Kick Kennedy & Pam Churchill : A Fateful, Dynastic Friendship Between Two Daughters of the Two Famous Families
Kathleen “Kick” Kennedy, the favorite sister of future U.S. president John F. Kennedy, and Pamela Churchill, the daughter-in-law of British Prime Minister Winston Churchill, enjoyed one of the closest relationships between the two world famous families -- one filled with passion, politics, humor and ultimately tragedy. This is an excerpt from “When Lions Roar: The Churchills and the Kennedys” by Thomas Maier.
Winston Churchill and wife Clementine with Kathleen “Kick” Kennedy during 1946 Florida trip. Credit: JFK Library.
After the war, Kick Kennedy and Pamela Churchill’s friendship grew closer. They were no longer vaguely familiar debutantes with little in common but rather an American widow and British divorcée, both in their mid-twenties, whose experiences and social circles in war-torn London had bonded them together.
With her family in America, Kick still maintained the good-girl veneer that her mother insisted upon. On her own in London, she’d become more independent-minded, especially after the death of her husband Billy Hartington during the war. Though she didn’t approve of every adulterous move by Pamela, Kick appreciated the other woman’s spirited, devil-may-care approach to life. For all the friendship and favors Pamela Churchill provided in London, Kick Kennedy felt compelled in 1946 to invite her for an extended wintertime vacation in Florida. Kick “was my close friend and that’s how I came into the Kennedy family,” Pamela recalled decades later. “The first time I ever came to America, I stayed with the Kennedys down in Palm Beach.”
As an honorary Kennedy, Pamela found herself enthralled by the family’s dinner table conversation about politics. She went shopping with Rose Kennedy and appeared in the local newspaper columnist’s list of “Best Sundressed Women in Palm Beach,” even though she appeared “quite pale when near the other deeply tanned beauties.” With Kick and her parents, Pamela also enjoyed the Sunday races at Hialeah. After enduring so many wartime hardships and material restrictions in England, Pamela was amazed by the extravagant wealth and undisturbed beauty of America.
When the former prime minister arrived in Florida, Kick joined the Churchills as part of their entourage. She rode with them in a special car, escorted by twenty policemen on motorcycles, to the Orange Bowl stadium, where they watched Winston receive his honorary degree from the University of Miami. Afterward, Kick joined the Churchills at the Surf Club. Under a cabana at this private resort, Winston took out his oils and composed a painting of the endless blue-green Atlantic and darkened clouds on the horizon giving way to daylight. On this warm afternoon, the Churchills brought along their bathing suits and decided to go for a swim. “Winston presented a very comical sight, bobbing around in the surf,” Kick wrote in her diary. “He adores the water though I must say I wouldn’t enjoy swimming in such a public spot every day.”
As they entertained themselves at the Surf Club, Kick laughed along with the prime minister, flashing her wry smile and throwing back her thick and curly auburn hair. Unlike during her war years riding a bicycle in a Red Cross uniform around crumbled London, Kick, with her distinctive beauty in the Florida sun, now appeared more womanly than girlish, whether wearing pearls with a summer dress or all wet in her polka-dot swimsuit.
Eventually, Winston inquired about Kick’s father, with whom he had a tense encounter a few weeks earlier at Hialeah Park.
“He sends you best regards,” Kick answered.
Winston’s face soured. “He makes an exception in my case,” he said with a harrumph. The two men had a bitter falling out over the war, with Joe Kennedy opposing the war that ultimately claimed his oldest son, Joseph Jr.
The ambassador wasn’t pleased when his daughter, with some bemusement, repeated Winston’s comment to him. “Daddy took umbrage at this remark,” she noted in her diary.
Along with the inviting sun, Pamela Churchill sought refuge in Florida with the Kennedys for another reason besides getting a tan. As Kick knew, her friend had flown to America partly on the expectation of getting married to her wartime lover, CBS broadcaster Edward R. Murrow.
While in London together, Pamela fell deeply in love with the suave, older American journalist, who promised to divorce his wife when he returned home to New York. Murrow, who admired Winston Churchill, detested Joe Kennedy as an appeaser. He chastised Pamela for vacationing at his Florida home, which he likened to “staying with [Nazi Gestapo leader Hermann] Goering.”
In Palm Beach, however, Pamela heard from Murrow that he’d decided to remain with his wife and his newly born son, Charles Casey Murrow. casey wins, he telegraphed to Pam, who was shattered by the news. Her divorce from Randolph Churchill, filed in December 1945, had left her free to marry Murrow after their long affair. Even Randolph’s parents, former British Prime Minister Winston Churchill and his wife Clementine, seemed to wish for Pamela’s happiness away from their son. “Never forget not only are we devoted to you but you are the mother of my grandson,” Churchill told her.
While in Palm Beach, Pamela obtained a better sense of Joe Kennedy and his commanding grip on the lives of his children, now well into adulthood. Much of the talk touched on Jack’s impending congressional race in Massachusetts and how the family would rally behind him. Kick idolized her father and laughed off any suggestions about his questionable behavior. When a British tabloid portrayed the former U.S. ambassador as a playboy in Palm Beach, Kick couldn’t help sharing it with the rest of the family in one of their round-robin letters.
