A Special Relationship

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 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 ninety 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 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 speech the following evening. The two men recognized that 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 employ the next night. Then, over the six days and nights following the address, Kennedy and Ormsby-Gore would draw deeply on their twenty-five-year conversation 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 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.

Bundy, Kennedy’s national security advisor, 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.

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 forty-six 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.

Kennedy had what historian and presidential advisor Arthur Schlesinger Jr. called “the gift of friendship.” His world was filled with friends culled from every aspect of his life—his family, the elite schools he attended, the Navy, and even his extensive travels abroad. His speechwriter Ted Sorensen said the perfect Kennedy friend was someone “cheerful, amusing, energetic, informed and informal.” He gravitated toward those who could make him laugh and, in particular, execute a sophisticated prank. Kennedy himself loved to prank, and he never stopped even when he got to the White House. With his love of quick banter and good jokes, Kennedy also thirsted for gossip, the more salacious the better, especially when it concerned the affairs of politicians, reporters, and friends that he could then mischievously trade for more. “Who does Castro sleep with?” the president once asked a stunned journalist from Look. “I hear he doesn’t even take his boots off.” Above all else, Kennedy cherished loyalty. He returned that loyalty by giving his friends unfettered access to his life of glamour, action, and purpose.

As open to friendship as he was in his personal life, Kennedy was equally wary of it in his public life. He served in Congress for over half of his adulthood, yet in those fourteen years, with the exception of George Smathers of Florida, he never forged a single real friendship among his fellow House members or senators. Reflecting on this oddity after his death, Jackie believed he subscribed to the Palmerston theory, which held that in politics there are no permanent friendships or alliances, only permanent interests. Whether consciously or not, Kennedy realized early on that to get overly invested in politicians was a waste of time, because interests shifted daily. A friend one day could become a foe the next. So he preserved his equanimity by keeping his personal distance from Hill colleagues.

Much like how the New York Times Magazine would depict Bill and Hillary Clinton’s lives a generation later, Kennedy’s vast world can be visualized as a galaxy of individual planets rotating around a single sun.

The planet that orbited closest to him was his immediate family: his parents, Joe Sr. and Rose; his three brothers, Joe Jr., Bobby, and Teddy; and his five sisters, Kathleen, Eunice, Rosemary, Pat, and Jean. From their birth, Joe Sr. had instilled in all of his children a fierce protectiveness of the family, which fostered a closeness among them that would last their lifetimes. But, as in any family, Jack had his favorites. He bonded most easily with his oldest sister, Kathleen, known to all as “Kick,” though the sibling he would ultimately be closest to was his younger brother Bobby. To those who knew the brothers growing up, it wasn’t always obvious this would be the case. Jack was eight when Bobby was born. Slight of frame and small in stature, Bobby was described by his father as the “runt of the litter,” while his mother worried he would grow up to be a “sissy.” On the contrary, he matured into a highly skilled and ruthless political operative who, starting from 1952, would manage every one of Jack’s campaigns. Few would deny that “as much as any single person alive, it was Bobby Kennedy who made Jack Kennedy president.” As president, Kennedy would rely on his brother—the country’s youngest-ever attorney general—for counsel on every major decision he made.

Lem Billings occupied his own planet. He visited the White House so often that, depending on the source, he was either given his own room or at the least allowed to keep his belongings in a third-floor guest room. Kennedy’s sister Eunice described Lem’s friendship as a “complete liberation of the spirit” for her brother, who especially delighted in the elaborate practical jokes he could play on Lem. In the summer of 1962, Billings became fast friends with the actress Greta Garbo. He came back to the White House filled with details of their enchanted adventures across Europe. Immediately inspired, the president soon invited Garbo to the White House for an intimate dinner with Jackie and her new close friend Lem. Garbo arrived first and spoke with the president, who gave her special instructions for the evening. Then Lem came in, “glowing with anticipation,” and opened his arms: “Greta!” A ghastly pause followed. Garbo looked at Lem blankly. She then turned to the president and said, “I have never seen this man before.”

The next half hour was excruciating for Billings. He rattled off all the places they had visited, the friends they had met, and the meals they had shared. Nothing worked. Embarrassed and befuddled, Billings never considered the possibility that her amnesia was contrived by none other than the president. The actress kept up the ruse until the second course. Later, Billings would remember the dinner as “one of the worst things I ever went through in my life.”

Next came the “Irish mafia,” most notably Dave Powers and Kenny O’Donnell, both fiercely loyal men who met Kennedy in the 1940s and would serve him unflinchingly until the last day of his life. There were also his Navy friends, men like Red Fay and James Reed, who experienced the crucible of the Second World War with him and lived to tell, and retell, their heroic exploits.

And then there were the intellectuals, men like Schlesinger, Bundy, and speechwriter and aide Ted Sorensen, who quenched the president’s thirst for knowledge. Schlesinger and Bundy managed to straddle the worlds of ideas and glamour, and they typically made the cut of the most sought-after social invitations. Sorensen with rare exceptions didn’t get invited, a rejection that rattled him. Jackie Kennedy later admitted she kept him away because of the persistent rumors—rumors she blamed Sorenson for instigating—that he was the real author of Profiles in Courage, the book that won Kennedy a Pulitzer Prize for biography in 1957. Worse, she acknowledged what every socially ambitious staffer in the White House feared most: “As [Jack] and Ted had the problems all day, that would be the last person you would invite at night.”

