Leadership lessons from the Cuban Missile Crisis

As the world stared down the barrel of nuclear war, JFK was a model of calmness, says author Ryan Holiday.

by Ryan Holiday
Last Updated: 10 Oct 2019
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The entire world changed in the few short hours between when John F. Kennedy went to bed on October 15, 1962, and when he woke up the following morning. While the president slept, the CIA identified the ongoing construction of medium- and long-range Soviet ballistic nuclear missile sites on the island of Cuba, just 90 miles from American shores. 

As Kennedy received his first briefing on what we now know as the Cuban Missile Crisis, he could consider only the appalling stakes. As many as 70 million people were expected to die in the first strikes between the United States and Russia. But that was just a guess — no one actually knew how terrible nuclear war would be.

Whatever factors had contributed to its creation, no matter how inevitable war must have appeared, it fell on the president, at the very least, to just not make things worse, because it might mean the end of life on Earth. 

With almost no executive leadership experience under his belt, it’s not a surprise that the first year and half of Kennedy’s administration had not gone well. 

In April 1961, Kennedy had tried and failed — embarrassingly so — to invade Cuba and overthrow Fidel Castro at the Bay of Pigs. Just a few months later, he was diplomatically dominated by Soviet premier Nikita Khrushchev in a series of meetings in Vienna. (Kennedy would call it the "roughest thing in my life.") 

Sensing his adversary’s political weakness, Khrushchev repeatedly lied to Kennedy about any weapons being placed in Cuba, insisting that they would be for defensive purposes only. Which is to say that during the Missile Crisis, Kennedy faced, as every leader will at some point in their tenure, a difficult test amid complicating personal and political circumstances. 

The advice from Kennedy’s advisors was immediate and emphatic: The missile sites must be destroyed with the full might of the country’s military arsenal. Every second wasted risked the safety and the reputation of the United States. After the surprise attack on the missiles, a full-scale invasion of Cuba by American troops would need to follow. This, they said, was not only more than justified by the actions of the USSR and Cuba, but it was Kennedy’s only option. 

Their logic was both primal and satisfying: aggression must be met with aggression. Tit replied to with tat. The only problem was that if their logic turned out to be wrong, no one would be around to account for their mistake, because everyone would be dead. 

Unlike in the early days of his presidency, when Kennedy allowed the CIA to pressure him into supporting the Bay of Pigs fiasco, this time he surprised everyone by pushing back. Kennedy wanted everyone to slow down so that they could really think about the problem in front of them. This is, in fact, the first obligation of a leader and a decision maker. Our job is not to "go with our gut" or fixate on the first impression we form about an issue. 

No, we need to be strong enough to resist thinking that is too neat, too plausible, and therefore almost always wrong, because if the leader can’t take the time to develop a clear sense of the bigger picture, who will? 

Show empathy

We can see in Kennedy’s handwritten notes taken during the crisis, a sort of meditative process by which he tried to do precisely this. On numerous pages, he writes "Missile. Missile. Missile," or "Veto. Veto. Veto. Veto," or "Leaders. Leaders. Leaders." On one page, showing his desire to not act alone or selfishly: "Consensus. Consensus. Consensus. Consensus. Consensus. Consensus." 

On a yellow legal pad during one meeting, Kennedy drew two sailboats, calming himself with thoughts of the ocean he loved so much. Finally, on White House stationery, as if to clarify to himself the only thing that mattered, he wrote one short sentence: "We are demanding withdrawal of the missiles." 

Perhaps it was there, as Kennedy sat with his advisors and doodled, that he remembered a passage from another book he’d read, by the strategist B. H. Liddell Hart, on nuclear strategy. In Kennedy’s review of Hart’s book for the Saturday Review of Literature a few years before, he quoted this passage: 

"Keep strong, if possible. In any case, keep cool. Have unlimited patience. Never corner an opponent, and always assist him to save face. Put yourself in his shoes — so as to see things through his eyes. Avoid self-righteousness like the devil — nothing is so self-blinding."

It became Kennedy’s motto during the Missile Crisis. "I think we ought to think of why the Russians did this," he told his advisors. What is the advantage they are trying to get? he asked, with real interest. "Must be some major reason for the Soviets to set this up." 

