How JFK’s Lifelong Friend Helped Shape U.S. Foreign Policy

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Twenty-one months into his term in the White House, the youngest elected president in American history found himself facing a crisis so grave that it threatened not only his political life but also humanity itself.

John Fitzgerald Kennedy was sitting in the dining room of the “Suite of Presidents” in Chicago’s historic Blackstone Hotel, eating a bowl of the hotel’s famous Boston clam chowder while he scanned the local newspapers. It was Saturday, October 20, 1962, what would later be known as Day 5 of the Cuban Missile Crisis. The night before, he had headlined a fund-raiser for the Cook County Democratic Party. Now he would fly off for a day of vigorous campaigning for Democratic candidates in the upcoming midterm elections. As Kennedy began reviewing the day’s schedule—which would take him to five states, starting in Milwaukee and ending in Seattle—a phone call came in from his brother Bobby, the attorney general. He had ominous news. After four intensive days of deliberations, the Executive Committee of the National Security Council (ExComm) had agreed on two options for the president to take in response to the discovery days earlier of Soviet ballistic missiles in Cuba. The first was to launch an air strike, the second to impose a naval “quarantine”—a ring of ships around Cuba to keep Soviet ships from delivering more missiles—with the threat of future military action. Either one could result in a nuclear confrontation with America’s most formidable enemy.

Kennedy instantly scrapped the day’s campaigning and prepared to return to Washington to meet with the ExComm. But since the public still knew nothing about the existential threat just 90 miles from Florida, the president needed an excuse for heading home early. So he turned to the oldest trick in the schoolkid playbook: fake an illness. As Kennedy boarded Air Force One, the country was told that his doctor had found him running a low-grade fever and ordered him to return home forthwith. The patient obliged, even donning a borrowed gray fedora hat for only the second time in his presidency to demonstrate he was taking all necessary precautions.

Once back in Washington, Kennedy made four decisions. First, he called and asked his wife, Jackie, to come back from their weekend getaway in Virginia. He wanted her and their two children, Caroline and John Jr., within the safe confines of the White House. The president then scheduled a national television broadcast for Monday night, when he would reveal the crisis at hand and explain how he intended to address it. Third, after a heated debate with his ExComm, Kennedy opted for the less aggressive strategy of a blockade to keep Soviet ships from delivering their missiles. And finally, early on that Sunday morning, he called one of his closest friends and asked him to “come unseen” to the White House shortly before lunch. For nearly a quarter-century, the president had been having an ongoing conversation with this friend about leadership and decision-making in the midst of crisis. But this time the discussion no longer dealt with hypotheticals. If ever Kennedy felt a need for the wisdom, counsel, probity and friendship of David Ormsby-Gore, it was now.

A few hours later, Ormsby-Gore was ushered into the Yellow Oval Room in the second-floor residence. There he met the president, who was grappling with how to manage a complicated military operation and then explain it to the nation in a televised address the following evening. The two men recognized the stakes would never be higher: Just one false step could set off a nuclear war. That night over dinner and afterward, they labored over the words Kennedy would use in his address to the nation. Then, over the six days and nights following the address, Kennedy and Ormsby-Gore would draw deeply on a 25-year conversation that had continued throughout their friendship to help guide the young leader through the worst crisis of his presidency. Deliberating in the Cabinet Room, taking meals in the residence, and talking late into the night, they finally had an opportunity to demonstrate what true leadership should be in the crucible of conflict.

That Kennedy would choose Ormsby-Gore as one of his key confidants is testament to the fullness of a bond forged at the outset of World War II and deepened over the ensuing two decades. More remarkable still is the fact that the man the president entrusted with such sensitive information during the Cuban Missile Crisis was neither a member of his government nor even a citizen of the country he led. He was the British ambassador to the United States, a lord-in-waiting, a cousin by marriage to a sibling and a man of exquisite social grace and fierce intellectual firepower. (Kennedy often told friends that next to national security adviser McGeorge Bundy, Ormsby-Gore was the most brilliant man he had ever met.) Naturally, then, Kennedy often called him for support during trying times and for company during more relaxed moments.