And finally there were his friends from the press, such as Ben Bradlee, Charlie Bartlett, and Joseph Alsop, who amused the president with an intoxicating blend of gossip, tales of backroom machinations, and the skepticism that came from having spent their careers covering Washington politics. Of the three, Bradlee came to the party the latest but grew closest to him during his presidency. Kennedy loved to gossip—according to Bradlee, “It was one of his all-time favorite subjects.” Blessed with Kennedy’s good looks and as clued-in as anyone, Newsweek’s DC bureau chief never failed to satisfy the president’s need for the latest buzz.

Out of Kennedy’s numerous friends, only one transcended all these groups—able to move seamlessly among family and staff, around the intellectuals and the media luminaries, with the Irish crowd and the Navy pals. Kennedy himself seemed to recognize this adaptability when he described Ormsby-Gore as “a companion for every mood.”

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.” David 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.

Kick Kennedy’s entry into polite British society in the early spring of 1938 was proving far more difficult than she had ever anticipated. The eldest daughter of America’s brash new ambassador to the UK, she arrived shortly after her eighteenth 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 twenty. 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. Though innately shy, Ormsby-Gore in the right environment was a man who loved to talk—and then talk some more. That evening, armed with knowledge derived from a youth spent reading, David, his first cousin Andrew Devonshire, and his friend Hugh Fraser regaled Kick with their quick minds and wit; and Kick, enchanted and amused, reciprocated with equal verbal velocity. 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 David Ormsby-Gore, Andrew Devonshire, Hugh Fraser, and many others, 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 twelve books on the subject weekly), and now his father was the US 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 shared 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. Both were good-looking, though David in a less classic sense. Toothy and angular, with a prominent nose and a shock of black hair, David didn’t possess the chiseled features of his friend Jack, but he more than compensated for it with a debonair, confident style. Both liked to have a good time. When they weren’t on dates squiring women around London, they were often together—either on the golf course, at the racetrack, or in underground nightclubs, engaging in spirited conversations that typically included a fair amount of drinking (mostly by David) and gossip. Their speaking styles and sensibilities suited one another as well: Jack, easily bored, wanted to get to the point; David also talked fast, with plenty of color and wit. 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 twenty-five 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 twenty 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 Barbara 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. Whatever early doubts she had about her suitability to blend into the city’s rarefied social scene had long since abated. To the contrary, she now blossomed at its center. She had fallen in love with David’s best friend and first cousin, Billy Hartington, himself a lord-in-waiting to one of England’s most important dukedoms and one of London’s most desired bachelors. Given the taboo then against marriage between Catholics and Protestants, their families both fiercely objected to the romance—but to no avail. David, a Protestant, also fell in love at roughly the same time to a Catholic, 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.

The London that Jack returned to in mid-1939 was a changed city from the one he had left the previous fall. The fear of imminent war with Germany was as pervasive as the resolve of young Brits like Billy and David to serve when war arrived. Billy by then had enlisted in the Coldstream Guards, an active frontline regiment. David wanted to do the same but was blocked by his father, who feared losing another son. Instead, David joined the Territorial Army where, as his father hoped, he would likely never see combat.

As sentiment among his children’s friends grew for a muscular response to German provocations, Ambassador Joe Kennedy continued to insist that Britain would be annihilated if it went to war. One evening that summer, Kick invited David, Billy, and a few other friends to dine with her father and Jack at the embassy residence. After dinner, as he often did, the ambassador decided to show a movie. The former Hollywood studio owner typically would screen a light movie. This night, he had a different objective in mind; entertainment wasn’t it. He showed instead a movie about the horrors of war, with World War I as his example. Soon his guests were viewing some of the most gruesome images from the Great War. Joe Kennedy’s intent couldn’t have been more obvious. “That’s what you’ll all be looking like in a month or two,” he shouted, as scenes of British soldiers being mowed down played before their eyes. But if he had hoped to convince the young men of the folly of war, his one-man show actually accomplished the opposite. Their British reserve kicked in—none made a fuss—but Kick, noticing their displeasure, later apologized for her father’s insensitivity. Jack “sat impassive throughout,” never uttering a word of opposition to his father’s diatribe. If he was embarrassed by his father’s intemperance, he wasn’t going to display it to outsiders, even those as close as David and Billy.

By then Jack was much more of a realist about the likelihood of the British going to war than his father, observing the rise of German militarism with the same cool detachment that would later characterize his approach to other moments of crisis. With David in tow, he went to Germany in the late summer of 1939 to assess the situation for himself, and he concluded that war was fast becoming inevitable. He suspected that Hitler was badly misjudging Britain’s resolve—this time to fight, not appease. On September 1, 1939, the Germans finally tested that resolve by invading Poland. When the British, as Jack predicted, honored their pact with Poland and, joined by France, declared war on Germany two days later, armed conflict again swept across the world.

