Pamela Harriman was once called the greatest courtesan of the 20th century by her own husband, Broadway producer Leland Hayward, who made the remark to his daughter before marrying her. Decades later, Senator Edward Kennedy placed a very different tribute into the Congressional Record, describing her as “the first lady of the Democratic Party” throughout the Reagan and Bush years. When she died in Paris in February 1997 while serving as the American ambassador to France, the House of Representatives passed a resolution praising her grace, wit, and charm. No woman had ever held that ambassadorial post before her.
She was 76. Born Pamela Digby in England in 1920, the daughter of the 11th Baron Digby, she married Winston Churchill’s son, Randolph, at 19. Between that wedding and the embassy in Paris, she married twice more—first to Hayward and later to Averell Harriman, the railroad heir and Democratic statesman. In the spring of 1941, she was 21 and living in a small room at the Dorchester Hotel in a London still under bombardment.
Her husband was away at war, and his gambling debts had become her problem. Randolph had lost £3,000 gambling on a troop ship bound for Egypt—an amount that would have taken an ordinary British working man more than a decade to earn. Unable to cover the debts himself, they fell to Pamela. She sold her wedding presents, let their house, and took a job at the Ministry of Supply.
Her path crossed with Averell Harriman soon after. Roosevelt had sent the married 49-year-old to London to manage Lend-Lease supplies. Harriman also took rooms at the Dorchester. Her biographers place the start of their affair during heavy bombing that April.
She was 21; his wife was in New York. By the summer of 1941, Randolph wrote to Pamela from Cairo, joking that Harriman had spoken “delightfully” about her and that he feared he had a “serious rival. ” Randolph had no idea the affair had already begun. The relationship was handled quietly—about the only quiet thing in the whole business, as one observer put it.
Harriman’s daughter Kathleen, who was almost Pamela’s age, became her close friend and spent weekends at Chequers with her. Decades later, letters Kathleen wrote home surfaced at the Library of Congress in 2023. They never mentioned her father’s affair with her friend. On December 7, 1941, Pamela was at Chequers when word came that the Japanese had attacked Pearl Harbor.
According to Harriman’s account before the meal, the prime minister was tired and depressed, with his head in his hands. When Churchill’s valet brought in the radio news, the room looked at one another incredulously. Churchill headed for the door, announcing Britain would declare war on Japan, and the next day it did—hours ahead of the United States. Pamela was still telling that story more than 50 years later.
Randolph discovered the affair when he returned to London in the summer of 1942 after being injured in a raid in Libya. It had been an open secret for more than a year, and he blamed his parents for allowing it to run under their own roof because Harriman was useful to the war effort. The marriage was effectively over. Randolph moved out for good in November 1942.
Pamela kept her son, kept the Churchill name, and kept good terms with Winston and Clementine. After the war ended, the Americans she had entertained went home. In the late 1940s, she was linked with Gianni Agnelli, the future head of Fiat, a relationship that lasted about five years. She learned Italian and converted to Catholicism.
The relationship ended in November 1953 when Agnelli married an Italian princess. There was a spell with Stavros Niarchos, the Greek shipping magnate, and others. By 1957, when Queen Elizabeth made her first state visit to France, the British ambassador’s wife reportedly refused to put Pamela on the guest list, saying, “I will not have that tart in this embassy. ”
In 1959, Babe Paley, one of the most famous beauties in New York, arranged for Pamela to be escorted to the theater by her closest friend’s husband—Leland Hayward.
The friendship was Babe Paley’s husband Bill. Truman Capote saw Hayward and Pamela in a restaurant together that spring and knew what he was looking at. He wrote to Hayward’s wife, Slim, that summer to ask whether she knew her husband was running around with “notorious” Pam Churchill. New York divided into warring camps, with Babe Paley leading the side against Pamela and Betsy Whitney, another sister, standing up for her.
Capote wrote he was a “Slimite to the death. ” Slim told Leland she couldn’t stop him, but believed no one married Pam Churchill. She was wrong. On May 4, 1960, hours after Hayward’s divorce became final, he and Pamela married in Carson City, Nevada.
Pamela was 40. The marriage began with tragedy. On New Year’s Day 1960, Hayward’s ex-wife, actress Margaret Sullavan, died of an accidental overdose of barbiturates. That October, their daughter Bridget died of an overdose as well.