As British prime minister Harold Macmillan later put it, “You see, the President had three lives; he had a smart life, dancing with people not in the political world at all, smart people, till four in the morning; then he had his highbrow life, which meant going to some great pundit…and discussing his philosophy; and then he had his political life. And David belonged to all three.” Ormsby-Gore wore that distinction with modesty, never seeking to leverage his relationship for personal fame or professional aggrandizement. Secure in himself as well as in his duty to his country and to Kennedy, his only goal as confidant was to advance ideas and policies he thought best served the interests of his friend, his native country, and the “special relationship” between Britain and the United States.

Bundy later reflected that no one could overestimate “how intimately and how completely” the two friends discussed matters. Ormsby-Gore, Bundy continued, “was probably in the [White] House more than any other person with a serious concern for affairs” during Kennedy’s presidency. And no couple spent more time on weekends with the First Couple—in Hyannis Port, Palm Beach, Glen Ora, or at the White House—than David and Sissie Gore, a tribute to their intellectual and social verve. Barbara Leaming, who in The Education of a Statesman first unearthed Ormsby Gore’s critical role in Kennedy’s life, perhaps summarized it best: “The friendship would prove among the most important of Jack’s life and have immense historical ramifications” during his dramatic years in the White House. In particular, the friendship between the two men would change the trajectory of the Cold War.

John Fitzgerald Kennedy never wanted for friendship. Witty, urbane, and handsome, a man from a prominent family and with a hunger for intellectual stimulation, Kennedy made friends easily and, with few exceptions, kept them. His life was short, only 46 years, but his list of friends ran long—so long that as president he felt no need to add to it. “The presidency is not a good place to make new friends. I’m going to keep my old friends,” he quipped.

As a child and adolescent, Kennedy bonded most easily with his sister, Kathleen, known to all as “Kick,” though the sibling he would ultimately be closest to was his younger brother Bobby. It was Kick who would introduce Jack Kennedy and Ormsby-Gore.

Kick’s entry into polite British society in the early spring of 1938 was proving far more difficult than she had ever anticipated. The daughter of America’s brash new ambassador to the UK, she arrived shortly after her 18th birthday with the intention of staying at least until the fall. During that time, she would follow the rituals of well-heeled English daughters by being presented at court and having her own debutante party. But two things weren’t working, leaving Kick sorely frustrated: The most sought-after boys weren’t laughing at her jokes, and she wasn’t thrilled by the few girlfriends she had managed to make.

All that changed one magical weekend in April that year when Kick attended her first weekend party at a proper English country house and met young David Ormsby-Gore, an Oxford University student a month away from turning 20. He too stood at a crossroads of sorts. David was the second son of Billy Ormsby-Gore, the seventh-generation Gore to sit in the House of Lords as Lord Harlech, baron and owner of the family’s extensive landholdings in Wales and Shropshire. At various points in David’s youth, his father would play prominent roles in Britain’s foreign affairs, including serving as a member of the British delegation to the Paris Peace Conference in 1919. In 1933, as Britain’s delegate to the League of Nations and an unabashed supporter of Zionism, his father made international headlines when he bucked official British policy by denouncing Hitler’s racial theories and attacking Mein Kampf. David’s mother, meanwhile, was the granddaughter of Lord Salisbury, a prime minister under Queen Victoria.

As part of the London aristocracy, David followed the traditional path of attending Eton, where he became known more for his pranks and wit than for his academic mastery. One day a fellow student committed suicide, and, as the story goes, the housemaster called an assembly and asked the boys if anyone knew why. Ormsby-Gore raised his hand and asked, “Could it have been the food, sir?” During the year before his last at Eton, David’s older brother Gerard died in an automobile accident. Under the rules of primogeniture, David as the second son would now inherit the Harlech barony and the new title of “lord-in-waiting.” Instead of settling into the modest and private life he longed for, family tradition dictated that Ormsby-Gore enter the House of Commons prior to assuming the title—a public life he neither wanted nor felt suited him.

