly Khan, Alfonso de Portago, Gianni Agnelli, and Baron Elie de Rothschild.
Churchill became well known for her attention to detail with men. When involved romantically with a man, she paid extremely close attention to his desires, his preferences, and went to any lengths necessary to satisfy his needs during the affair. William S. Paley, briefly a consort during the war, said: "She is the greatest courtesan of the century", meaning it more as a compliment than a detraction. According to Max Hastings, "she was unkindly described as having become 'a world expert on rich men's bedroom ceilings'."
After her divorce from Randolph Churchill, she moved to Paris and in 1948 began her five-year-long affair with Gianni Agnelli. She described this as the happiest period of her life. Agnelli, however, was not faithful in this relationship. In 1952, Pamela found him with a young woman, Anne-Marie d'Estainville, and threw a rare fit about this. Agnelli sustained a severe leg injury in a car accident while bringing d'Estainville home. Pamela nursed him through his injury, and later became pregnant (although it was never confirmed that this was by Agnelli), but had an abortion in Switzerland. Later, Princess Marella Caracciolo di Castagneto became pregnant by Agnelli, and Pamela Churchill ended the affair.
Her next significant relationship was with Baron Elie de Rothschild, who was married. He supported her financially, and she was schooled in art history and wine-making during this clandestine and short relationship. During this time she also entertained an affair with the writer Maurice Druon and with the shipping magnate Stavros Niarchos.
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