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. As the German blitzkrieg rained missiles all around him in London, Kennedy sent cable after cable back to Washington predicting England’s demise and urging the United States to stay neutral. The more he advocated for isolationism, the more isolated he himself grew from President Roosevelt and the State Department. By the summer of 1940, it was clear he needed to go; when Roosevelt won reelection to a third term that fall, Joe Kennedy resigned in disgrace.

Of all the Kennedy children, Kick had put up the biggest fight to remain in London when her father moved the family home. By 1943 she finally prevailed, returning into the arms of Billy Hartington despite threats from her mother that she would disown her. In May 1944, the two were married in a small civil ceremony. The only Kennedy to attend was her brother Joe.

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 twelve crewmates, ten 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.

But the war would also bring tragedy to both families. In the late summer of 1944, Kennedy lost his older brother, Joe, when the plane he was piloting blew up over East Suffolk, England. His father took the loss especially hard. According to one of his closest friends, Arthur Krock, Joe Kennedy was overwhelmed not only by grief, but also by guilt. In Krock’s retelling, Joe came to believe that his son took on the dangerous mission that killed him not to outdo his younger brother’s heroics, as most assumed, but to disprove the image his father had created of the Kennedys as cowards and capitulators. Then, just three weeks later, Jack lost his brother-in-law and Ormsby-Gore his best friend and first cousin when Billy Hartington was killed by a sniper in Belgium. In rapid succession, the two men suffered terrible loss. In time, however, they would come to mitigate these losses through their own enduring friendship.

With the war finally over, a saddened but newly motivated Jack Kennedy returned to London in the spring of 1945, his first visit in six years. Though still gaunt from his serious war injuries, Kennedy eagerly delved into his new work as a journalist for the Hearst Newspaper Group, assigned to cover the British general election pitting the war hero Churchill against Labour Party leader Clement Attlee. Most afternoons when he returned from reporting, he would hole up in his Grosvenor Hotel suite, where Ormsby-Gore and a few other British friends would join him for drinks and spirited political debate. To perceptive friends like Ormsby-Gore, it was clear Kennedy was observing the campaign as much “with an eye to his own political future” as to how the British would vote (they shocked themselves—and the world—by voting out the war hero). The overwhelming impression Ormsby-Gore and others had of their American friend was that he had become a grown-up—a more serious, sober, and substantive man than the one they remembered.

Soon the newly reunited men fell right back into their familiar patterns of rapid-fire gossip. As close as they were before, the two friends were now even more solidly bonded as a result of Billy Hartington’s death. After his passing, David and Sissie deepened their relationship with both Kick and, by extension, Jack. To David, Jack became another “cousin” to be counted among their large clannish family, which in the world of British aristocracy was “no small matter.”

One reason Jack’s friends suspected he was eyeing a political future was the opening that came with his older brother’s death. While shattering, Joe’s death was also liberating, freeing Jack to pursue a political career once thought reserved only for the eldest son. In truth, Jack had never been especially close to his older brother, and they often competed for the spotlight. At a fifty-fifth birthday party for Joe Kennedy Sr. two years earlier, a close friend, after toasting the guest of honor, had offered a second toast to the absent ambassador’s second son, “our own hero, Lieutenant John Kennedy of the United States Navy.” Ignored was Joe Jr., seated right next to his dad and who in mere days would himself set off for war. Later that night, the snubbed son was heard sobbing in his bed: “By God, I’ll show them.” Now, in Joe’s absence, Ormsby-Gore could sense from those late-afternoon talks Kennedy’s ambition to emerge from his brother’s long shadow.

Ormsby-Gore, on the other hand, remained as baffled about his future as he had been in 1938. The war years had given him a family but not a career. “I hadn’t got a clue what I wanted to do in life,” Ormsby-Gore later reflected on these postwar years. While other close friends were standing for seats in the Commons, Ormsby-Gore defaulted to spending time with his father learning how to manage the family’s estates.

Ormsby-Gore’s observation about Jack’s political aspirations was prescient. Returning home that fall, Kennedy decided he would rather shape events than cover them as a journalist. He carefully weighed several potential races before deciding to run for an open seat in Congress from his hometown of Boston. Despite having left the city almost twenty years earlier, his family still maintained strong political connections to the district. Jack put that network—and his father’s fortune—to immediate use, bombarding the district with paid advertising and get-out-the-vote efforts while enlisting his sisters to organize teas for female voters dazzled by the handsome young war hero. He was a patrician candidate campaigning in the blue-collar saloons and docks of a district that should have been repelled by his family and his wealth. Yet in a field of ten that included two prominent longtime Boston pols, Kennedy outhustled and outsmarted his competitors, convincing skeptics that he had the grit, guts, and substance to represent their interests in Congress. On primary day he won handily, doubling the vote total of his next closest competitor. In the general election he won in a rout. Observing Kennedy’s success, Ormsby-Gore found it both “fairly remarkable” and “impressive and somehow a little difficult to take seriously”—reactions perhaps as much tinged with envy as with memories of their cavorting through London as carefree youths.