When David met Kick that spring evening, whatever unease each may have felt vanished almost instantly. By the end of the weekend, Kick had found the squad that would sustain her in Britain for the following decade. With her older brother Jack due to arrive in London any day, Kick couldn’t wait to show them off. And by the time he left three months later, Jack, like Kick, would have his own London social circle, with David Ormsby-Gore at its center.

Precisely how, when, and where Kennedy first met Ormsby-Gore remains lost to history. Several accounts suggest they linked at a dinner party at the ambassador’s residence or at the Epsom horse races. The novelist Evelyn Waugh had a different recollection, saying they met “over supine bodies in a squalid basement bottle-party.” What is certain is that once Kick sparked their connection during the early summer of 1938, Jack’s attraction to Ormsby-Gore and his fellow Brits would prove as strong for him as it had been for her.

Jack by this time felt almost magnetically drawn to London. Even before he met Ormsby-Gore and his elite friends, he already knew a great deal about their family lore, including the stately homes they owned, the major scandals they endured and even their quirky legacies. His studies at Harvard over the past two years had been entirely consumed with English and European history (he claimed to be reading up to 12 books on the subject weekly), and now his father was the U.S. ambassador to England. Kennedy had spent the previous summer traveling across Europe, trying to better understand the prospect of war facing the continent. Earlier, he had studied briefly at the London School of Economics after graduating from Choate. Settling down in London now for another summer, Kennedy planned to focus his time understanding what Hitler’s threatening agenda might portend for the rest of the world.

For his part, while at New College, Oxford, Ormsby-Gore closely followed the current political scene and could parse complex public issues with anyone. Later on that summer with his new friend in tow, he would attend House of Commons debates, fascinated by the discourse over how and when Britain should confront Hitler’s rising menace. Still, Ormsby-Gore believed he lacked that singular drive—that killer instinct—to be a politician himself, a sobering thought for a man expected someday to succeed his father and sit in the House of Lords. At a time when his friends were starting to get more serious about their futures, he felt directionless, more consumed by his obsession for fast cars than thoughts of how he would make it in the world.

As Kennedy and Ormsby-Gore discovered during that summer of 1938, they had much in common. Both were second sons and viewed by their fathers as the lesser. Both were highly educated—each studying at prestigious universities—yet not quite sure how to apply their book knowledge to the real world. Their conversations were “swift and sharp,” just as both liked them. And increasingly that summer, those discussions grew more and more substantive.

One question in particular riveted the two men: What does it mean to be a true leader in a democratic society? It was an issue they would return to time and time again over the next 25 years, culminating with the future of the world at stake.

This critical question of how leadership should be wielded intensified that summer with the publication of Winston Churchill’s book Arms and the Covenant, a collection of his speeches since 1932 advocating for rearmament in the face of German militarization. Churchill’s polemics forced Brits like Ormsby-Gore to confront the question of whether the previous six years—a period when Germany seized territory, proclaimed its master-race superiority, and strengthened its military while England stood still—had been squandered. Churchill called them the lost “locust years,” a stinging indictment of Stanley Baldwin, Neville Chamberlain’s predecessor as prime minister. In Churchill’s depiction, a weak Baldwin refused to address the growing threat of German militarization because he capitulated to a British electorate adamantly opposed to intervention. Baldwin later defended his inaction by arguing that had his government betrayed public sentiment and rearmed, the pacifist Labour Party would have swept into power—leaving the country even weaker.

This schism between Churchill and Baldwin “posed large questions for the young men about the role of leadership in a democracy,” as historian Fredrik Logevall writes. “Should a leader pursue a course of action, that, however meritorious on strategic or ethical grounds, might cause his political downfall? How much should public opinion matter in policymaking? Should a leader take care not to get too far ahead of the electorate, as Baldwin seemed to argue, or was Churchill right to insist that he must speak his mind, must educate the public, whatever the consequences to his own standing?”

