Pamela Digby Churchill

March 20, 1920 — February 5, 1997

Pamela Digby grew up in the countryside in Dorset as the daughter of the 11th Baron Digby. But she aspired to more than a country life. She went up to London at the earliest opportunity, where she met Randolph Churchill. With war breaking out across Europe, he proposed to her on their first date. They were married just weeks later. The next year, she gave birth to a son. She named him after her father-in-law: Winston. Pamela and Randolph’s marriage quickly broke down. His drinking and gambling plunged them into debt. Ever resourceful, the twenty-year-old Pamela realized she was in a unique position. As the young and attractive daughter-in-law of the Prime Minister, she became one of London’s most popular hostesses in Blitz-torn London, using her position to bring rich and powerful Americans into her circle. In Pamela’s company, the Prime MInister’s associates could glean valuable information about the mindset of their still-neutral friends across the pond. But for Pamela, it was not all business. Growing up, Pamela was dazzled by the tales of her ancestor, Jane Digby, one of the greatest courtesans of the 19th century, and Pamela had a way of making men feel like the most important person in the world. One day, she met Averell Harriman, the most “beautiful” man she had ever seen. Harriman also had a daughter who was about Pamela’s age. The two women became fast friends. Soon, Pamela was spending more and more time with the Harrimans, even moving into their flat in Grosvenor Square. For Pamela, the “Special Relationship” became quite literal. When Winston Churchill asked Pamela about the rumors surrounding her relationship with Averell Harriman, she swatted it away as gossip, but it was clear it was anything but.

Photograph: Wikimedia commons, public domain (originally in Tatler)