Even in good times, however, tragedy never seemed far away. By 1948, Kick had fallen in love again, this time with Peter Fitzwilliam, a soon-to-be-divorced Protestant aristocrat she planned to marry—again over her parents’ strenuous objections. On May 13 of that year, the couple was flying from Paris to the Riviera when their storm-tossed plane went down into the hills of the Rhone Valley, killing them instantly. Kick Kennedy was only twenty-eight years old. Her death left Jack so distraught that even after he had flown to New York to board the plane to her funeral in England, he couldn’t summon the strength to continue the trip. Shattered themselves, Ormsby-Gore and his wife were among the mourners. Six weeks after Kick’s passing, Jack finally made the trip to London to tend to her affairs. When the moment came to visit her grave, he still couldn’t leave London to do it.

“True freedom means pushing oneself to the full all the time, always knowing of one’s approaching end,” Kennedy wrote to Ormsby-Gore later that spring.

Jack’s electoral success coupled with Kick’s sudden death seemed finally to shake Ormsby-Gore from his decade-long lethargy. In 1950, he won a seat in the House of Commons—almost by accident. Filled with ambivalence, Ormsby-Gore had taken 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 US-UK alliance, could act as an effective bulwark against an expansionist Soviet Union. They would translate that shared conviction 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, thirty-five-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 US 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. Poor decisions by leaders in the past could cost millions of lives. Poor decisions today might imperil “the very existence of mankind.” Consequently, Kennedy argued, the duty of a leader was “not to pander to people’s false beliefs in an effort to win votes, but rather to take steps to educate and enlighten public opinion.” 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 then 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 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 that Jack’s “twenty-five year conversation with British friends shifted to American soil.” 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.”

Kennedy would return to the issue of disarmament many times in the future, but first he had pressing health concerns to address. Despite appearing vigorous and healthy, Kennedy at thirty-seven was anything but. Ever since childhood, Kennedy had battled debilitating health conditions that often required extensive stays in hospitals. Never showing a hint of his struggles in public, Kennedy at various times suffered chronic pain borne of a degenerative back, Addison’s disease, and severe intestinal ailments. Now in 1954 he was facing his second back operation in a decade, this time a delicate spinal fusion. Ormsby-Gore went to New York with Jack and Jackie for the surgery. In one of the pre-op meetings, with Ormsby-Gore by his side, the doctors told Kennedy he had a fifty-fifty chance of surviving the procedure. “I’d rather be dead than spend the rest of my life hobbling on crutches and paralyzed by pain,” he told his friend.

Kennedy survived the surgery, barely, coming so close to death that a priest came to perform last rites. After yet another operation and then a long recuperation, Kennedy regained enough strength to travel back to England the following year.

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. His constant health battles had one decided upside: With so much time spent on his back convalescing, Kennedy could write his Pulitzer Prize–winning book, which brought him additional fame and gravitas. In many ways, Profiles in Courage was a paean to Churchill’s conception of leadership. Meanwhile, Ormsby-Gore also experienced his own notable run of professional success, having been promoted to replace Lloyd as minister of state.

Kennedy and Ormsby-Gore took full advantage of each other’s growing prominence, consulting on crises and acting as sounding boards for one another. During Kennedy’s successful Senate reelection campaign in 1958, he used the race to test out themes he and Ormsby-Gore had been debating for twenty years. Comparing President Eisenhower to Baldwin a generation earlier, Kennedy argued that Eisenhower had wasted the last several years while the Soviets rebuilt their military capabilities. The result, he warned, was an imminent “missile gap” in which the United States would lose its nuclear superiority. His appropriation of Churchill’s pre–World War II rhetoric helped him win an overwhelming victory and notice as a formidable new national candidate.

By 1959, as Kennedy contemplated launching a bid for the presidency, Ormsby-Gore began sharing details of his continuing talks with the Soviets about ending nuclear weapons testing. Kennedy understood it wasn’t enough just to fearmonger over a looming “missile gap”: He also had to offer Americans a practical solution. He began pressing his friend on how such a treaty limiting arms could be achieved. Ormsby-Gore responded with a memorandum laying out in detail the process and substance by which the United States could secure a historic agreement. It so resonated with Kennedy that it became a standard talking point in his writings and speeches. By combining tough talk now with diplomatic outreach, Kennedy could present himself as a hawk who would nonetheless pursue a realistic path to peace. In typical understatement, Ormsby-Gore recalled his influence on Kennedy’s “carrot and stick” approach: “I noticed in certain speeches… that he did make it quite a theme.”

Later that year, Kennedy made another trip to Britain, during which he had his first face-to-face encounter with one of his heroes, Winston Churchill. Ironically, the meeting took place on Aristotle Onassis’s 325-foot yacht Christina, on which Kennedy’s widow nine years later would live for months at a time as Onassis’s wife. That night, Kennedy wore a tan mess jacket with a black tie. Churchill by then was showing signs of aging, physically and mentally, and often failed to recognize even prominent people. One witness recounted that as the Kennedys were leaving, Jackie half-kiddingly told her star-struck husband, “I think he thought you were the waiter, Jack.”