“I think it shows there’s a lot of life left in that old man of ours if he can start being a playboy at his ripe old age!” she teased. Whether Old Joe was attracted to Churchill’s former daughter-in-law later became a source of conjecture. Writer Truman Capote, a social friend with Pamela in the 1960s, suggested one of his novel’s characters was based on Pamela’s stay at Palm Beach, when the senior Kennedy allegedly slipped into her room in the middle of the night and pressed her into having sex with him. “The sheer ballsy gall of it—right there in his own house with the whole family sleeping all around us,” says the character Lady Ina Coolbirth in Capote’s book, repeating the story, never proven, he claimed Pamela recounted over lunch. For whatever reason, Pamela abruptly decided to leave Palm Beach. She stayed with another American friend, Betsey Whitney (the former wife of Jimmy Roosevelt who had married Jock Whitney) and then returned to New York, where Murrow attempted to renew their affair, without success.
Determined to return to Britain, Pamela contacted Lord Beaverbrook, seeking his advice as she had done since her marriage to Randolph. The press lord offered Pamela a job writing society articles for one of his London newspapers, and she traveled back on the Queen Mary. Like some real-life novella, Pamela Churchill’s arrival in England coincided with another twist in her love life: the return of Averell Harriman. In April 1946, President Truman appointed Harriman as U.S. ambassador to the Court of St. James, the same post once held by Joe Kennedy. Harriman replaced Gil Winant, whose bouts with depression had ended whatever effectiveness he once had in the job. Ave returned to London without his wife, Marie, or his daughter, Kathleen, and soon resumed his indiscreet affair with Pamela. The rumors started circulating again (with Randolph complaining to friends that he should have named Harriman as a co-respondent in his divorce proceedings), though Harriman’s tenure didn’t last long.
While having lunch with Winston Churchill in September, the White House called looking for him. The former prime minister guessed correctly that Truman wanted Harriman to fill the open job of U.S. commerce secretary, a Cabinet position in the postwar years far more advantageous than London. When Ave asked if he should accept the president’s offer, Winston didn’t hesitate. “Absolutely,” he replied. “The center of power is in Washington.”
The politically ambitious Harriman quickly accepted and jumped to Washington. Pamela remained in London while Marie Harriman continued living in New York. Ave’s wandering eye soon found another object for his affection, in the nation’s capital. He spent nights with Kay Halle, the heiress friend of both the Churchills and the Kennedys, with many Democratic Party connections of her own in town. Friends soon heard rumors that Harriman wanted to leave his wife for Halle. “On weeknights, the commerce secretary’s limousine was frequently parked at Halle’s house in Georgetown,” wrote Harriman biographer Rudy Abramson. “The proximity—and Halle’s high visibility and earnest intentions—made the matter more irritating to Marie than the wartime affair with Pamela had been.” But Halle never harbored a serious intention of marrying Harriman, her friend Timothy Dickinson told another biographer. “She knew if she married Averell she would be bullied beyond belief,” Dickinson explained.
Passion with the men in Pamela’s life was often mixed with sexual hypocrisy and double standards. Certainly Murrow’s withering criticism of her friendship with the Kennedys carried an odd stamp of moral disapproval. And at a chance meeting, Harriman “rather sanctimoniously blurted out that she was ruining her life” by flitting from one powerful man to another, implying that she was patterning her life on that of Lady Jane Digby, her ancestor often described as a courtesan. That stigma was unfair, insisted Pamela’s brother Edward. “While she was actually in a relationship, Pam was never unfaithful to her lovers,” Lord Digby said years later; “in most cases it was the man who strayed while Pam was entirely focused on that man.”
For Pamela, no friend seemed better able to understand these contradictions than Kick Kennedy, who returned to London soon after her Florida vacation. In their short existence, both young women had witnessed tragedy beyond their control, yet continued to define daily life on their own terms. “Mother and I were talking it over last night and decided nobody in the world twenty-five years of age has had the kind of life you’ve had or as interesting,” Joe wrote his daughter, suggesting her diary could become a best-selling book. Rather than spend her life in postwar America, though, Kick felt most comfortable in England, in the Brideshead Revisited world portrayed by her friend Evelyn Waugh. “I know it is unfair that so few should have so much etc. but there’s a certain grandeur, tradition, strength that is very much part of the England that would disappear without them,” she explained about the old homes and castles, especially the Devonshires’ Chatsworth estate. “I know my little brothers will think ‘Kick has gone more British’ than ever, my persecuted Irish ancestors would turn over in their graves to hear talk of England in this way but I don’t care. I think a landed aristocracy can be an instrument of good just as much of evil and when it is the former then —‘preserve it.’ (You’d better not let Grandpa Fitz see the above.)”
In this world, the Churchills were the defenders of a way of life that now existed mostly in words and memories—a paradox that the Kennedys (especially Kick), as Catholics bound by a sense of tradition, understood better than most. She teased and joked about many of the ironies, yet wished to remain a part of postwar England. In a letter home, she mentioned one of Randolph’s commando pals, Robin Campbell, who talked to her about his two years in a German prison camp, and spoke of the influence of religion on her friends. “Apparently Robin was so impressed by the Catholic Chaplain in the prison that he is thinking seriously of becoming one, much to the amazement and shock of his various relatives,” Kick wrote her parents. “Have heard the same thing about Randolph Churchill. Can you imagine him as a pillar of the Church?”
