Friends in High Places: When the Churchills met the Kennedys

Winston Churchill’s childhood, at least the first “wavering lights and shadows of dawning consciousness,” as he put it, began in the most unlikely of places: Éire. “My earliest memories are Ireland,” he explained in his autobiography. “I can recall scenes and events in Ireland quite well, and sometimes dimly, even people.” The Churchills wound up there when Winston’s father, Lord Randolph Churchill, gained an appointment to serve in Ireland during the late 1870s. It was a predominantly Catholic land then, yearning for its independence from Protestant Great Britain.

In Ireland, young Winston quickly learned that not all imperial inhabitants appreciated British rule. The stabbing of Lord Frederick Cavendish, the chief secretary for Ireland, by four knife-wielding Irish extremists who butchered Cavendish in Dublin’s Phoenix Park, became part of Churchill lore. (A visiting former Boston mayor, John F. Fitzgerald, known as Honey Fitz, on a trip with his young daughter Rose in 1908, called the murder spot “a Catholic monument.”) Lord Randolph Churchill told reporters that he felt “confident it was the work of Fenians,” the notorious Irish rebels.

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The adult most responsible for Winston’s parenting, his beloved nurse, Mrs. Elizabeth Everett, detested these Irish-Catholic upstarts and their religion. “Mrs. Everett was very much against the Pope,” Winston recalled. “If the truth were known, she said, he was behind the Fenians.” Naturally, Mrs. Everett’s view “prejudiced me strongly against that personage and all religious practices supposed to be associated with him.”

Throughout his adult life, Churchill respected the Protestant customs and creed of the Church of England, though he was not particularly religious. Nor did his prejudice towards Catholics seem overt as a public official—except, of course, to Irish Catholics in the 1920s, who blamed him for the brutality of the British Black and Tans armed force trying to stop their war for independence.

In private, some of Winston’s view of Catholicism came into play when his only son, Randolph, decided to marry Pamela Digby shortly after meeting her in 1939. Concerned with carrying on his family’s legacy, Winston favored this rather rushed union, quickly put together before Randolph went off to World War II. But Winston did have one reservation, which he posed to Pamela in private the first time they met at Chartwell Manor, the British leader’s home. Pamela remembered seeing Winston come out of his studio, a short distance from the main house, and walk up the grassy hill toward Randolph and his intended bride.

“Your family, the Digby family, were Catholic but I imagine you are not still a Catholic?” he said, looking at her very severely. “Are you Catholic?”

“No, I’m not,” Pamela replied.

The agnostic in Winston, unaffiliated with any church or particular deity, surely did not mind. But the historian in Winston seemed vaguely to remember that the Digbys were Romanists. As a royal monarchist looking for a rightful heir, this possible variance from the Church of England was something he needed to know. He did not want to see religion become an issue. Jack Churchill, Winston’s stockbroker brother, had married a Catholic, and their children were being reared in the Church of Rome. Winston’s inquiry about her religion seemed to carry a slight distasteful implication: that he was part of “the majority of that type of English person who is anti-Catholic,” Pamela later explained.

Pamela assured Winston that he need not worry. She had been baptized at infancy in the Church of England. While their papist affiliation was true centuries before, the Digbys had been Protestants in good standing for years among the peerage, and faithful Conservative Party members, too.

“Yes, you had your heads chopped off in the Gunpowder Plot,” Winston now recalled.

“That is right—Sir Everard Digby,” Pamela replied. (Actually, Sir Everard, converted to Catholicism by a Jesuit, was hanged, drawn and quartered at the Tower of London for his involvement in an attempt in 1605 to blow up the House of Lords and kill King James I.)

Winston appeared relieved. “That being out of the way—that I was not a Catholic—he became very much on our side,” Pamela recalled. “But the rest—Clemmie and my family—were very practical and didn’t think it was a good idea.”

Love in haste prevailed. The Churchills presented Randolph’s proposal as grandly as possible. “Since the age of 19, Randolph Churchill has had a varied and sometimes spectacular career in politics and newspaper work,” The New York Times reported about the nuptials. On the way to the altar, it was learned the Digby home at Minterne, Dorset, had once belonged to Gen. Charles Churchill, a brother of the great Duke of Marlborough. Wedding chroniclers noted that the two families shared this fateful association with Winston’s hero, the subject of his massive biography, as if they were joined by fate rather than mere coincidence.

On Oct. 4 newsmen and a large crowd assembled outside St. John’s Church, craning their necks for the real star of the show, Winston Churchill, who showed up in a black felt hat instead of his naval cap. Many friends and relatives cheered the newlyweds on, including the toast-making lord Freddie Birkenhead and Vic Oliver, Churchill’s comedian son-in-law. Randolph appeared gallant in his Hussars uniform, while the voluptuous Pamela, no longer frumpy, wore a blue dress and a convincing smile. As they left the church, the couple marched under the raised swords of Randolph’s fellow Fourth Hussars, a splendid exit for a man presumably going soon into battle.

Joe Kennedy Steps In

The day’s majesty and exchange of eternal vows did not sweep away all doubts about this union, however. After their wedding, Randolph confessed to Pamela that he had nearly married another woman because of the confusion surrounding their three-week courtship. When Pamela seemed to waver in her acceptance, Randolph had decided to keep searching for a bride to sire his heir.