Once 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. Dave Powers later remembered how the bone-weary candidate, with no sleep and one bad cup of coffee, still managed to shake every last hand. Kennedy won the primary and went on to sweep enough of the remaining contests to secure a first-ballot victory at the Democratic National Convention in Los Angeles that summer.

As the general campaign unfolded, Ormsby-Gore kept Kennedy abreast of developments in arms talks and provided sharp insight into the status of Soviet military might. He confidently told Kennedy that the Soviet nuclear arsenal did not exceed that of the United States, as Kennedy himself knew. But Ormsby-Gore also realized that the so-called missile gap remained a politically potent issue among American voters, and so he was willing to overlook his friend’s bending the truth to gain electoral advantage. By constantly invoking the “missile gap” and vowing to surpass the USSR in nuclear capabilities, Kennedy could thwart the efforts of his Republican opponent, Richard Nixon, to paint him as soft on communism.

And that is what he did, reprising the strategy he so successfully employed in the 1958 election. In effect, Kennedy channeled the Churchill of the 1930s, even employing the words “locust years” as he called for America to rearm. But this time he coupled his bellicosity with language promising he would also pursue diplomacy to achieve a breakthrough arms control treaty. Guided by Ormsby-Gore’s astute offstage counsel, Kennedy managed to thread the needle and find a way to present himself as the candidate of both peace and military strength.

It was deft messaging, and it worked. Kennedy edged Nixon to become America’s youngest-ever elected president, at the age of forty-three years, 236 days. Less than a week after Kennedy’s election, Ormsby-Gore as minister of state 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 ninety-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 thirty-fifth president. His inaugural address—one of the shortest in history, at a brisk fourteen 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.” The new president’s British friends, those who had known him back in the summer of 1938, expressed the most astonishment. “It was as though one had gone to sleep knowing Jack as a charming young student or promising political apprentice and woken up to find him the most powerful man in Christendom,” Selwyn Lloyd marveled.

The President and Ormsby-Gore had his first extended sit-down five weeks after the inauguration. Over dinner in the residence of the White House, Kennedy told Ormsby-Gore of the four consequential foreign policy decisions he would soon have to make—all leftovers from the Eisenhower administration. To frame and then address these issues, he and Ormsby-Gore returned to their familiar paradigm: choosing between boldness and caution.

This night, however, Kennedy had ample reason to feel emboldened: He had just learned that his approval ratings after his first month in office were four points higher than Eisenhower’s at a comparable period. The question Kennedy now debated with Ormsby-Gore was whether to use that popularity to do what he thought right: admit Communist China into the UN and not support the anti-communist forces fighting in Laos—positions he knew Eisenhower and a majority of the public opposed. Carefully weighing both sides with Ormsby-Gore reassured Kennedy his instincts were right. He would delay a decision on China while remaining neutral on Laos. As the men continued to talk past midnight they also agreed that the upcoming nuclear test ban talks held the promise of a groundbreaking treaty both desperately sought.

There was one topic, though, that Kennedy could not be forthcoming about: what he planned to do in Cuba, where communist Fidel Castro had led a successful revolution two years earlier. The president was weeks away from approving a flawed invasion plan in which the CIA would dispatch fourteen hundred half-trained Cuban exiles to the Bay of Pigs to topple Castro’s regime. That night he could only hint at the troubles he faced, since Ormsby-Gore was a British official. Despite the president’s absolute trust in his friend, even their friendship faced hard limits when it came to the CIA’s clandestine operations. So Kennedy had to conceal his profound doubts about Eisenhower’s leftover Cuba team and the poorly planned scheme he would soon authorize. One can only speculate that had Kennedy enjoyed the benefit of Ormsby-Gore’s informed judgment, history might have turned out differently. Instead, in April 1961, twelve hundred American sympathizers were either killed or captured on the beaches of Cuba, dealing Kennedy a humiliating loss.

Two months later, heavily medicated for his back pain and other ailments and demoralized by the Cuban debacle, Kennedy had his first meeting with Soviet leader Nikita Khrushchev. At his February dinner with Ormsby-Gore, Kennedy had raised the idea of an informal summit with Khrushchev as an opportunity for the two men to get to know one other. Wary from years studying the combative Soviet leader and negotiating with his team, Ormsby-Gore bluntly told Kennedy the idea was “premature” and bound to fail: Khrushchev wasn’t one for small talk and would want to use the time, whatever the president’s intentions, to press his own agenda.

Ormsby-Gore proved right. The Vienna summit was a disaster by all accounts, including the president’s. “Worst thing in my life,” he vented to a New York Times reporter. “He savaged me.” Kennedy felt browbeaten and belittled, and he left Vienna convinced Khrushchev thought him weak and America vulnerable. By the time he got to London, Kennedy looked “worn out,” remembered Ormsby-Gore. Before beginning his official duties, the president and First Lady went to Jackie’s sister’s home near Buckingham Palace. There, among a few of Kennedy’s London intimates, Ormsby-Gore found his friend in “great pain.… There is no doubt that Khrushchev made a very unpleasant impression on him. That’s what he said to me.… That Khrushchev obviously tried to browbeat him and frighten him. He had displayed the naked power of the Soviet Union.”