When Kick chatted with Lord Hugh Cecil, who had been best man at Winston Churchill’s 1908 wedding, she mentioned her own tragic marriage to the future Duke of Devonshire. In the eyes of her Catholic Church, Kick explained, “Billy and I had been living in sin.” Lord Cecil, a strong Anglican capable of outdebating Winston in their early days, merely rolled his eyes. “But so many of one’s friends are nowadays,” he sighed.
* * *
In postwar London, several of Randolph Churchill’s Oxford friends and commando veterans visited the white Georgian house on Smith Square owned by Kick Kennedy, the widowed Lady Hartington, a lively parlor for politics, the literary arts, and forgetting the heartbreaking past.
In Kick’s new home, located near St. John’s Church, where her friend Pamela Churchill had married Randolph years earlier, the two young women shared many laughs and gossipy stories about the Churchills and the Kennedys. “Kick’s house is really very cute, very nicely furnished,” described her sister Eunice during an October 1946 visit. “We hold a salon every night from 6 to 8 here at home; otherwise you can’t tell where we might be.” One constant visitor, Seymour Berry, the best man at Randolph’s wedding, dated Kick frequently enough that some friends thought they might get married. In this same circle of friends was Freddie Birkenhead (son of Winston’s best friend, the late F. E. Smith), who had served in Croatia with Randolph and Evelyn Waugh. By far, Waugh was the best known of Randolph’s friends to attend Kick’s dinner parties, and the most opinionated. While he found Kick attractive, Waugh thought the sentimental oil painting she kept on her wall of her dead husband, Billy (commissioned from an old photo of him in uniform) was “most God awful.”
As a Catholic convert, Waugh considered the Hartington wedding as unholy, a selfish act of apostasy. At one party, he sat next to Kick and gave her a lecture on Catholic marriage law. She seemed amused enough by this celebrated novelist not to take offense. Evelyn, who regained the roly-poly weight he’d lost during the war, mistook her attention for infatuation and noted, “The widow Hartington is in love with me, I think.” With Frank Waldrop, her old Washington newspaper editor, she later laughed about Waugh’s moralizing until she suddenly stopped. “You know, Frank, I had only five weeks with my husband,” she lamented, “and now he is gone.”
Inside her London group of acquaintances, William Henry Lawrence Peter Wentworth-Fitzwilliam, the Eighth Earl of Fitzwilliam (simply “Peter Fitzwilliam” to friends) emerged as the most intriguing and fateful for Kick. Her attraction to this swashbuckling, wealthy, and married war hero—far different in character from Billy Hartington—would lead to a secret love affair that once again caused conflict within the Kennedy family. Kick first met Fitzwilliam, the son of one of England’s richest families, at a June 1946 victory ball honoring the commandos. During the war, Randolph, Waugh, and Fitzwilliam, all drinking buddies from White’s, served together in the Middle East. Indeed, on the boat ride to Cairo, it was Fitzwilliam to whom Randolph lost a huge sum in a poker game—a financial crisis that ruptured Randolph’s marriage with Pamela and only added to Fitzwilliam’s notoriety as a gambler. In a begrudging tone, Waugh referred to Fitzwilliam as “king dandy and scum.”
In 1938, Kathleen Kennedy attended London event with mother Rose and sister Rosemary.
At the commandos ball, Kick turned plenty of heads with her pale pink gown, an effervescent smile, and a sense of humor that could captivate a room. That night at the Dorchester Hotel, Fitzwilliam’s wife, Olive, an heiress to the Guinness brewery fortune, served as president of the ball fund. Among the honored commando veterans, Fitzwilliam was singled out for a brave special mission during the war. Basking in the limelight, Peter nevertheless spent enough time with Kick to spark a romance, brazenly in front of his wife. By that point in their marriage, Olive had learned to look the other way when her husband flirted with other women. At such gatherings, she’d down drink after drink, enough so that she eventually became an alcoholic.
After the commandos ball, Fitzwilliam became a favored visitor at Kick’s home in Smith Square. Friends worried for her reputation with such a charming adulterer, and that she might wind up hurt. “You don’t know him—you don’t know him,” Kick insisted. Both lovers tried hard to keep their affair private, escaping London to the Fitzwilliam family’s estates throughout England and Ireland. A dashing man with thick dark hair, Peter showed enough business acumen with his outside investments to rival Joe Kennedy. His family, whose wealth was the stuff of legend, had the largest residence in England, a three-thousand-acre estate. This huge Georgian mansion, called Wentworth Woodhouse, contained 365 rooms (one for every day of the year), enough so that, in the eighteenth century, Peter’s ancestors gave guests paper wafers to leave in the hallways to retrace their way to its dining hall. Despite his many financial investments, Peter’s greatest interest centered on thoroughbred horse racing. He owned one of the best stud farms in England, and invited Kick to join him in racing excursions to France. Pamela Churchill came along with Kick as a sidekick and camouflage. “Kick was the perfect friend for Pamela, non-judgmental and fun-loving,” wrote biographer Sally Bedell Smith. “As the daughter of Lord Digby, Pamela knew her way around racecourses and fit in comfortably with turf society.”
