Biographies & Memoirs

CHAPTER TWO

THE TWO JACKS

Adversity is the first path to truth.

—Lord Byron

The self-made rich man forever remains the poor kid he once was. The short boy, no matter how tall he grows, never stops measuring himself. Jack Kennedy, for all his apparent vitality as an adult, projected the shining image we remember mostly by an extraordinary force of will. We now understand that he was beset by lifelong pain in his stomach and back. What’s also clear, if you listen to those who knew him best, is that this deeper Jack, who spent so much time as the vulnerable youngster struggling toward sound health, endured over the decades.

It’s this bedridden child behind the man who transcended it all to become a war hero, congressman, senator, and president.

The burden of that effort gives us insight into John F. Kennedy. From an early age, there were two Jacks. He’d had to learn, from necessity, to separate his life into compartments, ones that eventually grew greater in number and more intricate in their interrelatedness as time passed and the number of his relationships increased.

At Choate he seemed to most of his classmates a sunny boy, full of good humor, always ready for fun. That was the picture he chose to present. But there were also, at school, the first signs of seriousness, and with it ambition. The young Jack revealed what would later be known as his “charisma,” and also, along with his risk-taking inclination, his leadership instincts and his innate political talent. When he reached Harvard in the fall of 1936, this Jack comes into sharper focus.

The standard take on Jack Kennedy is that he never intended a political career for himself until his brother’s death in World War II changed everything. But Jack was always ambitious. He was headed, one way or another, into public life. Even his father was starting to take notice of him as a leader, a kid exhibiting his own defiant spunk.

When summoned by the Choate headmaster, Joe Kennedy hadn’t quashed Jack’s Mucker spirit so much as honored it. You don’t get to be a tycoon, one of the richest men in the country, by saying “please” and “thank you” and sticking to the script.

Despite the fact that his dad had been a Harvard man, as was Joe Jr., Jack planned to spend his first year after Choate at the London School of Economics. While the LSE was known to favor a socialist point of view, Joseph Kennedy was a capitalist who liked being ahead of the market. He wanted his sons to have an edge on what he saw coming in the world.

But as fate would have it, Jack’s chronic stomach problems sent him reeling back to America after hardly more than a month there. Rather than return to London when he recovered, he chose to break a second time with Kennedy family tradition and, still shunning Harvard, entered Princeton. There were several good reasons for this decision, the main one being that his closest friend, Lem Billings, and another Choate pal, Rip Horton, were already there. It’s easy to see what such friendship meant to him, and how he was learning to have—to make, to keep—the kind of friends Lem and Rip represented.

Quickly moving in with them, he began attending classes. Then, once more, illness overtook him; standing six feet tall, Jack now weighed a puny 135 pounds. The blood-count roulette he was forced to play started up again, and, as his complexion went sallow, he resembled nothing so much as a scarecrow.

Back he went to Peter Bent Brigham Hospital in Boston for two months, and then, suffering also from asthma, he spent the remainder of the school year trying to recover under the dry desert sun of Arizona. Finally, facing the inevitable, he arrived in Cambridge that September to take his room in Weld Hall. He was a Harvard man.

Scrawny as he was, he quickly went out for freshman football. Whatever illnesses dogged him, he was doing his best not to let them define him. You couldn’t be the “sick kid” and still be popular the way he wanted to be. Interestingly, he followed his older brother’s lead in making a football star his best pal; three years ahead of him, Joe Jr. quickly had bonded with the quarterback, Timothy “Ted” Reardon. Jack’s new friend was Torbert Macdonald, his own class’s football hero, and Torby, like Lem before him, would come to know both Jacks. By sophomore year they were roommates.

One thing had changed. At Choate, he’d operated outside the system. Now at Harvard, his father’s and brother’s school, he seemed to be looking to succeed from within it. He ran for student office in both his freshman and sophomore years, falling short of success both times. Yet he continued to emphasize his quest for campus leadership over academic excellence.

“Exam today,” he wrote Lem at the end of his first semester, “so have to open my book & see what the fucking course is about.” But then he chalked up a social victory when he managed to get named chairman of the freshman “Smoker,” just as Joe earlier had been. Traditionally the class’s most elaborate party, the Smoker was considered a hot ticket, and expectations for it ran high.