Hayward’s elder daughter, Brooke, never warmed to her stepmother and later published a bestselling memoir called “Haywire,” which portrayed Pamela coldly. Brooke also accused Pamela of keeping pearls that had belonged to her mother. Leland Hayward’s career continued through the 1960s, but the hits stopped coming and he had a series of strokes. He died in March 1971, two days before Pamela’s 51st birthday.
Her biographers agree he left her very little, with one calling her “practically broke. ”
Within months, she reconnected with Averell Harriman. His wife Marie had died the previous September. They married on September 27, 1971, a year and a day after Marie’s death.
Ethel Kennedy was one of the witnesses. Harriman was 79; she had just been widowed herself. What she married into was railroad money on a scale most people never see. She got security, and she got a country—she became an American citizen that year.
Harriman died on July 26, 1986, at age 94. His will left Pamela all his real estate and the bulk of everything else, with her cash inheritance estimated at about $33 million. His two daughters received very little, with an explanation that they were “otherwise well provided for. ” Harriman had set up trusts for his daughters and grandchildren in 1984, managed by Clark Clifford, who had advised four presidents, and Paul Warnke.
Under the management of a family office, the trusts grew from about $13 million to about $25 million—but some of that growth was borrowed. The trusts had been pledged as security for bank loans that ended up in an $18 million credit line at Morgan Guarantee. In April 1994, the heirs paid off the loan themselves, leaving their trusts down to about $3 million. In September 1994, eight members of the family sued in federal court, naming Pamela, Clifford, Warnke, and the money manager.
The complaint ran to 118 pages and put the loss at about $30 million, well over $60 million in today’s money. Pamela’s lawyer answered that she was never a trustee of those particular trusts. But a second suit, filed in Virginia, went after trusts set up by Harriman’s will on which she was a trustee, accusing her of lending trust money to herself and companies she controlled. A $20 million settlement fell apart in June 1995, and in October she sued the trustees herself.
At the end of December 1995, a settlement was announced, with terms never published. Meanwhile, Pamela had built a new life in Washington. In December 1980, after Ronald Reagan’s landslide victory, she became chair of “Democrats for the 80s,” a political action committee. Bill Clinton later said the name seemed a laughable oxymoron in those days.
She held “issues evenings” at her Georgetown home where senators, governors, and economists spoke to donors who paid $1,000 to attend. She lent the party’s House Campaign Committee $400,000 interest-free, which bought a townhouse on Capitol Hill and built a television studio later named after her and Averell. She hosted losers for 12 years through Mondale’s and Dukakis’s defeats before Bill Clinton won in 1992. She was one of the national chairs of his campaign, and at her funeral Clinton called her “the organizer, inspirer, and sustainer of the party’s long march back.
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In March 1993, Clinton nominated her as ambassador to France. She was 73 and had no diplomatic training at all—career foreign service officers must retire at 65. She presented her credentials to President Mitterrand in June. The first big file on her desk was a world trade deal France was fighting over farm subsidies and American films.
She faced an American intelligence scandal in early 1995 when France asked five Americans to leave the country. She fought for dull things as well, including upgrading State Department computers. In June 1994, she stood with Clinton on the beaches of Normandy for the 50th anniversary of D-Day—50 years earlier, she had spent the invasion summer in London among American officers. On the evening of Monday, February 3, 1997, she went swimming at the health club of the Ritz Hotel in Paris.
She suffered a stroke at the pool. She was taken to the American Hospital and never regained consciousness. She died on Wednesday afternoon, February 5, at 3:48, with about 10 members of her family at her side. About 40 minutes later, Clinton spoke at the White House, saying America had lost “a great public servant and another immigrant who became a great American.
” Three days later, President Chirac raised her to the highest rank of the Legion of Honor, the Grand Cross, saying that seldom since Benjamin Franklin and Thomas Jefferson had America been so well served in France. Her funeral was held at Washington National Cathedral on February 13, and she was buried beside Averell at Ardan. Her son and his family were left facing about $12 million in estate taxes and $2 million more owed to Averell’s heirs under the settlement. In May 1997, Sotheby’s sold more than 6,000 objects from her homes in Georgetown, Middleburg, and Paris for $8.
7 million, including a Van Gogh of white roses she had given to the National Gallery in 1991 and then borrowed back for her residence in Paris. Her papers went to the Library of Congress—about half a million items. The State Department’s page on her gives her dates in Paris and notes she wasn’t a career diplomat. The last line reads: “Died at post on February 5, 1997.
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