Pamela Churchill, Wartime London, and the Making of the Special Relationship

“It was very important—these Americans,” Winston S. Churchill's former daughter-in-law, Pamela Digby Churchill Harriman, recalled decades later about the perilous months of 1940–41. “If and when America came into the war, then the war would be safe. As long as they weren't in the war, it was very precarious.” And so the emissaries sent by Franklin D. Roosevelt (FDR) “were looked over very carefully. Who they were; why they were; what they were.”1 The prime minister's entire family cultivated these key Americans. In early 1941, Winston and Clementine Churchill and their daughters, Sarah and Mary, developed warm bonds with “Assistant President” Harry L. Hopkins and with Lend Lease “Expediter” W. Averell Harriman. Though Ambassador John “Gil” Winant never grew quite so close with the family, he did develop a love affair with Sarah Churchill. The most enterprising and complex of these personal/political relationships centered on Pamela Churchill. As nineteen-year-old Pamela Digby, she had wed Winston and Clementine's son, Randolph, in October 1939. The marriage soon foundered, in large part because Randolph was overbearing and gambled and drank to excess. He would spend most of the war years in the Middle East. Undaunted, Pamela nurtured close ties with her in-laws and for a while lived with them. The prime minister idolized his daughter-in-law and his grandson, who was born in October 1940 and judiciously christened Winston II. While ensconced in the family of the prime minister, Pamela, impelled by self-interest as well as affection, developed flirtatious friendships with Hopkins and with several American reporters. She juggled overlapping love affairs with Harriman, famed radio broadcaster (This is London) Edward R. Murrow, Office of Strategic Services executive and future ambassador to London John Hay “Jock” Whitney, and U.S. Army Air Force general Frederick Anderson. She would later remember, “I suddenly became very American and sort of spent most of the time with Americans.”2