Taking his responsibilities to heart, Jack didn’t disappoint, producing not one but two jazz bands for the occasion. “No matter who you were or what you did as a freshman . . . everybody went to the Smoker,” one of his classmates recalled. “It was a leadership activity at Harvard . . . a big deal. It was his first political success. So by this, Jack Kennedy had made his mark.”

Still, he had yet to outdo his brother. When he did, it would be a matter of beating Joe at his own game. During his sophomore year he was asked to join Spee, one of Harvard’s top final clubs. With that coveted invitation, the second son now possessed entrance into circles closed to both Joes. Demonstrating what we might call his “crossover appeal,” Jack, with his easy charm, had moved beyond the self-circumscribed orbit of the equally ambitious but unimaginative Joe Jr., who seemed unwilling to stride beyond the local Irish comfort zone. According to Joe’s tutor, John Kenneth Galbraith, the older brother was “slightly humorless, and . . . introduced all his thoughts with the words ‘Father says.’ “

Quickly becoming both well known and popular, Jack didn’t give off the impression that he was trying too hard, and he made good use of what his older brother never seemed to have, namely a light touch. And more than that, his conversation, friends said, ranged more widely than that of anyone else their age.

As Jack started to make a name for himself on campus, his energies at first were directed to such pursuits as arranging to meet Lem at the Stork Club in New York. Only in his “Gov,” or political science courses, in which he would eventually major, was the unexpectedly serious side to him glimpsed. Before an injury sidelined him—his congenital back troubles made worse by one leg’s being shorter than the other—Torby patiently threw passes for hours to help improve Jack’s skills as a receiver. Undaunted, Jack, who’d competed in backstroke at Choate, transferred his hopes for varsity success to the Harvard swim team.

Just as Lem would always be, Torby turned into a Kennedy constant, there when his friend needed support. Lem and Torby were the first recruits of what would one day grow to be an unofficial reserve corps of steadfast compadres always game for the next adventure. What Jack required from any of his new best sidekicks was one thing above all else, and that was rescue: from being alone, from being bored, from being stuck.

After spending Jack’s freshman year apart, in the summer of 1937 he and Lem crossed the Atlantic to embark on a traditional grand tour. Such an exciting trip was a way to try to erase the memories of Jack’s hospital stays that February and March. Sickness continued to be one specter he couldn’t charm his way past.

For two months they hit the road, having fun but also making sure they saw the best cathedrals and historic buildings. Jack showed himself willing to stay in the cheapest pensions to help keep down expenses for his friend. Being two high-spirited young Americans, they couldn’t help having a terrific time. It was nonetheless a moment when Europe’s dark political realities were visible even to the most fun-loving of tourists.

In France, where they stopped first, Jack wrote in his diary: “The general impression also seems to be that there will not be a war in the future and that France is much too well prepared for Germany.” Later, Lem would recall that his friend “was beginning to show more interest and more of a desire to think out the problems of the world. . . . He insisted, for instance, that we pick up every German hitchhiker. This worked out very well because a high percentage of them were students and could speak English. In that way, we learned a great deal about Germany.” Jack and Lem couldn’t resist making fun of the Nazis they saw: “Hi yah, Hitler!” they’d cheerfully call out.

The threat of war, in fact, was now less rumor than fact. The Third Reich had been rapidly rearming, and possessed an army and air corps that couldn’t help but cast a pall over Europe. When Hitler first showed his true colors and remilitarized the Rhineland, in total violation of the Treaty of Versailles, which had ended World War I, neither Britain nor France rose up to challenge him. Thoughts of war, to most Europeans, too vividly brought back the devastation wrought by World War I, when masses of young soldiers were thrown against one another in a conflict that left the continent in carnage.

Returning to Cambridge for his sophomore year, Jack soon faced an array of familiar, disturbing physical setbacks. As always, he fought against them in his own way. To remain on the swim team—as freshmen, they’d gained glory by being undefeated—was one of his goals. Thus, when he found himself in Stillman Infirmary, he relied on Torby, who brought him steaks and ice cream to tempt his appetite and build up his strength. His friend even snuck Jack out to the indoor swimming pool to get the practice time he needed. Swimming for Harvard was serious business, after all, and team members were expected to sandwich in four hours a day between classes.

