Pamela Digby was born into the peerage of Great Britain, but she spent 20 years of her life as a courtesan - mistress - a kept woman. She was feminine, flirtatious, and maternal to men and made them - and her select women friends - feel special. Wives worried about their husbands around her. She changed her man and her life many times but she loved to be surrounded by powerful people. She was highly criticized and judged from her earliest days as a society girl but if she knew it she pretended not to or didn't let it get her down. She was a "bad girl" and yet to her funeral came those with prestige and power.
Randolph Churchill, the son of Winston Churchill of World War II fame, asked her to marry him the first date they had, an arranged date, and had asked many women before who turned him down. She said yes and was married to him before he went off to war. She quickly became pregnant and bore him a son - an heir, named Winston. He would be her only child.
Pamela's family had an old title and prestige if not money. Her education was not substantial. They couldn't afford the best schools for her. But they sent her to France to board with a family that took in girls like her and showed them around to absorb the culture. Who knew that in her later years she would become the United States Ambassador to France after having lived as a mistress in that country.
At the age of 17 her education had ended. She was "finished." But she went to the Coronation of King George VI, who took over the throne when his brother The King Edward VIII abdicated his throne to be married to Wallis Simpson. Who knew that someday she and Wallis, who was a good 20 years older than she, would become good friends.
Pamela Digby made her debut in front of the Queen in 1938, wearing clothes that were not much compared to most of her more wealthy peers, clothing that embarrassed her. But she still attended a marathon of parties, races, and entertainments designed to show off aristocratic girls ready to marry and breed with wealthy young men. More than 1000 girls debuted that year and most of them left the city and went back home to the country to wait on marriage proposals. The others stayed in the city. Maybe a hundred girls were considered popular. Not Pam. That same year Kathleen "Kick" Kennedy and her sister Rosemary, daughters of Joseph Kennedy, the United States Ambassador to Britain, and father of the future American President John F. Kennedy, called her dumpy. As it turned out, she and Kick would have an enduring friendship.
Pamela's father won a substantial amount of money at the horse races that allowed him to afford her a Jaguar car, if not the ability to give her a fancy dress ball like other girls. He rented a place in Mayfair, London, to put her in the right neighborhood. But she was taken under wing by her mother, who never failed to have confidence in her, and some of her mother's friends. One, Olive Baille, invited her to house parties where she had famous Hollywood stars on the guest list. Clearly she had something going for her.
Pamela did get an inheritance that would have allowed her to be independent, so long as she budgeted, but she wanted more. Fulke Warwick (ie. of Warwick Castle fame) may have been her first lover. But she claimed only a dinner while he dined out on stories of being sexual with her. Debutantes were thought to be virgins. Most of them were chaperoned.
And so she went through a second season, 1939, as did many girls still in need of a husband. She went to a pre-war ball at Blenheim Palace - the home of Winston Churchill's family - that was given by the Duke and Duchess of Marlborough for Lady Sara Spencer - Churchill. (Are the names sounding familiar?) But she was set up on a blind date with Randolph Churchill.
On October 4, 1939 they married. The smiling bride wore a coat with a fur collar, not the typical white wedding dress, while the smiling groom wore his military uniform. She now had the Churchill name, so respected, and would carry it all her life. Randolph, by many accounts, was obnoxious and probably alcoholic. By January 1940 she was pregnant. He was in the Fourth Hussars. She had to live alone and went from one friend's accommodations to another. (I know, you're wondering what about the Palace?) They were totally incompatible and unhappy but then people thought Randolph as difficult. She was 20. He was 29. Like many wives, Pamela got involved in the war effort and became something of a tour guide, guiding American officers in London. Her ability to organize and plan large and small events would be useful in all her relationships.
By the time Randolph returned after almost a year away, Pamela acted excited and happy to see him and introduced them to their son, Winston, for the first time. But she had already met and had an affair with another man who would figure in her life, William Averell Harriman.
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