Pamela Digby Churchill Hayward Harriman

The Ultimate Courtesan


Churchill’s Confidante

Pamela Churchill
Pamela Churchill

Randolph Churchill, son of the future prime minister, would change Pamela Digby’s life forever. Randolph was just what Pamela was looking for; hot-shot journalist, man-about-town and a budding politician in his own right, he whisked Pamela off to The Ritz for a night of dinner and dancing. By the end of the evening, Randolph had proposed to her and Pamela had accepted.

On the 4th October 1939, three weeks after their first date, Randolph and Pamela were married to the horror of of Pamela’s friends who had warned her that Randolph was trouble.

Randolph was a womaniser, he drank too much, he gambled too much and he was a very difficult person. Michael Dobbs, author of Churchill’s Hour says “Pamela knew that once she had the name Churchill she had something that was going to last for the rest of her life”.

By May 1940, it was clear that Winston Churchill was the man of the hour. With German tanks rolling through France and the British army in full retreat, Prime Minister Neville Chamberlain fell on his sword. The task of steeling Britain’s nerve through its darkest hour now fell to Churchill.

In August 1940, Pamela Churchill cemented her ties with the most illustrious family in Britain by producing a health baby boy.

The son would carry the name Winston in honour of the great man himself. Pamela Digby would always be a Churchill now. She was about to become more useful to Winston than either of them could have imagined.

By early 1941, American war aid was flooding into Britain but, despite his show of bravado, Churchill knew American aid alone would not be enough and although she didn’t know it, Pamela was about to play a crucial role in her father-in-law’s plans.

Averell Harriman
Averell Harriman

With President Roosevelt wavering, Churchill targeted the President’s top man in London, Averell Harriman, for special attention. He was a very handsome, hugely wealthy man, whose family owned Union Pacific Railroad. If he could gain Harriman’s ear, Churchill would gain a direct route to Roosevelt’s inner circle. A glittering dinner was laid on for the American at the Dorchester Hotel and Churchill had the perfect escort to make him feel welcome.

During the dinner there was an air-raid. Averell was very taken with Pamela Churchill and invited her to his room rather than going to the bomb shelter which began a rip-roaring wartime affair. Pamela had launched out on her very own special relationship and it was one that would tie Roosevelt’s man, intimately, into Churchill’s sphere of influence. It was the start of an extraordinary relationship that was very useful to Winston. Pamela would routinely report back with Harriman’s views.

Edward R. Murrow
Edward R. Murrow

In the spring of 1942, Randolph returned home on leave. With Pamela’s affair with Harriman the talk of the town, her cuckold husband lashed out accusing Winston of encouraging the liaison. Pam’s affair would signal the end of her brief marriage.

In December1941, Winston Churchill finally got his wish. The US would now be fighting shoulder to shoulder with Britain and Churchill made sure the onerous duty of looking after the high-ranking Americans, who poured into London, fell to Pamela.

The broadcaster  Edward R. Murrow wasn’t the richest American in town, but his nightly reports from the rooftops of bomb-torn London made him the most glamorous. With Murrow, Pamela discovered something new within herself; the ability to love.

In the spring of 1945, while the allies gave thanks for the victory in Europe, Pamela and Edward began to celebrate their own happy day. Murrow had proposed, a liaison destined to fail as when Murrow returned to the States to arrange a divorce from his current wife, he discovered she was pregnant with their first child.

Gianni Agnelli
Gianni Agnelli

In the spring of 1947, Pamela, moved to Paris; the finishing school for the courtesan. Now divorced and still only 27, Pam was free to throw herself into the liberated world of post-war Europe and the most eligible playboys were soon bidding for Mrs Churchill’s special favours. Pamela would devote the next twelve years to perfecting the silky skills of seduction.

By chance, she met Gianni Agnelli, heir to the Fiat Motor Company. Agnelli was one of the richest men in Europe with a string ofluxury homes from St Moritz to St Tropez. Gianni Agnelli was the archetypal playboy with a taste for fast cars and high-stakes gambling. Pamela would devote five precious years to luring the so-called uncrowned King of Italy to the altar. But is marriage was a business transaction for Pamela, it seemed the art of closing the deal had deserted her. Gianni was catholic and Italian, Pamela was neither. Gianni dumped her despite her being pregnant. He insisted she have an abortion which was carried out in Switzerland.

Pamela had notched up over a decade as Europe’s top good-time girl, but what had begun as an escapist paradise was fast becoming a dead-end. At nearly forty and in danger of becoming a laughing stock among the European jet-set she fled, in 1959 to New York in search of her own American Dream.

Leland Hayward
Leland Hayward

Within a matter of days, Pamela had homed in on her next jackpot, the legendary Broadway producer Leland Hayward. With five marriages already to his name, not to mention affairs with Greta Garbo and Katherine Hepburn, there was no doubting Hayward’s taste fro romance. With his latest marriage on the rocks, Hayward was ripe for plucking. On the 4th May 1960 at a quickie wedding chapel in Nevada, Pamela Churchill finally closed a deal. After a honeymoon in Vegas, Pamela threw herslf in into her new role as the ultimate English trophy wife.

Pamela Churchill would devote the next ten years to pampering her workaholic husband, but she was also taking good care of herself. Pamela had extremely expensive tastes and was burning her way through her husband’s fortune and was determined to protect it from the attentions of his family.

In February 1971, Leland suffered a massive stroke and was rushed to hospital where he died four weeks later. The family gathered for the reading of the will and were horrified to find that the fortune had gone!

In March 1971, the day after the funeral of her second husband, Pamela made contact with Averell Harriman. Averell was now 79 years old, richer than ever and recently widowed. 30 years after their wartime romance, Pamela and Averell picked up where they left off. In that time Averell had been American Ambassador to the Soviet Union, a presidential candidate, Governor of New York and confidante to JFK. Just six months later they were married. Pamela had finally found a husband with a wallet to match her lavish taste.

With Harriman on her arm, Pamela Churchill set about transforming their Georgetown home into Washington’s greatest political salon. With Pamela as choreographer-in-chief cash was soon flooding in to the Democratic Party chest ready for the next presidential race.

Pamela Churchill would use her communication skills, contacts and womanly wiles to help boost the coffers of the new candidate and her support and popularity would help Arkansas would-be governor, Bill Clinton, to a landslide victory. In return for this, Clinton repaid her by making Pamela US Ambassador to France and by 1993 she was back in Paris not as a courtesan but as a woman of substance.

Further Reading

[amazon asin=0007183054&template=add to cart] Churchill’s Hour – Michael Dobbs

[amazon asin=0684809508&template=add to cart] Reflected Glory: Life of Pamela Churchill Harriman -Sally Bedell Smith

[amazon asin=0751513490&template=add to cart] Life of the Party: Biography of Pamela Digby Churchill  – Christopher Ogden

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