Then, just before the year drew to a close, Franklin Roosevelt, now in the first year of his second White House term, threw a joker into the U.S. international diplomacy game: he named Joseph P. Kennedy, Sr., ambassador to Great Britain. It’s impossible to figure out exactly what mix of motives inspired this maladroit appointment. Certainly domestic politics played a major role, for Irish-American voters made up a huge faction of the Democratic constituency. Also, given his background and connections, Joe Kennedy’s presence in London might help resolve the tricky situation between Ireland and Britain. However, if Roosevelt imagined that his new envoy would act as his surrogate in trying to stiffen the spine of the British when it came to facing down Nazi aggression, he was, sadly, wrong.

The choice of Kennedy, who’d been an early, generous FDR supporter, for this ultimate plum offered the wily Roosevelt the satisfaction of making him into a retainer—a well-rewarded one, but a retainer nevertheless. Both men were well aware the job had to be entrusted to someone able to foot the extravagant costs its social traditions demanded. Ever the bold striver, Joe wanted badly to go there and was ready to spend whatever it took. Until the consequences of sending him to London would prove too large, FDR, too, was ready to weather them.

With his credentials ready to present at the Court of St. James, Joe arrived in London in early 1938, just eleven days before Hitler demanded acceptance of Anschluss—in effect, annexation—from the government of his native Austria. Such a relationship between the two countries had been forbidden by the allies at the end of World War I, but the Führer ignored it. Bent on expanding the borders of the great German-speaking state he envisioned, he signaled ever louder his disdain for those who considered themselves Germany’s masters.

The Treaty of Versailles for him was no longer worth the paper it had been written on, and so the next territory he looked to grab was the German-speaking part of Czechoslovakia, the Sudetenland, taken from Germany by the allies in 1919.

He had only a simple goal, Hitler told the world—acting the perfect wolf in sheep’s clothing—and that was to see all Germans united into one country. Hearing this, Germany’s old European and British antagonists managed, hiding their faces in the sand, to justify tolerating it as a means to preventing the continent from again morphing into a bloody battlefield. Meanwhile, to the newly arrived American ambassador to Great Britain, a new war was out of the question. In late September 1938, British, French, and Italian diplomats fatefully met in Munich and there gave in to Hitler’s demands for the Sudetenland. The British delegation was led by Prime Minister Neville Chamberlain, whose reputation would ultimately be destroyed by this concession to the Germans.

Returning to Britain, he announced, “We regard the agreement signed last night and the Anglo-German Naval Agreement as symbolic of the desire of our two peoples never to go to war with one another again.” Later that day, he stood outside 10 Downing Street and this time said, “My good friends, this is the second time in our history that there has come back from Germany to Downing Street peace with honour. I believe it is peace for our time.”

Events would swiftly prove him wrong.

Ambassador Kennedy, as soon as he’d arrived in London, formed a close relationship with Chamberlain, and it wasn’t long before they were in almost daily contact. After the Munich capitulation, Joe made widely known his approval, and gave in October a Trafalgar Day speech that spoke of the need for “democratic and dictator countries” to focus on their similarities and not their differences. “After all, we have to live together in the same world, whether we like it or not,” he declared. It could hardly have been worse timing. Only three weeks later came Kristallnacht, or Night of Broken Glass, when across Germany and Austria state-sanctioned violence against Jews and Jewish property raged for two days, shocking the world.

Repugnant as appeasement strikes us today, Joe Kennedy wasn’t that out of sync with the prevailing temper of the British Establishment. Events were moving swiftly to force the democracies to make a stand, but the reluctance of the ruling class to engage with the Third Reich died hard. Four years earlier the Oxford Union, the legendary university debating society, after hearing arguments pro and con, had notoriously resolved not to fight “for King and Country,” and that remained still a popular, if increasingly indefensible, position in London’s drawing rooms.

Only the politician and ardent historian Winston Churchill—who was a hero, through his writings, to Jack Kennedy—had steadily been speaking out, from his backbench in Parliament, against the pacifist temper of the times. And people were beginning to listen to him.

It’s very hard, looking at this now, to accept that Jack’s father never seemed to feel any shame about backing appeasement. Joe’s detachment from the sentiments of the times had always been his strength in business, as he invested or divested against the popular current. However, after Kristallnacht, when it was starkly evident that there could be no accommodation with Nazism, Ambassador Kennedy was out there on his own.

