Pamela was born on March 20, 1920, to Constance “Pansy” and Baron Kenlem “Kenny” Digby, a minor noble in Dorset in southwest England. They lived in a mansion called Minterne. Although they had a noble title, the family was facing money struggles following World War I, and they sold off most of their other property and valuables. Nevertheless, they maintained a large staff.

Pamela was the eldest daughter of four children. Her parents were content with their rural lifestyle and did not often travel to London. Pamela was largely raised by nannies and had little contact with her father, Kenny. As a child, Pamela was intrigued by the scandalous history of her ancestor, Jane Elizabeth Digby, who led an adventurous life in the 19th century, eventually marrying Sheikh Abdul el Mazrab. Pamela longed to follow in her ancestor’s footsteps.

At age 15, Pamela and her sister Sheila were sent to the Downham boarding school, where she was quickly made a prefect. It was Pamela’s first opportunity to spend time with girls her own age. Pamela had a poor education and was not a good student. She soon left with only a certification in “domestic science.” In 1937, she was sent to stay with Countess von Harrach, a Habsburg, in Munich for “finishing” (further refinement). She was shocked by the rise of antisemitism she saw there. Pamela has claimed she met Hitler while in Munich, but author Purnell suggests this might have been an exaggeration.

That autumn, her father took Pamela traveling in North America, where she met George McCullagh, owner of the Globe and Mail, who courted her and published a picture in the paper of her horseback riding during a hunt to flatter her. Pamela found the trip “a revelation.”

During the winter of 1937, Pamela prepared for her “coming out”—a formal introduction to London’s upper-class society to find a husband. During this time, Pamela became close with Lady Olive Baillie, who “shared her fascination with power […] and powerful men” (23). In April 1938, soon after Hitler invaded Austria, Pamela attended her debutante ball, where she was introduced to the king and queen. Pamela felt self-conscious about her “chubby” figure, freckles, and relatively cheap dresses compared to the other girls. Kathleen “Kick” Kennedy, sister of future President John Kennedy, who also attended the balls that Season in London, described her as a “fat, stupid little butter ball” (26). Pamela became friendly with Clarissa Churchill, niece of Winston Churchill. However, Pamela failed to find a husband during the Season.

Tensions between Germany and the other European powers, including the UK, continued to heat up. Pamela’s father was dismayed by MP Winston Churchill’s bellicose language calling for war with Germany rather than appeasement, which was Prime Minister Chamberlain’s policy.

Upon returning to Dorset after her first Season, Pamela enjoyed exercising her freedom by driving her Jaguar around the countryside with a chaperone. At 18, she convinced her parents to allow her to travel to Paris. There, she met Rosamund Fellowes, who invited her to the French Riviera. Pamela’s “red hair and milky skin” (30) was popular with men there, but she was forced to return to Britain due to the threat of invasion from Germany.

Pamela became friends with Kick Kennedy, whose father, Joe Kennedy, was the US ambassador to the UK. It was an open secret that Joe had sexually assaulted several young women, and it was widely suspected that he had sexually assaulted Pamela, although she never spoke of it publicly. Joe was also disliked for his support of the Nazis.

As the next Season began, there was increasing pressure for Pamela to get engaged. She was often hosted by Lady Baillie, who taught Pamela how to become a hostess and cultivate relationships with important and powerful men. Pamela also increasingly went out to gamble and party with wealthy men like the Earl of Warwick, which earned her a “reputation” as a “fast” woman, although it was “not quite the reality” (37).

On September 3, 1939, the UK declared war on Germany.

Pamela got a job in London as a French translator for the Foreign Office. One day, Randolph Churchill, a notorious misogynist and heavy drinker, called Pamela and asked her to go to dinner with him, although they had never met. Pamela agreed. She found him a bore, but when he proposed to marry her over dinner, she agreed, “beguiled by the chance to marry into a political family” (40). Her friends and family tried to get Pamela to change her mind, but she refused. Randolph was constantly searching for a woman who would give him the unconditional love he felt Clementine, his mother, had withheld from him.