On Sept. 19 he finally found another woman agreeable to marriage and “would have done so but for the refusal of the Archbishop of Canterbury to grant a special license for that day.” Looking for an advocate to convince the Anglican head of the Church of England, Randolph enlisted the most unlikely of arm twisters: Joseph P. Kennedy, the Irish Catholic from Boston.

Documents show young Churchill privately approached the American ambassador for this extraordinary favor—most likely to Joe’s Machiavellian delight. As with Jimmy Roosevelt, the eldest son of President Franklin D. Roosevelt, Joe had tried to cultivate a friendship with Randolph as a subtle way of influencing sons and compromising their fathers. “In middle age he began to take on younger protégés,” his granddaughter Amanda Smith later described in her own fashion. “Often these were the children of extraordinary famous and very busy parents.”

Joe Kennedy carried his own sensitivities as a member of a religious minority in the United States, then also a primarily Protestant nation. Kennedy believed the patrician president, who had sent him to London as U.S. ambassador in 1938, nevertheless harbored bigotry toward Irish Catholics like him. “I got the impression that deep down in his heart Roosevelt had a decidedly anti-Catholic feeling,” Joe eventually wrote in his diary. “And what seems more significant is the fact that up to this time he has not appointed a prominent Catholic to any important post since a year ago last November.” Kennedy concluded that “this [anti-Catholic] feeling [was] firmly imbeded [sic] in the Roosevelt family.”

Contrary to most historical accounts, Randolph Churchill “rather liked” Joe Kennedy originally, Pamela later recalled. Randolph attended many social events with the Kennedys in London and undoubtedly knew of Joe’s friendship with the American Bernard Baruch and the British press magnate Lord Beaverbrook, both wealthy men close to his own father. Furthermore, Randolph’s job as a political writer for a London daily made the headline-grabbing ambassador fascinating, even if Randolph was gradually repulsed by his views. “In fact, at one moment, Randolph saw quite a lot of Kennedy,” Pamela later explained. “I guess he didn’t really like him, but he was a good source. He was working for a newspaper.”

To his wife, Rose Kennedy, the ambassador explained that 28-year-old Randolph had sought advice about marrying an actress and that he’d been turned down—only to wed Pamela Digby instead a week later. “Nuts! I call it,” Joe concluded in a Sept. 26, 1939, letter home, sparing his Catholic wife any details about the Archbishop of Canterbury.

The decision to seek Joe’s help underscores Randolph’s personal desperation as well as his ill-informed judgment. Joe didn’t consider himself particularly friendly with the archbishop. Rather, Joe was a friend of the new king, George VI, who had confided that the archbishop and Winston Churchill had cruelly drawn attention to “the defect in his speech” during the abdication crisis, according to Joe’s diary. Over brandy one night, the king told Joe he felt vindicated after finishing a successful speech at Guildhall in front of them. “I made that speech straight at Churchill,” the king told him. (This version differs substantially from the relationship portrayed in the 2010 movie “The King’s Speech,” in which Churchill encourages the stuttering king.)

If Randolph Is Not Killed

Thus, with no particular patron on his side, Joe could not likely have convinced the archbishop to change his mind about a special allowance for Randolph. Years later, Pamela said, she eventually learned about Randolph’s frantic request to Kennedy. “My husband has asked him, the American Ambassador, to use his utmost endeavours with the Archbishop of Canterbury to obtain such a special license,” she recounted in annulment records.

Before her own vows, Pamela also harbored doubts about this marriage. She had hedged her bets on success with Randolph in a way that appalled more than one friend and family intimate. Her father’s good friend Lord Margesson, the Conservative Party’s chief whip, a man known for getting his way in Parliament, “took me for a long walk in the country and did his utmost to dissuade me,” she recalled. Another friend, a woman who had known Randolph her whole life, tried to persuade Pamela beforehand to reconsider. “He has tried to marry every girl in London for the last two years,” she implored.

No longer a debutante, Pamela gave the most practical of replies. Her answer would set the stage for the Churchills’ family life for the next several years. “Well, if he [Randolph] is not killed & we do not get on well together,” she declared, “I shall obtain a divorce.”

As much as he initially liked the Kennedys, however, Randolph realized the new ambassador’s Irish-Catholic background might pose a problem. When Honey Fitz, the ambassador’s 75-year-old father-in-law, showed up in London for a short visit that spring, Randolph told Londoners that the former Boston mayor was known for “his excellent singing voice [and] was the first American politician to discover that the best way to poll the Irish vote was by twisting the tail of the British Lion.”

In his unpublished memoir, Joe Kennedy acknowledged that the large public attention surrounding him “was heightened by the fact that my Irish-American background and my family of nine children were not in the normal tradition of our earlier envoys to the Court of St. James.” His selection was a barrier breaker, a milestone for his Irish Catholic heritage. Both Joe and Rose recognized the immeasurable long-term benefits for their family’s future in politics. Besides, Roosevelt’s selection of him (regardless of his private views of the church in Rome) was a giant step forward for Irish Catholics, the kind denied for decades in the United States.

“You don’t understand the Irish,” explained Thomas Corcoran to another F.D.R. aide, Harold Ickes, who wondered why Kennedy politically coveted this appointment abroad. “London has always been a closed door to them. As ambassador of the United States, Kennedy will have all the doors open to him.”

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