In the winter of 1941, in a blacked-out London under nightly bombardment, a twenty-one-year-old woman sat across a dinner table from the richest and most important American in Britain. Her husband was three thousand miles away in the desert. Her father-in-law was the prime minister. The man holding her gaze controlled the flow of guns, ships, and food that were keeping Britain alive.
Within weeks, she was his lover, and the affair was conducted so openly that the whole of Downing Street knew and chose to say nothing. Pamela Beryl Digby was born on March 20, 1920, at Farnborough in Hampshire, the eldest daughter of Edward Kenelm Digby, the 11th Baron Digby, master of Minterne, a handsome house set in the green folds of Dorset. The family name was ancient, but the money was thin. That gap between the title on the gate and the figures in the ledger shaped her from the beginning.
She grew up in the conventional rhythm of the interwar rural gentry, learned to ride almost before she could read, and was sent abroad to be finished in Paris and Munich. In 1938, she was presented at court as a debutante. There was, however, a problem, and Pamela saw it early. She was not beautiful.
In a world where a girl of small fortune was expected to trade on her looks to marry well, she had been handed a modest hand of cards. Instead of settling for a quiet county marriage, she found the one card she did hold and learned to play it better than anyone alive. She made every man believe he was the only one. She listened as though the man in front of her were the single most fascinating person who had ever spoken.
She remembered the details of his work, his worries, and fed them back with a warmth that felt entirely genuine. Charm of that kind functioned in her like a craft, practiced and refined and aimed. She understood that in a world run entirely by men, the woman who could command a powerful man’s attention held a sliver of his power in her own hand. In the first week of September 1939, with the country sliding into war, she sat down to dinner beside Randolph Churchill, the only son of Winston Churchill, then First Lord of the Admiralty.
Randolph was twenty-eight, handsome in a heavy way, brilliant in flashes, and already marked by the drinking and recklessness that would ruin him. Seized by the urgent thought that he might be killed and ought to father a son to carry the Churchill line, he had proposed to a string of women that autumn. Pamela said yes. They were married on October 4, 1939, at the Church of St.
John in Smith Square, Westminster, one month and one day after Britain had gone to war. She was nineteen. She was not in love with him, but she understood with great clarity what the marriage offered. It offered the name.
The marriage itself began to disappoint almost at once. Randolph drank heavily and gambled with pathological recklessness. As he went off to his regiment, Pamela was drawn into the heart of the Churchill family at the precise moment it became the heart of the nation. When Winston Churchill became Prime Minister in May 1940, his daughter-in-law was already installed within his orbit, a fixture at the family gatherings.
She dined at Downing Street and spent weekends at Chequers while the fate of the war was decided in the rooms around her. On October 10, 1940, she gave birth to a son, named Winston after his grandfather. The birth of a male Churchill heir secured her place in the family beyond any question. Underneath the surface, the marriage was disintegrating.
Sent abroad on service, Randolph ran up gambling debts on the very voyage out, then wrote home instructing Pamela to settle the accounts. One demand was for around $12,000, a fortune in those years, and Pamela had no means of paying it. Rather than expose her husband’s recklessness, she protected the family name and shouldered the problem herself. She took a paid job at the Ministry of Supply, quietly sold the wedding presents and a good deal of her jewelry, and moved the baby to the countryside for safety, all while keeping the scale of the debts a secret from his parents.
In March 1941, a tall, grave, immensely rich American stepped off a plane into wartime London carrying the power to keep Britain in the war. His name was William Averell Harriman, the personal envoy of President Franklin Roosevelt charged with overseeing Lend-Lease, the vast flow of weapons and supplies that Britain could no longer pay for. He was the most important American in the country. Without the supplies he controlled, Britain could not fight.
Harriman was forty-nine, the son of a railroad baron, reserved, serious, and married to his second wife, who was three thousand miles away. Churchill courted him with everything the British had, dining him, taking him to Chequers, bringing him inside the family circle. To keep Harriman happy and engaged was a matter of national survival. It was in this atmosphere of careful hospitality that Harriman was introduced to Pamela Churchill.
She was the most attentive young woman in London, schooled in the art of making a great man feel he was the only one, seated beside the most important American in the country. The chemistry was almost inevitable. Within weeks, they were lovers. The affair was extraordinary not because it was secret but because it was not.
They were seen together, known to be together, and the Churchills themselves said nothing and did nothing. The Prime Minister of a country fighting for its survival had decided that the comfort and goodwill of the American envoy mattered more than the propriety of his daughter-in-law’s behavior. Harriman, happy and emotionally bound to Britain, was worth more than Randolph’s wounded honor. Some who knew her well came to believe that Pamela was not only Harriman’s lover but Churchill’s most useful private channel to the Americans.
She spent her nights with the man who controlled the flow of American supply and knew the mind of the Roosevelt administration, and her days inside the Churchill family. What cannot be proven is the precise content of what passed between them, but the circumstances are suggestive. Pamela was an extraordinary listener, the kind of woman to whom men talked freely. She was learning in the most direct way possible that intimacy with powerful men was itself a form of power.