Ormsby-Gore and his British friends firmly sided with the Churchill camp, convinced that a true leader must take action to preserve and protect the greater good of the nation, regardless of the whims of the public. Chamberlain’s submission at Munich later that fall and Hitler’s subsequent violation of the pact reached there only cemented their opinion. Kennedy, however, refused to take a firm position that summer, in part because his father’s increasingly pacifist views put him in conflict with Churchill. And for much of the next 20 years, Kennedy’s actions on this question would remain nuanced. He criticized Britain’s appeasement of Germany in his senior thesis, Why England Slept, but refused to place the blame on either Baldwin or Chamberlain, instead faulting the entire British political system for failing to meet its responsibilities. Sixteen years later, in his Pulitzer Prize-winning Profiles in Courage, he celebrated eight US senators who had demonstrated Churchillian leadership, risking their political careers to pursue causes they thought just. Still, even as he aspired to govern guided by Churchill’s ethos, Kennedy often struggled to apply it in his public life, veering, as Leaming writes, “between Baldwin and Churchill, between politician and statesman.” Only when he reached the presidency, and came face to face with the greatest existential threat the world had ever faced, would he finally and fully resolve this question—with Ormsby-Gore at his side.

Jack returned to Harvard that fall while Kick remained in London. David, a Protestant, fell in love with Sissie Lloyd Thomas. Further cementing Ormsby-Gore’s connections to the Kennedy family, Sissie had become Kick’s best friend in London, and she would remain so for the rest of her life.

Once the war began, Joe Kennedy wasted no time moving his family back to New York and an ocean away from Hitler’s menace. The ambassador however remained at his Embassy post on Grosvenor Square.

The war years kept Ormsby-Gore and John Kennedy apart, each occupied with serving his country and, in the case of David, marrying Sissie and raising a family that now counted two young children. While Ormsby-Gore avoided any live combat in the Territorial Army, Kennedy became a war hero, saving his PT-109 crew from near-certain death after a Japanese cruiser sliced his boat in half. If the circumstances of the ramming left some wondering whether it could have been avoided, no one doubted Kennedy’s heroism afterward. Of his 12 crewmates, 10 survived, many because of Kennedy’s will and physical exploits over five excruciating days while they awaited rescue. For his heroism, Kennedy would receive the Navy’s highest award for gallantry, the Navy and Marine Corps Medal. He also received a Purple Heart.

Over the next half-decade, the two men would begin their ascents in the political world. Kennedy was the first and the more ambitious, quickly leaving journalism to run for a House seat in the Boston area in 1946 and winning the primary and general election easily.

In 1950, Ormsby-Gore won a seat in the House of Commons—almost by accident. Filled with ambivalence, Ormsby-Gore took the baby step that summer of putting his name on a list of Conservative candidates for the seat. He never expected to be chosen, but the committee selected him thanks to his social status and his experience overseeing the family estate. Later, the voters elected him to Parliament.

A few months after Ormsby-Gore’s surprising ascendance, Kennedy arrived in London to see his old friend newly absorbed in his own role as a public official. For this trip, in addition to the usual briefing papers on British defense policy, Kennedy brought with him a brown-paper parcel filled with food, nylon stockings and other wares he dispensed to Ormsby-Gore and friends suffering from shortages caused by an English economy in free fall. In addition to the usual rounds of dinners, golf and afternoons at “drafty country houses,” they spent the bulk of their time talking about foreign policy, seeking to shape themes they had pondered together in their youth into cogent worldviews. Both by then were staunch anticommunists and believed that only a unified Europe, with a strong U.S.-UK alliance, could act as an effective bulwark against an expansionist Soviet Union. They would put their shared convictions and strategies into practice many times over the next dozen years.