In her letters home, Kick gave her parents glimpses of this glamorous world, mentioning a week-long trip to Paris with Pamela and Virginia Sykes, a former girlfriend of her late brother, Joe. In her correspondence, Kick could be catty and gossipy, the way all Kennedys enjoyed dishing in private. Aware of his mother’s disapproval of American Wallis Simpson and her affair forcing King Edward VIII’s abdication, Kick wrote of seeing the Duchess of Windsor and her husband on the social circuit and painted the woman he loved in pathetic tones. “Really, no one here takes any notice of them & the extraordinary thing is that I actually feel that she is jealous of what I, as an American, have got out of England and which has always been denied to her,” she told her parents. Kick played to the Kennedy family’s competitive streak in her Anglo-American exchanges. “After Pam’s dinner party, we went to her sister’s debutante party,” she wrote. “It gave me quite a turn to see all the ugly girls. Americans of that age certainly have them all beat.”
While visiting Ireland in November 1946, Kick’s more serious-minded younger sister Eunice stayed with her at Lismore Castle, the Irish estate owned by Billy’s family. They went to the races with a soft Irish rain falling, much different from the climate at the always sunny Florida track their father owned. “It was certainly the furthest possible cry from Hialeah,” Kick wrote to her parents. “But the characters around an Irish racecourse certainly make the whole day worthwhile.” The letter home mentioned Fitzwilliam, but did so misleadingly, avoiding any parental upset. Though Eunice accompanied her, Kick dared not explain to her sister the true nature of her relationship with the Eighth Earl of Fitzwilliam.
At Lismore Castle, Pamela Churchill joined Kick’s other high-powered friends from London when her brother Jack visited in September 1947. While on a European fact-finding mission with other House members, Congressman Kennedy tacked on his own extended holiday in Ireland with his sister. “I hope Jack will let me know when he is planning to arrive at Lismore and if anyone is coming from America,” Kick wrote home several weeks beforehand. “I don’t want everyone to arrive at once.”
Lismore, built centuries before, felt like a step back into history, a time when the British Empire dominated Irish Catholics in their own land. With some amusement, Kick reminded her family that she was now living in the place where Billy’s great-great-uncle was “brought in here, dying, when shot [sic] by Irish patriots in 1882.” With its ancient stone walls and turrets along the River Blackwater, the castle offered plenty of beauty and spacious rooms for Kick’s various guests. The list of invitees included Winston Churchill’s cousin Sir Shane Leslie, and most notably Anthony Eden, Churchill’s top foreign adviser, who had suffered the same family tragedy during the war as the Kennedys. In July 1945, Anthony lost his beloved fighter pilot son, Simon, in Burma. Yet Eden’s judgment of Churchill was far different from that of the embittered former ambassador Kennedy. “It is you who have led, uplifted and inspired us through the worst days,” Eden wrote Winston on V-E Day. “Without you this day could not have been.”
Despite their differences, Kick knew her father liked and respected Eden and would enjoy knowing of her invitation to meet Britain’s future prime minister. “Anthony Eden arrives today so by the end of the week he and Jack will have fixed up the state of the world,” she wrote home whimsically. Eden, a handsome man known for his distinctive clothing style, had already made an impression on Jack years earlier: Jack wrote to a friend that he’d been “sporting around in my morning coat, my ‘Anthony Eden’ black Homburg and white gardenia.” Talking politics at Lismore was part of the guests’ relaxation. “Anthony Eden, who was very easy to entertain, arrived loaded down with official looking Conservative documents but when he had been here only a few days got into the Irish spirit,” Kick reported. “Jack liked him enormously.”
Though nearly twice her age, Eden courted Lady Hartington with a fair degree of romantic interest. At a dinner party the year before, society hostess Lady Cunard had kept leaning toward them and asking loudly, “Anthony, don’t you think Kick is pretty?” followed in another breath by “Kick, don’t you think Anthony is wonderful?” Three months before his Lismore trip, Eden had escorted Kick to the Ascot Racecourse outside London, where he received a polite reception from the crowd. “They’ll cheer but the blighters won’t vote for us,” he whispered to Kick. The couple dined at Eden’s house, where Kick learned more about his troubled marriage. Eden’s wife, Beatrice, hated his political career, and she moved permanently to the United States after their son was killed in the war. “She [Mrs. Eden] is in America and refuses to return so he lives in a rather squalid little house with very few comforts,” Kick described. “He is a nice man and fascinating to talk to for me.” If Eden knew about Peter Fitzwilliam, it didn’t stop him from showing an interest in Kick even after the Lismore visit. “I long to see you,” Eden wrote in a lengthy missive to her. “I love your letters, especially when you write as you talk, for then I can imagine that you are here. How I wish that you were, and I do believe that you would enjoy it too.”
Strolling Lismore together, Kick let Jack know of her romance with Peter Fitzwilliam. She spoke glowingly of Peter, as if he were standing right before them, with an intensity Jack had never really known in his own love life. Jack listened fraternally, and didn’t prod or condemn. For now, Kick’s older brother was the only Kennedy family member she’d tell. Jack could be trusted to keep her secret.