When Harriman’s duties carried him away from London, the war kept bringing other powerful Americans to her door. There was Edward Murrow, the celebrated broadcaster whose nightly reports had brought the courage of the bombed city into millions of American homes, whose relationship with Pamela shook his marriage to its foundations. There was William Paley, the founder and chairman of the Columbia Broadcasting System, drawn within her circle. And there was John Hay Whitney, known as Jock, heir to one of the largest fortunes in the United States.
Three men, three empires of money and influence, and a single Englishwoman of twenty-four with no fortune of her own who had drawn all three into her orbit within the space of a few wartime years. Randolph, returning from his service, learned of his wife’s affairs, and the discovery enraged and humiliated him. The divorce came in 1945, and Pamela kept two things from the marriage that would matter for the rest of her life: her son and the name Churchill. In the late 1940s, she left England with its rationing and its gray austerity and moved to Paris.
In London, she was Randolph’s discarded wife. In Paris, she could be whoever she chose to be. She arrived with very little money and a great deal of nerve, and the city was full of wealthy and powerful men. For roughly five years through the early 1950s, she was the companion of Gianni Agnelli, the grandson and heir of the founder of Fiat, the most glamorous man alive.
She would later call these the happiest years she ever knew. But Agnelli, for all his devotion, would not marry her. In 1953 he married an Italian princess, and Pamela was left with nothing but the memory. After Agnelli came Baron Elie de Rothschild, a partner in the family bank and a master of Chateau Lafite.
He was married, and a Rothschild did not divorce his wife to marry a divorced and somewhat notorious Englishwoman. Pamela pressed the point and received the answer she had heard before. He would not leave his wife. A second great relationship ended on exactly the rock that had wrecked the first.
The lesson was inescapable. As long as she pursued men already attached, she would remain forever the companion and never the wife. She resolved never to be refused a third time. At the end of the 1950s, in New York, she found a man who would actually marry her.
Leland Hayward was one of the most successful theatrical and film producers of his era. He divorced his wife, an episode that earned Pamela a fresh wave of hostility, and in 1960, he married her. For eleven years she was Leland Hayward’s wife, and by the accounts of the period, it was a successful and even happy marriage. Then, in 1971, Leland Hayward died.
Within six months, Pamela married the man she had taken as a lover thirty years before in a blacked-out London. Averell Harriman had gone on to a towering public career as ambassador, commerce secretary, governor of New York, and elder statesman of the Democratic Party. His wife had died, and he was a widower in his late seventies. The old lovers, both now free, decided to marry within a matter of weeks.
Through him, Pamela gained American citizenship and access to one of the great American fortunes. She became the wife of a revered elder statesman, and through him she was drawn ever deeper into the world of Democratic politics. Averell Harriman died in 1986 at the age of ninety-four, leaving Pamela a very rich widow and plunging her into a bitter battle. The Harriman children and grandchildren launched a long and savage legal war against her, accusing her of mismanaging and draining the family money.
The litigation dragged on for years, costly, public, and damaging. Yet even as the inheritance battle raged, Pamela was building something the Harriman heirs could never take from her: a position of real and independent power in American politics. In 1981, she founded a political action committee called Democrats for the ’80s, known to everyone as Pam PAC. From her estate at Middleburg, Virginia, she set out to raise money and rebuild the party’s fortunes.
She turned out to be magnificent at it. The same gifts that had drawn wartime envoys and Italian heirs now drew donors and politicians to her dinners. In its first twenty months alone, the committee raised more than a million dollars, and over its life it is credited with raising on the order of ten million. The crowning achievement came with the rise of Bill Clinton, whom she backed early and importantly.
When Clinton won the presidency in 1992, he remembered his friends. In 1993, he appointed Pamela Harriman the United States Ambassador to France. The Baron’s daughter from Dorset returned to the city of her great love affairs, not as a kept companion, but as the official representative of the most powerful nation on Earth. On a day in early February 1997, Pamela Harriman, then seventy-six, went to swim her laps in the indoor pool of the Hotel Ritz in Paris.
It was there, in the water, that she suffered a sudden cerebral hemorrhage. She was pulled from the pool and rushed to the American Hospital at Neuilly, and there the following day she died. The president of France, Jacques Chirac, came in person and laid upon her flag-draped coffin the Grand Cross of the Legion of Honor, the highest order France can bestow, an honor never before given to a woman serving as a foreign diplomat. President Clinton sent Air Force One across the Atlantic to bring her body home.
Her funeral was held at the National Cathedral in Washington, and the powerful of American public life gathered to mourn her. The argument over who she had really been began at once. To her detractors, she was a courtesan who had slept her way from a Dorset barony to a Washington Cathedral. To her admirers, she was the cleverest political operator of her generation, a self-made woman who had risen through the only door history left open to her.
She had no money, no great beauty, and no power the world would recognize. She had only attention and the will to spend it. And with those two things alone, she rewrote the whole of her own ending.