As the 1950s advanced, so too did the public careers and private lives of the two friends. In 1952, 35-year-old Kennedy was elected to the Senate, narrowly defeating the incumbent Henry Cabot Lodge. Meanwhile, Ormsby-Gore swiftly rose up the hierarchy of the Commons and the British Foreign Service, due in no small measure to the mentor he found in Selwyn Lloyd. When Churchill was reelected prime minister in 1951, he appointed Lloyd minister of state for foreign affairs, the effective deputy to the foreign secretary. Lloyd needed a parliamentary private secretary and offered the position to Ormsby-Gore; accepting it changed Ormsby-Gore’s life. At the UN General Assembly session that fall in Paris, where the topics included Soviet-bloc containment and disarmament, Ormsby-Gore quickly established his expertise in both realms, putting him on a path that would have profound benefits for both his own career and that of his friend in the U.S. Senate.

A year after becoming a senator, Kennedy became a husband, marrying Jacqueline Lee Bouvier before eight hundred family members and friends at St. Mary’s Roman Catholic Church in Newport, Rhode Island. No fewer than five priests took part in celebrating the wedding mass.

With a larger prize than a Senate seat in his sights, Kennedy now turned his attention to the issues that would give him added credibility and position him as a future presidential candidate. Once again, he confronted the question of what constitutes leadership in a democracy, this time in the context of the Cold War. In an essay for the New York Times Magazine published a year after his wedding, Kennedy argued that weapons of mass destruction now in the possession of the two world superpowers made the decisions of its leaders more consequential than ever before. Sixteen years after first debating with Ormsby-Gore about the disparate approaches of Baldwin and Churchill, Kennedy at least for the moment had moved decisively toward the Churchill camp—a shift made abundantly clear in the way he advocated for strong, unwavering diplomacy as a response to the Soviets, rather than the overly confrontational approach that many Americans were demanding.

When it came to actually negotiating with the Soviets, few people in the world boasted more experience or skill at the craft than Ormsby-Gore, who by then had spent three excruciating years across the table from them. He possessed the unique ability to bring seemingly irreconcilable parties to agreement around positions they once thought unimaginable but, through his persuasion, now believed they had a stake in.

A week after the publication of his article, Kennedy invited Ormsby-Gore to spend the weekend with him and Jackie at their home in Hyannis Port. It was not only David’s first visit to the compound, but also the moment when their debate about the role of a leader in a democracy moved to the United States. Ormsby-Gore told Kennedy that Stalin’s recent passing in 1953 had rendered the Soviet leadership more pliable, making worthwhile negotiations possible. In Ormsby-Gore’s view, negotiating wasn’t a tactic out of Chamberlain’s appeasement playbook but a “strategy to bring about the downfall of Soviet Communism.” If Kennedy really wanted to lay the tracks for the Soviets’ eventual demise, Ormsby-Gore argued, the United States must engage with them in disarmament talks. This might have seemed like a counterintuitive argument, but it clicked with Kennedy. As Jackie recalled: “From then on, Jack started to say in his speeches that it was a disgrace that there were less than a hundred people working on disarmament in Washington.”

Leaming, who wrote a biography of Jackie in addition to her account of Kennedy’s evolution as a statesman, later captured how Jackie viewed Ormsby-Gore’s influence over her husband: “Jackie loved in Jack the man he wanted to be, and David was the man helping him, in her eyes, to be the man Jack wanted to be.”

Through the remainder of the decade, both Ormsby-Gore and Kennedy would enjoy meteoric rises within their respective political establishments. In 1956, Kennedy lost the vice-presidential nomination but gained national stature as a rising political star with Hollywood appeal, a rare commodity during a time of gray political personalities.

When Kennedy declared his candidacy for president in early 1960, he made a disquieting discovery about his foreign policy team: Like other young candidates who came before and after him, he found his reputedly wise men either condescending or too fixed in their views to have a meaningful conversation. They most assuredly didn’t align with the Kennedy campaign’s “New Frontier” themes of innovation and imagination. With his relative lack of experience in foreign affairs, Kennedy needed someone with the requisite wisdom, experience, and humility to counsel him throughout the campaign.