The next morning Kennedy was scheduled to meet with Prime Minister Macmillan and his senior advisors. The avuncular British leader immediately sensed the president’s distress. As the American motorcade pulled up to the Admiralty House, according to notes taken of the moment, Macmillan took one look at Kennedy, put his arm around his shoulder, and, scrapping the larger meeting, took him upstairs for a private chat that would last two and a half hours. Despite the early hour, the prime minister offered him a stiff drink—“which was accepted.” At the president’s request, Ormsby-Gore joined the two leaders at the end of their marathon talk, and he later described the one-on-one meeting as “the beginning of a much closer understanding” between the two leaders and a stronger relationship between the two countries.

In the early afternoon, the president put aside his physical and emotional pain to lunch with Ormsby-Gore and various other British friends. Afterward, the president and his friend talked alone, deliberating on how to position the failed Vienna summit the next night in Kennedy’s address to the American people. The president was determined not to repeat the mistake Chamberlain had made in 1938 when he returned from Munich to famously and falsely proclaim “peace for our time.” Ormsby-Gore urged him to speak with complete candor, telling the nation the hard, unpleasant truths that he had learned from Vienna and not to sugarcoat anything. Kennedy agreed. The next night, when Kennedy delivered the address, he struck a notably subdued tone, telling the American people of a “very sober two days” during which no progress had been “either achieved or pretended.”

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.

At Ormsby-Gore’s White House investiture six months later, Kennedy happily expressed what everyone in the room knew to be true: his great pleasure at the United Kingdom’s decision to “appoint you, an old friend, as her representative.” Almost immediately, Ormsby-Gore became, in Macmillan’s words, an “invigorating new spirit” in the Atlantic alliance. Not only did no other ambassador in Washington have a closer relationship to Kennedy; no senior White House, State Department, or Pentagon officials did either—much to the dismay of Secretary of State Dean Rusk, who complained the president saw more of “that man” than any of his own top advisors.

This closeness benefited both men. In December 1961, Kennedy and Ormsby-Gore met for one of many private dinners over the course of Kennedy’s thousand days in office. As they settled into their seats, Ormsby-Gore told the president that he had just heard from Macmillan that the British government could fall if the UN continued to threaten sanctions against British-backed troops in the Congo. Without delay, the president picked up the phone and called both the State Department and his UN ambassador to request a total reversal of US policy in the region. “I have got David Gore sitting beside me here. He will explain what it is the British government wants done, and I want it done,” he told them. By the next morning, the threat of sanctions was lifted. The Macmillan government held.

Kennedy could possibly afford to be generous to his friend because at that moment no vital US interest was at stake in the Congo. Nevertheless, as Ormsby-Gore later said, the president was “wonderful. He threw the full weight of his authority behind getting the results that [we] required.”

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 Bay of Pigs, 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—along with Andrew Devonshire and his wife, as well as two other British friends from their World War II 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 “squatting 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 eight hundred 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 five hundred miles, exactly the distance that Ormsby-Gore advised. As important as Ormsby-Gore thought it was to give the Soviets the extra three hundred miles to turn back, he nevertheless 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 thirteen 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 photoreconnaissance 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.

With Cuba behind them, the two friends shifted their focus back to a nuclear test ban treaty—the single best way in their minds to deescalate a Cold War that might drive the world to extinction. Their first hopeful sign that after the fits and starts of the previous twenty-four months a pact could now be achieved came while they were vacationing in Palm Beach with their families just before Christmas in 1962. The Soviet premier sent a letter indicating his willingness to negotiate not just a test ban treaty but one with verifiable inspections. Kennedy and Ormsby-Gore were jubilant. Just three months earlier, they had barely averted a nuclear war. Now in mid-January 1963, they were starting bilateral negotiations in New York to rein in those very weapons. A week later, with Kennedy’s approval, Ormsby-Gore joined the talks as the British observer, and work got underway. That very day, in a signal to the Russians of his full commitment, Kennedy postponed already scheduled underground nuclear tests for up to three weeks while the negotiators met.

That single move proved to be a bridge too far for those still skeptical of the Soviets’ intentions. As soon as Kennedy postponed the tests, Republicans began to attack him for appeasement. The most stinging criticism came from the one Republican he most feared politically—New York governor Nelson Rockefeller, who said Kennedy’s concessions “threatened the future security of the U.S. and the world.” The adulation that had enveloped Kennedy after the missile crisis—the resolute, confident leader who stood up to the Commies—soon gave way to fears for his reelection in 1964.

Kennedy and Ormsby-Gore retreated to Palm Beach in late February 1963 to assess the president’s quandary. Kennedy, convinced that a treaty with the Soviets would not survive a Senate vote, was not willing to take on a major political risk that might threaten his electoral prospects—no matter how much he believed in the treaty’s merits. A shaken Ormsby-Gore used every argument he could to move Kennedy away from his Baldwin-like mindset, but for once his efforts seemed futile.