While in Ireland, Congressman Kennedy remained intent on discovering his family’s roots. During his earlier 1945 trip, which included meeting Éamon de Valera, Kennedy had packed several books about Irish-American history. But on this trip, Jack planned an unannounced personal visit to the old Kennedy homestead in nearby County Wexford. While Kick’s other guests played golf, Jack convinced Pamela Churchill to accompany him for the four-hour journey in his sister’s American-made station wagon. Pamela shared the same sharp social antennae as Kick, but she wasn’t attracted to her successful brother. “In England we dated very much older men and Jack seemed, well, boyish,” Pamela recalled, though the congressman was three years her senior. “Skinny and scrawny, actually. Kathleen’s kid brother. Not eligible, so to speak.”
The road to Wexford was a long one. A century earlier in 1848, in the teeth of the Irish famine that claimed a million lives, Jack’s great-grandfather Patrick Kennedy left his family’s homestead (a drab whitewashed stone house with a thatched roof and only thirty acres on a tenant farm in small area known as Dunganstown) to begin a new lease on life in a poor immigrant section of East Boston. What happened to the succeeding generations of Kennedys would be nothing less than miraculous. They became emblematic of the rise of Irish Catholics, as America’s first large wave of immigrants who redefined their adopted nation. Rather than the British class lines of peerage or inherited wealth, Jack’s two grandfathers relied on their two faiths, Catholicism and the Democratic Party, to gain power in New England. Certainly Honey Fitz and P. J. Kennedy learned that hand shaking at parish Communion breakfasts, patronage deals through the political clubhouse, and the constant courting of ward bosses and Church hierarchy would pay off at the ballot box. Despite his millions from Wall Street and Hollywood, Joe Kennedy’s greatest triumph was his appointment to the Court of St. James, overcoming the strictures of his Irish-Catholic immigrant background. Nothing defined the differences between American and British society more starkly than this social ascendancy through Yankee ambition rather than noble blood and class distinctions. The Kennedys’ climb to the top proved “the hardest and longest move of all—inching up the rungs of the class ladder until the Kennedys stood near the top and could look as equals on the dukes and earls whose ancestors had ruled their native land,” JFK’s earliest biographer, James MacGregor Burns, explained. Joe Kennedy made sure his sons understood these lessons, prompting Jack’s curiosity to learn more about his family origins.
At the Kennedy farm in County Wexford, accompanied by Pamela, Jack discovered not much had changed since his great-grandfather left. “I’m John Kennedy from Massachusetts,” he said after his knock on the door was answered. “I believe we are related.” His distant cousin Mary Kennedy Ryan seemed dubious at first but eventually invited the two strangers in for tea.
The Kennedys who remained in Ireland had spent much of the past century trying to regain the land rights to their tenant farms from the British and supporting Ireland’s independence movement led by such politicians as de Valera. Mary Ryan herself had been a member of the old IRA’s women’s auxiliary during the 1920s conflict against the British, carrying guns and money, either in carts or under her dress, to a secret hiding spot near their farm. “Jack kept pressing on about his ancestors going to America and so on, trying to make the link,” recalled Pamela. As a treat, Jack took the Irish Kennedy cousins for a short ride in Kick’s shining new station wagon, accompanied by the former Mrs. Randolph Churchill. “They never could figure out who I was,” recalled Pamela. “‘Wife?’ they’d ask. I’d say no. And they’d say, ‘Ah, soon to be, no doubt!’”
After nearly two hours “surrounded by chickens and pigs,” Jack recalled, he “left in a flow of nostalgia and sentiment.” The trip reaffirmed the Irish stories he’d heard from his parents and grandparents. Neither Pamela nor Kick, however, seemed impressed. As their car pulled away from the Kennedy farm, Pamela turned to Jack with a remark meant as witty. “That was just like Tobacco Road!” she tittered, referring to the popular novel about rural life in Georgia. Jack wasn’t amused. “The English lady,” he later recounted, ”. . . had not understood at all the magic of the afternoon.” To Dave Powers and Ken O’Donnell, his Irish-Catholic political aides from Boston, he was much blunter: “I felt like kicking her out of the car.” At Lismore, Lady Hartington was even haughtier. After listening to her brother’s wondrous account of the Kennedy homestead, Kick mustered only a bemused question. “Well, did they have a bathroom?”
Throughout his Irish trip, Jack suffered an unexplained, debilitating illness with little relief. Eventually he flew back to London, staying at the Claridge’s hotel in Mayfair, where he collapsed. He sought help from Pamela, who had also returned to the city. “I need a doctor,” Jack told her desperately over the telephone. Pamela convinced her doctor, Sir Daniel Davies, also used by Lord Beaverbrook, to go see him immediately.
Kennedy’s wartime back injury and malaria usually provided a plausible public explanation for his often sickly appearance and yellowish skin tone. Pam’s doctor first diagnosed Jack’s symptoms as those of Addison’s disease, a chronic disorder of the adrenal glands with symptoms of weight loss, dizziness, nausea, diarrhea, and muscle fatigue. Sir Daniel kept him at the hospital, where Jack received lifesaving cortisone injections. “That American friend of yours, he hasn’t got a year to live,” the doctor informed Pamela.