And so a scion of British royalty became a highly placed—and highly unofficial—foreign policy advisor to a candidate for the American presidency. Kennedy would call Ormsby-Gore often for quick input on a foreign policy issue, and when they got together in person, said Hugh Sidey, a journalist and Kennedy friend, “The two men were sometimes closeted together for six hours or more completely enraptured by the mutual intellectual challenge of the moment.” In his oral history for the Kennedy Library, Ormsby-Gore recalled one such moment before the Wisconsin primary when they stayed up late into the night talking “arms control and disarmament issues” before the senator flew off to greet workers at a Milwaukee factory gate.
Less than a week after Kennedy’s election, Ormsby-Gore, who was then British minister of state for foreign affairs, formally requested Foreign Office approval to approach the president-elect as a representative of the British government. More than a few officials back in London thought Ormsby-Gore was overreaching and blocked him. What they failed to appreciate was the true depth of the men’s friendship. Before the Foreign Office even made a final decision, Kennedy had silenced their skepticism by reaching out to Ormsby-Gore first. They met a week later for a 90-minute lunch at the Carlyle Hotel in New York.

At 12:20 p.m. on the bitterly cold afternoon of January 20, 1961, John F. Kennedy took the oath of office as America’s 35th president. His inaugural address—one of the shortest in history, at a brisk 14 minutes—stirred the world as he spoke of how “we shall pay any price, bear any burden, meet any hardship, support any friend, oppose any foe to assure the survival and success of liberty.”

There was never any doubt that—at the first opportunity—Prime Minister Macmillan would appoint David Ormsby-Gore to the post of British ambassador to the United States. Both sides saw the urgency and advantages of having so close a friend to the president helping oversee the special relationship between the two countries. Meeting with Kennedy in Key West, Florida, in March 1961, Macmillan asked the president if he had any views on a suitable new ambassador. As Selwyn Lloyd later recalled, the president gave “that dazzling smile of his, like a boy in a toothpaste advertisement,” and said, “I’d like David.” He got David.

Later, reflecting on the outsized influence Ormsby-Gore had on his brother, Robert Kennedy said the ambassador was the only diplomat with whom the president “really had a close relationship at all. My brother would rather have his judgment than that of almost anybody else .…He was part of the family, really.” If anyone doubted that claim, they need only notice the black ambassadorial Rolls-Royce parked most days at the White House.

By the time Ormsby-Gore walked into the White House “unseen” on Sunday morning, October 21, 1962, Kennedy was six days into the Cuban Missile Crisis, with the United States and the Soviet Union eyeball-to-eyeball in a standoff that seemed to be inching terrifyingly close to nuclear engagement. The night before, Kennedy had finally decided on a blockade as the military approach he would take, overruling generals like Curtis LeMay who favored bombing Cuba. Still, the president sought the input and reassurance of the man whose judgment in such situations he trusted most. As Ormsby-Gore later recalled, he had “a pretty good idea of what was already happening” from the CIA reports shared with the British, but he knew none of the particulars.

Unlike during the embarrassing debacle of the Bay of Pigs a year and a half earlier, when the president could not keep his friend informed of U.S. plans, the president this time eagerly filled-in Ormsby-Gore on all the details of the looming showdown. He shared satellite photos of the missile sites, then laid out the bombing or blockade options that had been presented to him. Measured and thoughtful, Ormsby-Gore argued for a blockade, believing bombing would only escalate matters. The rest of the world wouldn’t understand such overt aggression, he said, and it would also likely compel the Soviets to move against West Berlin. But Kennedy countered: Isn’t this our best chance to take the strongest possible action to deter Castro from ever trying to do this again?

The conversation went back and forth this way for an hour. In unusually passionate language, Kennedy declared that the mere existence of nuclear weapons made “a secure and rational world impossible.” Ormsby-Gore had rarely heard his friend speak so openly and emotionally. Perhaps all their discussions around test bans and disarmament had taken root, Ormsby-Gore thought. Later that night, when he and his wife, Sissie, returned to the White House for dinner, the president and Ormsby-Gore continued to debate the language that Kennedy should use to announce the blockade to the American people the following evening. The decision had been made, but Kennedy was still agonizing over it.