One man who emphatically would not give up, however, was Prime Minister Macmillan. Having seen the horrors of world war firsthand, he refused to let the chance of averting an even more deadly one elude him. The prime minister grasped, even appreciated, the political risks Kennedy faced in advocating for the ban. But he nonetheless believed this was the moment to take such a risk. Ensuring peace, Macmillan believed, was too important to be left to the whims of politicians and their electoral prospects. He circled back to Ormsby-Gore with a question: How can we reengage the president and change his mind? At his ambassador’s suggestion, Macmillan wrote a thirteen-page letter that addressed all of Kennedy’s concerns in language he knew from Ormsby-Gore would resonate with the president. The prime minister appealed to his sense of duty as a leader, invoking the predictable Churchill references about finishing the work while time remained. The test ban treaty, Macmillan wrote, represented the “most important step” they could take as leaders.

The president and Ormsby-Gore met five days later to discuss the Macmillan letter. In this moment, would Kennedy emerge as a disciple of Baldwin or of Churchill? Would he do the right thing—what he knew needed to be done—no matter the political consequences? Ormsby-Gore homed in again on the essence of duty, emphasizing Macmillan’s deeply held belief that leaders were called to “change the course of history and guide it in a direction which would be of benefit to our peoples.” Kennedy wanted to be that sort of leader, but he couldn’t escape the hard political realities at play. If he advocated for a treaty and then lost the election to someone like Rockefeller, nuclear testing worldwide would continue indefinitely. However, as Ormsby-Gore pointed out flatly to his friend, that was the same morally weak argument Baldwin had used against rearming, when he told critics he might be replaced by the spineless Labour Party if he took such a route. Still, the conversation ended without a decision.

Then fate made a timely intervention. In the midst of Kennedy’s anguished deliberations, the United States granted Winston Churchill honorary citizenship. The president commemorated the occasion with a Rose Garden ceremony broadcast nationally as well as in Britain. Too frail to travel, Churchill sent his son Randolph, an old friend of Kick’s, to accept the honor. After downing a full bottle of Beefeater Gin, Randolph (whose drinking problem was well known) read out loud to the gathered dignitaries his father’s remarks, including his call for a robust British role in shaping the new Cold War world: “Let no man underrate our energies, our potentialities and our abiding power for good.” Kennedy listened with surging emotion. Hearing the words of Churchill’s son—whose preface to Arms and the Covenant had first laid out the Baldwin-Churchill divide twenty-five years earlier—finally convinced him that he had to do what was right. Kennedy pulled Ormsby-Gore aside later at the reception to tell him the treaty was back on.

Two days after the ceremony, the president called Macmillan to tell him that Averill Harriman was headed to the USSR as his personal emissary to secure a test ban agreement with Khrushchev. For the next two months, Kennedy would become the evangelist in chief, devoting significant political capital to selling the test ban to a skeptical public and Senate. Soon, his message that America must move from a “strategy of annihilation” to a “strategy of peace” started to gain traction with a public weary from years of nuclear brinkmanship.

In the midst of his test ban barnstorming, Kennedy took a detour to Germany to make a series of speeches. One of them became the famous “Ich bin ein Berliner” (“I am a Berliner”) address—widely regarded as the most audacious speech of Kennedy’s presidency and perhaps of the entire Cold War era—in which he personally identified with the city’s valiant struggle against communism. On his way to London afterward for an official visit with Macmillan, the president made two unscheduled, unannounced trips. First, he visited Shropshire, David Ormsby-Gore’s home county, spending just enough time to attend a church service and then to walk through the center of town. The visit was so low-key that it only became known in 2013. From there, he flew to the tiny town of Edensor where the president visited, finally, the grave of his sister Kick. Descending in a US Army helicopter, Kennedy made his way to the Devonshire family estate, Chatsworth, where in 1944 Billy Hartington had been laid to rest, followed four years later by his wife, Kick. Fifteen years earlier, Kennedy couldn’t overcome his grief to visit her grave. Now standing before it, her favorite brother prayed in the rain for several minutes before laying down a simple wreath. Ormsby-Gore and other family members stood by silently.

The president left London exultant over the success of his trip and looking forward to making further progress on the test ban treaty. As Harriman flew to Moscow to nail down a deal, Kennedy spent the weekend with his old friend in Hyannis Port, where Ormsby-Gore had first laid out his vision for disarmament nine years earlier. Now the two men were about to witness their grand dream become reality. With a pregnant Jackie taking notes, the two men talked, then talked some more. They golfed and monitored the deliberations in Moscow, then returned to Washington with guarded optimism.

Within ten days, Harriman had worked out a treaty that included a full ban on tests underwater, in the atmosphere, and in space (but not underground), with seven annual on-site inspections. Kennedy and Ormsby-Gore called Macmillan to relay the good news; he cried upon hearing it. The following day, the president made a national address announcing the pact, hailing it as the first step toward ending the Cold War. Two days later, with the Ormsby-Gores in tow, the Kennedys retired again to Hyannis Port to celebrate the monumental achievement.