Ravaged by his strange illness, Kennedy remained in a London hospital for weeks and was given the last rites of his church. In mid-October 1947, he traveled home with his mother across the Atlantic, confined to the sick ward of the Queen Elizabeth. He was then flown by charter plane from New York to Boston, and carried on a stretcher, drawn and pale, into the New England Baptist Hospital until he could recover. Misled by Joe Kennedy’s publicity men, the press claimed the congressman suffered from “a malarial attack.” No one suspected otherwise.
Friendship with the Kennedys required keeping secrets. As Kick’s confidante, Pamela Churchill became privy to Jack Kennedy’s biggest secret: the potentially fatal medical condition that could keep him from his family’s vaunting political goals. Yet there was no doubt she could be trusted, just as she was with so many intimacies about the Churchills. “I knew the Kennedys very well,” Pamela explained a half century later. “Kick was my closest friend in those days.” Pamela understood the power of such information. As the friendly siren of the Churchill Club during the war, she listened carefully to the conversations of American military brass, politicians, and prominent U.S. journalists—and then reported the most significant details to her father-in-law, the prime minister. “Basically, I’m a backroom girl,” Pam explained. “I’ve always said this and I’ve always believed it.”
In February 1948, Kick wanted Pamela Churchill to come with her again to Florida, just as she had when Winston visited in 1946. Visiting Palm Beach in winter gave Kick the chance to catch up with her family, to let them know more of her new life on the other side of the Atlantic. But this year the complicated love lives of these two young women didn’t allow for such an idyllic trip together in the sun. Kick had hoped Pamela’s presence might make it easier for her to tell her parents about her intention to marry Peter Fitzwilliam. Kick convinced Elizabeth Cavendish, her late husband Billy’s sister, to come with her to Palm Beach, as a false sign the Devonshires approved of Kick’s new love. In fact, Elizabeth harbored strong doubts and offered support only because Kick seemed “terrified” of confronting her mother. Among Kick’s London circle of friends, few believed Fitzwilliam would bring her anything but heartache. At dinner the night before she left for America, Kick burst out crying when David and Sissy Ormsby-Gore condemned Peter’s dishonorable character. Like the Jesuits she consulted, Kick heard the Ormsby-Gores predict ex-communication from the Catholic Church if she married Peter.
A sexual passion unlike she’d ever known before apparently compelled Lady Hartington to risk everything dear. “Her friends began to suspect that she had begun sleeping with him,” wrote her biographer Lynne McTaggart. “She didn’t seem to care anymore whether the affair was kept a secret or her reputation remained unsoiled.” Her old newspaper friend John White noticed a change in Kick’s demeanor; she was no longer the virginal Kennedy princess. Instead of duty, desire now motivated her actions; instead of obedient faith, a blinding happiness. “I was overjoyed to see that she had finally been awakened,” White observed. “Rarely in life do you see someone so bubbling over with love, everything that love should be, every bit of it. Poor old Billy Hartington. But again he probably would have been blown away if she had felt that way about him.” As word of her affair spread within her Smith Square salon, even Evelyn Waugh weighed in with advice. He’d later claim to Clarissa Churchill, Winston’s niece, that Kick sought his opinion about what to do about “le scandale Fitzwilliam.” Waugh suggested to Kick that having sex with a married man was relatively venial compared with the cardinal sin of leaving the Church. “If you want to commit adultery or fornication & can’t resist, do it,” Waugh cautioned, “but realize what you are doing, and don’t give the final insult of apostasy.”
During her nearly two-month-long stay in Florida, Kick never mentioned Peter’s name. Not until the last day of her trip, when the Kennedys were all together for a joyous occasion, did the twenty-eight-year-old Lady Hartington inform her parents like a wayward child. At the Greenbrier hotel in White Sulphur Springs, West Virginia—where Joe and Rose spent their 1914 honeymoon—the family gathered among some three hundred celebrities, wealthy tycoons, and society types to attend an April 17, 1948, gala hosted by the hotel’s owner. Hollywood star Bing Crosby sang “White Christmas” and other well-known tunes, while Kick convinced the band to play her favorite “How Are Things in Glocca Morra,” from Finian’s Rainbow, a new show on Broadway. Recovering from his illness, Jack flew in from Washington to join the fun.
Near night’s end, Kick stunned her mother by announcing her love for Fitzwilliam and their plans to marry when she returned to England. Kick’s adamant resolve was met by an even sharper, firmer rebuke from Rose. To this deeply religious matriarch, it seemed unconscionable that her daughter would break up an existing Fitzwilliam family to wed a divorced man. All Kick’s conciliatory letters from England—the vain effort to reconcile herself with her religion and her mother after marrying Billy Hartington, seeking her approval by attending religious retreats—now sounded hollow. As Rose realized, she’d been betrayed by both her daughter’s adulterous behavior and the apparent complicit knowledge of her son Jack and her own husband. No longer would Rose Kennedy look the other way. If Kathleen married this man, she emphatically told her daughter, she would no longer have anything to do with her, she’d be dead in her mother’s eyes. And if her husband went along with this unholy arrangement, Rose indicated there would be dire consequences for their own union. In a rare instance, Joe Kennedy kept silent. He knew Rose’s threat endangered their “family enterprise”—the magnificent Kennedy clan they had invested their whole lives in—and would shatter his relationship with his daughter Kathleen, who, Rose once told Lady Astor, was her husband’s “favorite of all the children.” Joe weighed his options as Kick left the next day for London.