On October 4, 1939, Pamela and Randolph married in London and honeymooned in Lincolnshire. The night after their wedding, Rudolph spent hours reading aloud from Gibbon’s Decline and Fall of the Roman Empire instead of having sex with his wife. The new couple was invited to dine with Lord Max Beaverbrook, owner of newspapers like the Evening Standard. Pamela quickly charmed Max.

Rudolph was in the military. His regiment was stationed in Beverley, East Yorkshire. Pamela followed him there. It was widely believed that Randolph had been “spoiled” by his father, Winston Churchill, and was not suited to combat missions. Randolph was rude and belligerent at dinner parties while drinking, embarrassing Pamela. He was frequently absent and had affairs with other women. He spent beyond his means buying gifts for them, in addition to drinking and gambling. Nevertheless, there was pressure for Pamela to get pregnant. Pamela grew close with Clementine and Winston Churchill, her in-laws, and Randolph was jealous of her relationship with them.

Rumors about the state of Pamela’s marriage circulated widely. When she became pregnant, she moved in with the Churchills at Admiralty House. Pamela had a difficult pregnancy, suffering from hyperemesis gravidarum (severe nausea and vomiting). The Churchills’ home was the heart of the preparations for war against Germany. They trusted her discretion more than that of her husband.

On May 10, 1940, Chamberlain resigned, and Winston Churchill became Prime Minister. Pamela moved in with the Churchills at 10 Downing Street. She mixed socially with members of the Labour Party for the first time. As London and the rest of England prepared for war, Pamela observed how Clementine, the prime minister’s wife, influenced and managed his moods and fits of pique. Pamela attended a lunch they hosted for General Charles de Gaulle and charmed him. She became a regular at Churchill political gatherings. Randolph was incensed at her “rising star.” His drinking worsened. 

On September 7, 1940, the bombing of London, known as the Blitz, began. Because of the danger, Pamela eventually moved to Chequers, the prime minister’s country home. On October 6, in the midst of nearby bombing which shook the house, Pamela gave birth to her son, Winston.

Neither Pamela nor Randolph was a doting parent to the infant Winston. Randolph was sent to a training camp in Scotland and eventually sent to Egypt. Meanwhile, Pamela became part of a diplomatic campaign to convince the United States to contribute to the war effort. She was photographed as an ideal British mother for Life magazine as part of this effort. Randolph and Pamela’s relationship continued to sour.

The UK desperately needed the isolationist United States to support its battle against the Axis. Pamela was tasked with seducing and convincing the US envoy, Harry Hopkins, to support them. Faced with her husband’s mounting debts, she asked Evening Standard owner, Max Beaverbrook, for financial support. He effectively hired her as an informant or spy in exchange for helping her financially. Pamela moved to London, feeling free for the first time in her life. When she miscarried during her second pregnancy, she was “almost certainly” relieved.

Purnell notes that, during the war, London was “the sexiest city in the world” (81). Conventional rules around sex went out the window as the threat of death hung over the city due to the Blitz. Pamela became accustomed to the constant bombings. She enjoyed the thrill of the parties in the city.

Staid American statesman Averell Harriman was sent to the UK to manage the Lend-Lease program, through which the UK leased munitions from the United States. Pamela was set to seduce the married, “Victorian” man to convince him to agree to terms friendly to the UK. Harriman was struck by her beauty as well as her intelligence. Soon after he arrived, during a particularly intense bombing campaign, they began an affair. Max Beaverman was “ecstatic.”

Pamela was useful as a liaison between the UK and US officials, as each was historically skeptical of the other party. She was also essential in convincing Harriman of the importance of supporting the UK war effort.

Winston and Clementine Churchill were aware of and even supported Pamela’s affairs insofar as they were in service of the war effort. They also understood, given their son’s notorious behavior.