As Arthur Schlesinger Jr., Kennedy’s advisor and biographer, wrote, "With his capacity to understand the problems of others, the President could see how threatening the world might have looked to the Kremlin." 

This understanding would help him respond properly to this unexpected and dangerous provocation — and give him insight into how the Soviets would react to that response. It became clear to Kennedy that Khrushchev put the missiles in Cuba because he believed Kennedy was weak. But that didn’t mean the Russians believed their own position was particularly strong. Only a desperate nation would take such a risk, Kennedy realised. 

Armed with this insight, which came through long discussions with his team, he began to formulate an action plan. Clearly, a military strike was the most irrevocable of all the options (nor, according to his advisors, was it likely to be 100 percent effective). 

What would happen after that, Kennedy wondered? How many soldiers would die in an invasion? How would the world respond to a larger country invading a smaller one, even if it was to deter a nuclear threat? What would the Russians do to save face or protect their soldiers on the island? 

These questions pointed Kennedy toward a blockade of Cuba. Nearly half of his advisors opposed this less aggressive move, but he favoured it precisely because it preserved his options. The blockade also embodied the wisdom of one of Kennedy’s favorite expressions: It used time as a tool. It gave both sides a chance to examine the stakes of the crisis and offered Khrushchev the opportunity to reevaluate his impression of Kennedy’s supposed weakness. 

Stillness is a virtue

What’s most remarkable about this conclusion is how calmly Kennedy came to it. Despite the enormous stress of the situation, we can hear in tapes and see in transcripts and photos taken at the time just how collaborative and open everyone was. 

No fighting, no raised voices. No finger-pointing (and when things did get tense, Kennedy laughed it off). Kennedy didn’t let his own ego dominate the discussions, nor did he allow anyone else’s to. When he sensed that his presence was stifling his advisors’ ability to speak honestly, he left the room so they could debate and brainstorm freely. 

Reaching across party lines and past rivalries, he consulted openly with the three still-living ex-presidents and invited the previous secretary of state, Dean Acheson, into the top-secret meetings as an equal. 

In the tensest moments, Kennedy sought solitude in the White House Rose Garden (afterward, he would thank the gardener for her important contributions during the crisis). He would go for long swims, both to clear his mind and to think. He sat in his specially made rocking chair in the Oval Office, bathed in the light of those enormous windows, easing the pain in his back so that it might not add to the fog of (cold) war that had descended so thickly over Washington and Moscow. 

There is a picture of Kennedy with his back to the room, hunched over, leaning both fists on the big desk he had been chosen by millions of voters to occupy. This is a man with the fate of the world on his shoulders. He has been provoked by a nuclear superpower in a surprise act of bad faith. Critics are questioning his courage. There are political considerations, personal considerations, there are more factors than any one person should be able to weigh at one time. 

Yet he lets none of this rush him. None of it will cloud his judgment or deter him from doing the right thing. He is the stillest guy in the room. 

The space Kennedy gave Khrushchev to breathe and think paid off just in time. On October 26, eleven days into the crisis, the Soviet premier wrote Kennedy a letter saying that he now saw that the two of them were pulling on a rope with a knot in the middle — a knot of war. The harder each pulled, the less likely it would be that they could ever untie it, and eventually there would be no choice but to cut the rope with a sword. 

Suddenly, the crisis was over as quickly as it began. The Russians, realising that their position was untenable and that their test of US resolve had failed, made signs that they would negotiate — that they would remove the missiles. The ships stopped dead in the water. 

Kennedy was ready too. He pledged that the United States would not invade Cuba, giving the Russians and their allies a win. In secret, he also let the Russians know that he was willing to remove American missiles in Turkey, but would do so in several months’ time so as not to give the impression that he could be pressured into abandoning an ally. 

With clear thinking, wisdom, patience, and a keen eye for the root of a complex, provocative conflict, Kennedy had saved the world from a nuclear holocaust. 

Extract published with permission from Stillness is the Key: An Ancient Strategy for Modern Life by Ryan Holiday, published by Profile Books 10th October 2019, RRP£12.99.

Image credit: Paul Schutzer/The LIFE Picture Collection via Getty Images

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