Two nights later, the Ormsby-Gores and other British friends from their WWII days returned to the White House for a long-planned dinner with the president and Jackie. The poignancy of the moment wasn’t lost on any of them. A quarter century before, they had shared similar meals, wondering whether bombs would soon be raining down on them. At the end of the dinner, with Soviet ships fast approaching the quarantined zone, the president excused himself and took Ormsby-Gore to the Long Gallery to further strategize the imminent showdown.

Over brandy and cigars, the two men began discussing how poorly Kennedy’s speech the night before had been received in Europe. The president had declared that the launch of Cuban nuclear missiles on any nation in the Western Hemisphere would be viewed as an attack on the United States, requiring a swift and full retaliatory attack on the Soviets. Ever suspicious of the CIA, Europeans remained deeply skeptical over whether the Soviet missiles were as threatening as Kennedy described or even existed in Cuba at all.

Ormsby-Gore offered a solution: Why couldn’t the United States release some irrefutable evidence such as U-2 photos of the missile sites? Intrigued, Kennedy asked for photos to be brought up to him. Jackie later recalled walking in on the two men “crouched on the floor” looking at satellite pictures, trying to determine the best ones to release. And when they were made public the following day, each photo included a “clear explanatory” note—just as Ormsby-Gore had recommended.

After resolving this problem, Kennedy told Ormsby-Gore that his brother Bobby had learned earlier in the evening about the Soviets’ plans to have their ships “go on to Cuba” right through the blockade. That news led Ormsby-Gore to question the current perimeter of the quarantine zone itself.

Looking at a map that put the zone at 800 miles from Cuba’s shoreline, Ormsby-Gore asked the obvious question: Was that the right point to intercept the Soviet ships? Without any instructions at all from his government, Ormsby-Gore began to argue “rather strongly” that the perimeter needed to be shifted closer to Cuba “to give the Russians a little bit more time” to consider the gravity of breaking the blockade. Intrigued again, the president called Defense Secretary Robert McNamara and asked why the perimeter had been set at its current point. The answer Kennedy received—if the perimeter was moved in closer, Cuban planes would be able to intervene in any confrontation—failed to satisfy him. He pushed back.

That night, the blockade line changed to 500 miles, exactly the distance that Ormsby-Gore advised. As important as Ormsby-Gore thought it was to give the Soviets the extra 300 miles to turn back, however, he reinforced to Kennedy the importance of showing resolve. Vienna still weighed on both men’s minds. If Khrushchev had any inkling that he could bully the president, the situation would prove “disastrous,” Ormsby-Gore reminded him.

That night and throughout the 13 days of the crisis, Kennedy obsessed over every strategic detail. At some point, Ormsby-Gore recalled a particular concern the president suddenly raised: What if all the military aircraft massing in Florida were “drawn up in their usual lines” and the Cubans decided to strike? They could all be knocked out by just one Cuban fighter strafing down the line. With painful memories of Pearl Harbor still fresh two decades later, Kennedy wasn’t going to let that mistake be repeated under his command. Getting on the phone again with McNamara, he asked for a photo-reconnaissance flight to ensure the dispersal of the planes. “No need,” McNamara assured the president, “they’ve already been scattered.” Kennedy insisted on double-checking. “They flew over and all the planes were in line up and down the runway,” Ormsby-Gore later recounted.

Ormsby-Gore would remain a presence at the White House for the next six days. His proximity to the seat of power did not go unnoticed. Vice President Lyndon Johnson complained that “the limey” was seated “front and center” at a meeting of a steering group that week in the White House Situation Room, while he himself was “down in a chair at the end, with the goddamned door banging in my back.” Afterward, Jackie described Ormsby-Gore’s presence then and later as “indispensable,” adding: “If I could think of anyone now [after Jack’s death] who could save the Western world, it would be David Gore.”

With Ormsby-Gore’s counsel, Kennedy stared down Khrushchev, and this time he didn’t blink, securing a settlement that eliminated the offensive Soviet missiles from Cuba in return for a guarantee—not made public at the time—that the United States would remove its own missiles from Turkey. When the crisis had passed, Ormsby-Gore sent a handwritten note to the president expressing his “admiration for the superb manner” in which he conducted himself throughout the crisis despite the “mass of conflicting advice you received.” Kennedy kept the letter in the Resolute Desk in the Oval Office for the remainder of his life.