For a twenty-one-year-old American, the thought of war carried personal meaning. It brought with it both excitement and dread. Young men of Jack Kennedy’s age had died by the hundreds of thousands in the century’s first great European war. Now the daily press clamored the drumbeat of a second. Young Jack Kennedy was about to enter the very theater in which the question would be decided: Would Britain stand another Nazi demand for territory?

He had come to visit his family that summer of 1938, joining them on vacation in the South of France. It was decided that he’d figure out a way to spend the coming spring semester of his junior year working as his father’s secretary in London; it meant he’d have to get permission to double up his classes at school in the fall term, but this was an opportunity to witness history.

Jack knew the valor Britain had shown in the Great War. He was powerfully affected by Winston Churchill’s description of the willing courage of an upper-class Englishman, Raymond Asquith. Son of Herbert Asquith, the Liberal prime minister under whose leadership the British entered the Great War, Raymond was four years younger than Churchill and a much-admired, much-loved role model for his generation. His brave death on a French battlefield stood for all that was fine, and the tribute Churchill had written to him struck for Jack a resonant chord: “The War which found the measure of so many never got to the bottom of him, and when the Grenadiers strode into the crash and thunder of the Somme, he went to his fate cool, poised, resolute, matter-of-fact, debonair.” In later years he would quote this passage from memory.

However, the poignancy of young death for a noble cause seemed far removed from the moral climate Jack began to sense around him as he spent more time in England beginning in February 1939, when he took up his post at the embassy. Arriving primed to enjoy the perks of the ambassador’s family, he found himself distracted not just by the predictable flood of society invitations but also by the debate being waged.

By March, it was clear Hitler was looking to take more land beyond the chunk of Czechoslovakia ceded to him at Munich. All at once, with no warning, Hitler fulfilled the watching world’s worst fears and defiantly laid claim to all of Czechoslovakia. Immediately, the issue turned to neighboring Poland’s sovereignty. Would the British take their stand now?

Despite the increasingly alarmed warnings of Winston Churchill, the Chamberlain government had been hugging the belief that a second major war could be avoided. It knew that neither the British public’s memory of the human devastation of the trenches of WWI nor the traumas of the returning survivors had lessened; a generation had been lost, with the country, overall, remaining shell-shocked.

For the first time in his life—as he learned the ways of a country not his own but mattering greatly to him—Jack Kennedy found himself seeing men and women wrestling with national principles. Quickly pegged as a highly desirable bachelor and invited everywhere, he grew increasingly sensitive to the atmosphere around him—and soon began to feel the disharmony unbalancing it.

On the one hand, his father continued to support Chamberlain, in direct opposition to the position fiercely held by Churchill. Churchill’s assessments of German capabilities, Jack was aware, had proved—and continued to prove—startlingly accurate. He couldn’t help but respect Churchill’s arguments, despite knowing that his own father and the ruling-class parents of his new friends openly dismissed the former cabinet minister as a warmonger. And while Jack was intellectually open, he was still a son with a powerful father.

Jack was also convinced, as he grew to be at home in the continual round of parties and pleasures, that something vital was missing in the character of those privileged young English whose company he was so enjoying. Charming they were, and always delightful hosts, yet he found himself doubting the current state of their mettle—their fighting spirit. Even in front of them he didn’t hesitate to share his observation that the once-valiant English elite seemed to have turned “decadent” over the two decades since the last war. How could they ever rally themselves and prevail against such a threat as the Third Reich?

In short, they were no Raymond Asquiths.

Mulling over what he was hearing and seeing, he began to form for himself a notion of where Britain’s elected leaders had failed. He began to work out his ideas on the subject of leadership, the ones he would continue to consider for the rest of his life.

When the Nazis invaded Poland on September 1, 1939, Jack was still in Europe, having been touring again that summer, this time with Torby. Three days later, he sat with his parents and sister Kathleen in the Strangers’ Gallery of the House of Commons and witnessed Prime Minister Chamberlain declare war against Germany. Returning to college at the end of September, by which time the Luftwaffe had begun dropping its bombs, he seemed a different person.

Certainly, in the opinion of Torby—who was there—his friend “had definitely changed. I don’t think he really got interested in the intellectual side of academic life until perhaps his junior year when war seemed to bring a lot of us, especially Jack, a recognition that it wasn’t all fun and games and that life was about to get very real and earnest.”