As it turned out, it would take another twenty-five years before the Soviet Union would start to open up and a full thirty years before the Cold War would end. Still, there is no denying that the Limited Test Ban Treaty proved to be a historic milestone for peace in that long struggle.

The two friends had achieved much in the few short years of the Kennedy presidency. From safely navigating the Cuban Missile Crisis to securing the Limited Test Ban Treaty, they shifted the dangerous dynamic between the two superpowers to make the world a safer place. Thanks to the abiding trust and deep friendship shared by Jack Kennedy and David Ormsby-Gore—and their twenty-five-year conversation about leadership—the president of the United States did what was best for the country in the face of enormous political risk.

The morning of November 23, 1963, broke rainy and dreary in Washington, DC. David and Sissie Ormsby-Gore arrived at the White House, but instead of heading straight upstairs to the residence, as was their usual custom, they waited in a somber East Room with family and only a few other close friends for Jackie to come downstairs with her children.

They were there to offer prayers of thanksgiving for the life of Jack Kennedy, who the day before had been assassinated while riding through Dealey Plaza in Dallas. His flag-draped coffin sat on a bier in the middle of the room, surrounded by men representing the five branches of the military, rifles held at their sides. Shortly after ten o’clock, Jackie walked in with Caroline and John Jr. and a short mass commenced. Many people wept openly, and a few, like Ben Bradlee, were so overcome with emotion that they had to leave the room. “Jackie held up the longest,” Ormsby-Gore recalled. Afterward, the young widow walked around the room to say a word of comfort to every person there. When she got to David and Sissie, Jackie was so distraught she could barely speak. Still, in her whispered voice, she confided something they had never known in the three months since the Kennedys had lost their third child, Patrick, only days after his birth. Had the baby lived, she told them, Sissie would have been his godmother.

The death of Jack Kennedy affected Ormsby-Gore and Sissie profoundly. In its aftermath, Sissie would ruminate on the dinner she and David had at the White House a few nights before Jack and Jackie left for Dallas. “I told Jack he should have the roof up on the limousine when he drove through Dallas, but he said he couldn’t because he didn’t want people to think he was scared or hiding,” her eldest daughter, Jane, remembered her mother obsessing over afterward. For David, “the sun has gone down and Washington seems desolate and dull in comparison with the still so recent past,” he wrote to the recently resigned Macmillan, two months after the assassination.

A few months after vacating the White House for a home in Georgetown, Jackie sent Ormsby-Gore a reminder of his unique place in her late husband’s life: a book of poetry by Percy Bysshe Shelley, taken from JFK’s personal library and containing his presidential bookplate. Kennedy loved poetry—“What government corrupts, poetry cleanses,” he once declared—and Shelley was among his favorite poets. In a note accompanying the gift, Jackie wrote: “I wish I could give you the most precious thing that belonged to him—as precious as your friendship was to him—but nothing tangible could ever express that.”

The thrill of his post extinguished, Ormsby-Gore resigned as ambassador during President Lyndon Johnson’s second year in office. He returned to England, where he began a second career as a television executive, starting a Welsh television channel with the famed English actor Richard Burton that is still on the air today. In his absence, relations between the two countries suffered, losing “the finesse” that had marked the Kennedy/Macmillan/Ormsby-Gore years.

The people of Great Britain shared Ormsby-Gore’s grief. In May 1965, some five thousand people gathered at Runnymede to express their appreciation for what President Kennedy meant to their country. On the sacred ground where in 1215 King John signed the Magna Carta that led to England’s constitutional system of government, Queen Elizabeth II granted three acres to the US government on which to erect a memorial honoring the late president’s memory. It was an extraordinary and unprecedented gesture by the British government to a foreign leader. Accompanying the queen as she emerged to dedicate the memorial that day were Jackie and her two children, Jack’s remaining siblings, and David Ormsby-Gore.

David Ormsby-Gore would live another twenty years after that glorious afternoon. He became the fifth Lord Harlech upon the death of his father, inheriting the vast lands of the barony he knew so well from his wilderness years before entering Parliament. But heartbreak continued to stalk him. His wife, Sissie, with whom he had five children and a loving and happy marriage, would die in a car accident in June 1967—ironically, the same way he had lost his older brother in 1935. Jackie and Robert Kennedy flew to England to attend her funeral and burial.

After Sissie’s death, Jackie’s friendship with Ormsby-Gore deepened as they sought consolation in their mutual bereavement. Correspondence between the two, saved by Ormsby-Gore in two locked dispatch boxes only discovered in 2017, revealed that the friendship culminated in Ormsby-Gore asking Jackie to marry him. Gently deflecting the proposal in October 1967, Jackie wrote: “If I can ever find some healing and some comfort—it has to be with somebody who is not part of all my world of past and pain.… I can find that now—if the world will let us.” A year later, she stayed true to her word 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 of pain. In 1969, he married Pamela Colin, an American magazine editor.

But loss would never escape him. Over the next sixteen 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 sixty-six 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 ninety 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 “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.