In a sense, Joe Kennedy faced a similar predicament as Winston Churchill did with his favorite child, actress Sarah Churchill. She married two rakish husbands of whom the prime minister fundamentally disapproved. But whereas Winston did not seem able to keep his hurtful comments at bay, Joe proved far more adept and diplomatic with his children, even in the most inciting moments. He didn’t explode or risk the permanent expulsion of his daughter. “The measure of a man’s success in life is not the money he’s made—it’s the kind of family he has raised,” he insisted to a reporter in 1943, when his own political wilderness seemed to have no end. “In that, I’ve been mighty lucky.” At least for the moment, Joe honored his wife’s principled stand and did nothing to contradict her. Rather than fight, he soon left for Europe as part of a government commission study of the Marshall Plan. Kick contacted her father and pressed for a May 15 meeting in Paris. She felt strongly that if her father met Peter Fitzwilliam, he might recognize qualities similar to those in himself and give his tacit approval of, if not his blessing for, their marriage. To persuade her father, she planned to ask her British friend Janie Kenyon-Slaney and her husband, Max Aitken (Lord Beaverbrook’s aviator hero son), to join them in Paris. Max knew Peter; perhaps Beaverbrook’s son could ease the senior Kennedy’s objections. It was her father’s love, more than that of anyone on her family, that Kick didn’t want to lose.
Impulsively, a few days before this fateful meeting, the couple decided to fly from London to southern France, to spend a Whitsun holiday in Cannes drinking up the sun along the Riviera. Halfway into the journey, their chartered plane stopped in Paris because of stormy weather ahead. Peter impatiently called some horse owner friends, who agreed to share an impromptu leisurely lunch at a Paris café. When he and Kick returned to the airport, the plane’s pilot warned them that dangerous clouds remained in the skies, near the mountains leading to Cannes. Unaccustomed to not having his way, Fitzwilliam convinced the pilot to run the risk anyway, and he and Kick climbed back into the plane. Kick urged Pamela Churchill, who had come to the airport with them, to join them for the short trip. For reasons of her own, Pam declined. Instead, she “put them on the plane together,” as Pam recalled, and watched as they flew away.
Several hours later, Joe Kennedy received a call from the press at his Paris hotel suite letting him know that his daughter was dead. The small ten-person plane had lost control and crashed, killing everyone aboard. Kick’s battered body was carried by oxcart from the mountainside scene. The wartime widow’s search for happiness, the hope that her father might like Peter and support her decision to marry, was now over, covered up in misleading accounts of why they were together in the first place.
Alerted about the missing plane, Congressman Kennedy waited on a sofa in Washington, listening to Kick’s favorite song from Finian’s Rainbow, until the telephone rang again and he and his sister Eunice received the final word. Jack cried and eventually left the room to mourn alone. He later flew to Boston to gather with his mother, Rose, and siblings at the family’s Hyannis Port home. In his sorrow, Joe accepted a gracious offer by the Duke and Duchess of Devonshire allowing Kick to be buried near their Chatsworth castle, the scene of so many happier times before the war, rather than have her remains brought back to the States. Billy’s parents knew of Kick’s secret affair with Fitzwilliam and shared the Kennedys’ desire to keep it out of the obituaries. The ambassador had come to Paris with one of his favorite fixers, Boston’s former police commissioner Joseph F. Timilty—exactly the kind of gruff, bushy-eyebrowed accomplice Joe needed to tell a man he couldn’t marry his daughter. He’d even visited his Vatican friend Count Galeazzi, the pope’s top aide, for an ecclesiastical solution to Kick’s dilemma. Shattered by her death, Joe scribbled a note on his way to claim her body: “No one who ever met her didn’t feel that life was much better . . . We must not feel sorry for her but for ourselves.”
At Kick’s funeral, the former ambassador was the only Kennedy in attendance. Rose’s adamant condemnation of Kick’s behavior chilled the idea that the whole family might attend. At first Jack tried to go, but passport problems made him stay home. More than two hundred mourners paid their respects. Joe Kennedy, dressed in a rumpled suit, barely spoke. Many still viewed him as the appeaser who’d abandoned England at its most desperate hour. “He stood alone, unloved and despised,” recalled Alastair Forbes, one of Kick’s friends.
Despite their past antagonisms, Winston Churchill sent his written condolences on a wreath placed at Kick’s grave. Winston’s note seemed to acknowledge the loss of Kennedy’s oldest son in the war, the battlefield death of his son-in-law, and now the loss of his charming daughter the prime minister remembered so well. “Pray accept my sincere sympathy on your renewed grievous loss. Winston Churchill,” read the cable. The former ambassador thanked Churchill, acknowledging the way their families’ paths had crossed. “Rose and I are exceedingly grateful for your kind thoughts,” Joe wrote to Winston. “We know how greatly you admired Kathleen and that you will appreciate how we cherish the memory of her beautiful character.” Her funeral reflected how much of Kick’s life—flawed but always vividly intense—had been spent in England rather than America. Unlike her father, she’d been accepted by the British aristocracy as one of their own. Looking at her grave were several men who had loved her at separate times and in different ways: Seymour Berry, Tony Rosslyn, William Douglas-Home, Anthony Eden, and even Evelyn Waugh. Surrounding her coffin were other friends, such as Lady Nancy Astor and Brendan Bracken, and couples who had been part of her married life with Billy, including David and Sissy Ormsby-Gore, who had warned Kick about her involvement with Fitzwilliam.