But what was happening to Jack continued as an evolution. Then, in early June of 1940, he took a visible stand, writing a signed letter to the Harvard Crimson, implicitly renouncing his father’s position. Even in 1940, once the war was under way, Joe had hoped the British would soon find a way to make peace with Hitler. He spoke disparagingly of Britain’s and France’s prospects, in a letter to Roosevelt, giving them hardly “a Chinaman’s chance” of prevailing.

In his letter to the Crimson, Jack noted sharply: “The failure to build up her armaments has not saved England from a war, and may cost her one. Are we in America to let that lesson go unlearned?”

He’d chosen this for his Harvard senior thesis. “Appeasement in Munich” was its title, and it shows how Jack’s thinking was diverging from that of his father. Reading it today, what you recognize is that it’s actually a masterful political compromise, reconciling the views of his dad with the growing American consensus. Soon to be retitled Why England Slept and commercially published that same year, what Jack’s analysis argues, to begin with, is that Britain simply had been unprepared in 1938. Had the British gone to war then, they would have lost badly. Most crucially, their defense capability was short the trained fighter pilots needed to keep at bay the Luftwaffe, the fearsome German air force.

The two years between 1938 and 1940, then, were critical, he contends, because, had the war begun at the earlier date, Britain would have been naked to its enemies. The beauty of this argument is that it mitigates the moral failure of giving away a country and its people to Adolf Hitler. Joe Kennedy, one assumes, wouldn’t have forsworn appeasement based simply on a shift in the balance of weaponry. He didn’t believe in fighting Hitler under any circumstances. But, while Jack makes the case that Chamberlain had no choice but to parlay and retreat, the real issue now, for him, is that the United States, his own country, must take the lesson and do better.

“I do not believe necessarily,” he wrote, “that if Hitler wins the present war he will continue on his course to world domination. . . . But, in the light of what has happened in the last five years, we cannot depend on it.”

In other words, America needed to get its act together and stop blaming Chamberlain, and therefore his own father, for not doing what it still needed to do. It was a masterful exercise in intergenerational politics. Here was the son, taking on, without condemning, the father’s indefensible position on what would soon be revealed as the worst horror of the century. He was doing so with such a deft touch that his father took no apparent offense. In truth, he was saying that Britain should have been morally prepared to fight, and his father was saying Britain should still avoid the fight.

What Jack now proposed was that America be prepared to fight, not repeating Britain’s error. “England made many mistakes; she is paying heavily for them now. In studying the reasons why England slept, let us try to profit by them and save ourselves her anguish.” Why England Slept quickly became a best seller on both sides of the Atlantic, and Jack donated the royalties from the British edition to the fund to rebuild war-scarred Plymouth.

It is yet another manifestation of the two Jacks: the young American drawn to Churchill’s mind and fearlessness on the one hand, and the son whose father was equally fearless but to a different purpose. To reconcile the lessons of these two figures was a task for which he had needed to make the effort.

Again, it was masterful politics. If Joe Kennedy had been paying strict attention, he would have spotted the end run his son was making around him here. Jack was arguing that Britain didn’t fight because it hadn’t rearmed. But wasn’t that tantamount to saying Britain should have been ready to fight? And wasn’t that a subversion of his father’s own position? Jack had done more than find a middle ground with his father; he’d subtly taken that ground right out from under him.

That fall, the senior Kennedy would be forced from his job in London, a victim of his poor judgment. He had been quoted in a Boston Globe column saying, “Democracy is finished in England. It may be here.” Jack’s career would go on to be a continual balancing act between the nobility of valiant death on the battlefield, so admired by Churchill, and the horror of war itself, so understood by Chamberlain and backed by the hardnosed Joe Kennedy.

Jack felt deeply the emotional weight of the valor, commitment, and sacrifice demanded by war. Nothing makes this clearer than his beloved Pilgrim’s Way, the autobiography of John Buchan, famous for writing The Thirty-Nine Steps. Published in 1940, it immediately became a favorite and would remain the best-loved book of his life. Most significant, in its pages he again encountered the widely mourned figure of Raymond Asquith, about whom Churchill had written so movingly.

“He loved his youth,” Buchan wrote of Asquith. “And his youth has become eternal. Debonair and brilliant and brave, he is now part of that immortal England which knows not age or weariness or defeat.”

Jack loved courage, hated war. That conflict would define his view of history’s leaders. As we will see very soon, it will define how he viewed himself.

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