Averell’s daughter Kathleen (known as “Kathy”) arrived in London and “provided cover” for Pamela’s affair with her father. Kathy introduced Pamela to Edward “Ed” Murrow, a CBS news anchor who reported from London throughout the war. Meanwhile, in Cairo, Randolph imperiled the war effort with his loose talk to sex workers while drunk, causing a minor scandal.

Randolph was sent with Averell to tour North America while Pamela and Kathy stayed in London, entertaining the troops. Kathy grew increasingly jealous of the attention Averell gave Pamela. Randolph was eventually sent back to Cairo as “director of propaganda” (96). Pamela corresponded with President Roosevelt to encourage him to commit US military assets to the war. He was intrigued by her. On December 7, 1941, Japan attacked Pearl Harbor, and the US entered WWII. Pamela and the Churchills were relieved.

Pamela’s public profile continued to increase. She hoped the good press would help Churchill, who was facing a no-confidence vote. When Rudolph returned to England on leave, he and Pamela continued to argue about money and other concerns. He expected her to be entirely obedient, and she loathed him. Churchill arranged for Rudolph to be sent back to Cairo on March 26, 1942, but Pamela was persuaded to put off getting a divorce. After Rudolph left, Pamela moved in with the Harrimans in London. Rudolph was injured in a raid in Benghazi in May 1942 and sent back to London, obliging Pamela to move into another apartment. Randolph was verbally and physically abusive to his wife. He also quarreled with his parents.

Word about Pamela’s affair with Averell spread in the press. Averell’s wife, Marie, a respected collector of Impressionist and post-Impressionist paintings, was furious. Averell was sent to Moscow. He directed his daughter to end the affair on his behalf.

After Harriman left, US Colonel Jock Whitney moved into his apartment. Pamela began an affair with Jock, and they became friends. She set up house with young Winston at 49 Grosvenor Square, dubbed “the Attic.” She held regular parties for important men to gather information. She also began an affair with Ed Murrow. A lifelong liberal, he encouraged Pamela to “question the tenets of the Conservative Party” (113) and promoted concepts of racial equality. Pamela hoped he would divorce his wife, Janet. However, Ed often grew jealous of the other people with whom Pamela was having affairs, such as Ed’s boss, Bill Paley.

Young Winston was often neglected between his mother’s work and his father’s dependence on alcohol. Purnell notes that Pamela frequently had periods of unexplained illness during this time. She speculates Pamela may have had illegal abortions to protect her way of life and her work.

Churchill often used Pamela to charm American military leaders into supporting British wartime tactics. Purnell argues that her diplomatic efforts helped create “the Special Relationship” between the UK and the US (123).

On June 6, 1944, Allied troops landed in Normandy on D-Day. Although this was an important day in the war, it marked the beginning of the end of Pamela’s usefulness to the war effort. She had succeeded in her mission to get the US to contribute to the fight against the Axis.

Bombings of London continued. Rudolph came back to England and argued violently with his parents, largely about Pamela. In an attempt to smooth things over, Pamela met with Randolph for lunch and asked for a divorce. He agreed.

Pamela briefly went to Paris and enjoyed the respite from the war. She returned to a London threatened by supersonic V-2 bombs. Like the British public, she grew frustrated with Churchill’s management of the stalled war effort. Due to the impending divorce, she was not invited to the Churchill family Christmas celebrations.

Ed Murrow continued to stall his promised divorce from his wife, Janet, and Pamela became frustrated. She also continued her correspondence with Averell. Both she and Averell felt it was important to keep open diplomatic relationships with the USSR.

Meanwhile, Winston was being raised in London by the housekeeper, Mrs. Marion Martin, and Pamela felt lonely in London. She considered political office but felt it was too difficult, as there were few women in politics. Churchill lost the election on July 26, 1945. World War II ended on September 2 of that year.