Randolph Churchill represented his family as well as himself. Everyone knew of his divorce from Pamela, arguably Kick’s best friend at the time of her death, but Randolph had decided to come anyway. During the funeral services, he and Pamela spoke once again, not with rancor or any bitterness but with a tenderness they had not shared in years. Both seemed shaken by death’s sudden claim on Kick, the lively hostess of her Smith Square salon full of their friends, someone they’d known for most of their adult lives. The Kennedys had been a touchstone, part of their understanding of what it meant to be American. As his father’s representative, Randolph first met Kick upon the Kennedys’ 1938 arrival in London, before any other Englishman or Pamela had heard her name as a debutante. Now, a decade later, Lady Hartington, known as Kick, the embodiment of this special Anglo-American relationship, was gone. The twisted wreckage had left both Pamela and Randolph searching for answers.
Pamela Churchill embraces husband Randolph during World War II as Winston looked on.
To her divorced husband, Pamela admitted her life had been tougher than she expected after leaving the Churchill family’s protective bubble. Floundering in his own way, Randolph recognized how much both his parents still adored Pamela with their young son, Winston, and that perhaps his own rudderless life might be given new direction if they got back together as a family. Following Kick’s burial, Randolph proposed a reconciliation with Pamela. He arranged for a weekend getaway at the castle-like home of a friend, with champagne on the ready. Like a newlywed, Randolph hoped for a second honeymoon with Pamela, and used all his oratorical skills to plead his case. They talked about their mutual employer, newspaper baron Lord Beaverbrook, and how Winston’s wealthy ally had come to control so much of their lives, just as Randolph once feared. The war had ruined so many marriages, but Randolph argued that theirs could be salvaged, if only she believed in him.
As they drove a sedan into the countryside, however, Randolph got lost, and Pamela slowly came to her senses. She realized he was no longer the charismatic Adonis figure of his youth, but a lonely, bloated thirty-seven-year-old man with receding gray hair and an uncertain future, who seemed not to have learned any lessons from the past. For all his kindnesses, Randolph could easily revert to being a self-centered lout, looking for a maid rather than a wife. No matter how vulnerable she might feel, Pamela concluded that she was better off without him.
Memories of Kick remained buried with her at Chatsworth. With no more familial ties in London, Joe and Rose Kennedy focused their attention almost exclusively on Jack’s career in America and the admirable lives of their other children—such as Robert, for whom England was a more distant memory. “He [Bobby] is just starting off and has the difficulty of trying to follow two brilliant brothers, Joe and Jack,” the senior Kennedy wrote to Beaverbrook in 1948, thanking him for an encouraging note sent to his third son. “That in itself is quite a handicap, and he is making a good battle of it.”
Jack’s memories of Kick and Joe Jr. in England taught him to embrace the immediacy of life, rather than any doctor’s prediction of imminent death. No one had believed in Jack more than his favorite sister, Kick. He had trouble sleeping at night, dreaming about her. “If something happens to you or somebody in your family who is miserable anyway, whose health is bad, or who has a chronic disease or something, that’s one thing,” Jack explained years later to James MacGregor Burns. “But, for someone who is living at their peak, then to get cut off—that’s the shock.”
Jack returned to London that summer but found it too wrenching to visit Kick’s grave at Chatsworth, which bore the epitaph “Joy She Gave, Joy She Has Found” etched on her tombstone. It fell to Jack to help settle Kick’s estate. He sorted through various entanglements of his sister’s life even more complicated than his own. After meeting with Kick’s housekeeper, learning more details of his sister’s love affair with Fitzwilliam, he instructed, “We will not mention her again.”
In years to come, the loss of Kathleen remained too painful for Joe and Rose Kennedy to discuss among themselves or with others, including their children. Rose turned again to her Church for solace and, ironically, relied on her newfound friendship with the Devonshires, the Protestants she once dreaded as in-laws, to settle the remaining loose ends of Kick’s life. “We have received most of the things in America, except two pictures given to her by Pamela Churchill,” Rose told a lawyer disposing of Kick’s belongings in London. “I believe the Duchess of Devonshire is holding them for me.” Without the deep faith his wife sustained, Joe never felt more despondent. The grand dreams built around his most stellar children no longer existed. “The sudden death of young Joe and Kathleen within a period of three years has left a mark on me that I find very difficult to erase,” Joe explained to Beaverbrook. “What a horrible mess the world is in. I am afraid I see very little hope on the horizon.”
At Christmas that year, when Pamela Churchill contacted him, Joe Kennedy was still morose. Yet he tried acting cheery for his daughter’s friend, giving out his overfamiliar brand of fatherly advice. “I am afraid that Palm Beach is never going to be the same without Kick,” he confided. “Of course, I hear about you every now and then, but usually that some rich fellow is passionately in love with you. I don’t blame them, but it is about time you gave some of these Americans a chance. Unless you hurry, there won’t be any rich ones left.”