It wasn’t the only major foreign policy decision that Ormsby-Gore helped Kennedy make.

Within two months of resolving the Cuban Missile Crisis, Kennedy turned to Ormsby-Gore again, this time to help him chart a path that would lead to a limited nuclear test ban treaty between the U.S. and the Soviet Union. It was an issue Ormsby-Gore had pursued for the past 12 years and knew more about that most any other foreign policy specialist in the world. Calling for a final time on their 25-year debate over what a leader owed his constituents, Ormsby-Gore ultimately prevailed in overcoming Kennedy’s reluctance to sacrifice any of the political capital won earlier in Cuba. Using all of his powers of persuasion, Ormsby-Gore converted Kennedy into the evangelist-in-chief for a treaty that would mark the beginning of the end of the Cold War a generation later.

By mid-1967, Jack had been assassinated and Sissie had died in a car crash.

After Sissie’s death, Jackie and Ormsby-Gore’s friendship deepened as they sought consolation in their mutual bereavement. Correspondence between the two, saved by Ormsby-Gore in two locked dispatch boxes only discovered three years ago, revealed that the friendship culminated in Ormsby-Gore asking Jackie to marry him. Gently deflecting the proposal in October 1967, Jackie wrote Ormsby Gore that she couldn’t be involved with anyone who so directly reminded her of Jack. A year later, she stayed true to her word (if shocking the world) by marrying the Greek billionaire Aristotle Onassis. Forlorn but determined to move on himself, Ormsby-Gore too would find a new spouse not within his prior world. In 1969, he married Pamela Colin, an American magazine editor.

But suffering would never escape him. Over the next 20 years, two of David and Sissie’s children would also suffer tragic deaths: Their oldest son, Julian, would die from gunshot wounds, an apparent suicide, in 1974; and in 1985 their daughter Alice, who was engaged to guitarist Eric Clapton, died of a heroin overdose. Their two remaining daughters, Victoria and Jane, survive. Jane was rumored to have had an affair with Mick Jagger (all she will acknowledge today is that they are “great friends”), and most still consider her the inspiration for the Rolling Stones song “Lady Jane.” His second son, Francis, became the sixth Baron Harlech and sat in the House of Lords until 1999. He died in 2016.

On a winter night in January 1985, David Ormsby-Gore—Lord Harlech—crashed his car while driving over Montford Bridge in Shropshire, England. He had spent his final full day interviewing potential Kennedy scholars who hoped to attend Oxford under a program Ormsby-Gore had helped create and endow after Jack’s death. He died the following morning in a nearby hospital—eerily killed just as his brother and wife were. He was 66 years old.

His funeral and burial were held in the tiny parish of Ardudwy, Gwynedd in northwest Wales, home to the Harlech barony. Among the 90 family and friends who crowded into the small church to witness his funeral were Jackie Kennedy Onassis and Senator Edward Kennedy. During the service, the Reverend Robert Hughes eulogized Ormsby-Gore as “a citizen of the world, equally at home in the fertile beauty of Shropshire, the sophistication of London or the special jungle of international diplomacy.” Afterward, Ted Kennedy remembered Ormsby-Gore as “the most intelligent man he had ever known.” Jackie Onassis reportedly fought back tears as she left the burial.

It marked the final verse in a long and very special friendship between John F. Kennedy and David Ormsby-Gore, perhaps best described in the words of Percy Shelley, whose book of poetry Jackie had given to Ormsby-Gore shortly after JFK’s death:

Friendship…a dear balm. A smile among dark frowns; a beloved light:

A solitude, a refuge, a delight.

From the book FIRST FRIENDS by Gary Ginsberg. Copyright © 2021 by Gary Ginsberg. Reprinted by permission of Twelve, Hachette Book Group, Inc., New York, NY. All rights reserved.

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