October 14th, 1962. A U-2 spy plane snaps photos that change everything: Soviet missiles in Cuba, capable of reaching most of the United States within five minutes.
For the next 13 days, every decision could end human civilization or save it.
Here's what should terrify you: if Kennedy had used the same decision-making process that led to the Bay of Pigs disaster, you wouldn't be reading this. We'd all be radioactive dust.
Instead, he did something today's leaders would consider weakness: he deliberately made himself vulnerable to disagreement.
When Your General Calls You Neville Chamberlain
Picture this: Air Force Chief of Staff Curtis LeMay pounds the table, demands immediate airstrikes on Cuba, then looks Kennedy in the eye and compares him to Neville Chamberlain—the appeaser whose weakness led to World War II.
In most administrations, calling the President a coward is career suicide.
Kennedy didn't fire LeMay. He didn't shut down the discussion. He thanked him for the assessment.
Because after Bay of Pigs, Kennedy had learned something that saved the world: when everyone agrees with you, that's when you should be most terrified.
The Process That Prevented Armageddon
Kennedy's Cuban Missile Crisis approach was revolutionary:
He assigned advisors to argue different positions—whether they believed them or not. Their job was finding flaws, not agreement.
He left the room during crucial discussions. The moment Kennedy stepped out, advisors who'd been reluctant to express doubts became brutally honest about military action's risks.
He encouraged his own brother to change his mind. Attorney General Robert Kennedy initially said "I think we should take Cuba back." After days of deliberation: "Any action we take against Cuba will lead to nuclear war."
If they'd gone with their first instinct—attack—we'd likely have had nuclear war.
The Solution Nobody Saw Coming
Through brutal intellectual combat, they found a third option: naval "quarantine" plus diplomatic pressure. Not the military's preferred invasion. Not the doves' "do nothing." Something entirely new that emerged only through systematic disagreement.
Behind the scenes, Robert Kennedy conducted secret negotiations. The final deal: Soviets remove missiles in exchange for a public US pledge not to invade Cuba and secret removal of American missiles from Turkey.
October 28th: Khrushchev announced withdrawal. Nuclear war avoided.
This wasn't luck—it was process.
The "Soft Underbelly" Strategy
Kennedy understood something today's leaders don't: strong leadership requires making yourself vulnerable to disagreement.
You need a "hard shell" of core values to handle having a "soft underbelly" that advisors can poke and prod. Kennedy could withstand being called Neville Chamberlain because he knew who he was and what he stood for.
Today's leaders have it backwards. Hard shells against disagreement, soft underbellies on values. They can't tolerate challenge because they're not sure what they believe.
The Contrast with Today
Fast-forward to 2025: The FBI uses polygraph tests to identify employees who said something negative about leadership. Not spies. Dissenters.
Forty percent of FBI field offices have lost top agents—purged for conducting legitimate investigations political leadership didn't like.
Cabinet meetings are North Korean-style tribute sessions. Press corps filled with loyalists asking softball questions.
This is the exact Bay of Pigs dynamic, but on purpose. We know better. We have Kennedy's example. We understand the consequences. And we're choosing groupthink anyway.
When Reality Becomes Optional
We're implementing tariff policies that contradict economic research. Removing vaccine preservatives based on perception, not science. Investigating "weather manipulation" everyone knows doesn't exist.
When a reporter questioned the press secretary's economics understanding, she responded: "How dare you question my understanding?"
But questioning is literally the job. If you can't handle scrutiny, you don't belong in leadership.
The Architecture of Disaster
Kennedy learned hard lessons in Cuba's swamps, paid with 1,400 lives, then used that knowledge to prevent nuclear war.
We're learning nothing.
We're systematically recreating disaster conditions:
Purging competent advisors who might disagree
Elevating loyalty over truth
Treating dissent as betrayal
Creating echo chambers where bad ideas go unchallenged
Kennedy's job wasn't being liked—it was making good decisions. Good decisions require honest advisors willing to tell uncomfortable truths.
What You Can Do
In meetings: Ask "What could go wrong?" when everyone's nodding. Be the devil's advocate.
As a manager: Create processes encouraging disagreement. Assign people to argue against your preferred option. Leave the room so people can speak freely.
As a citizen: Demand leaders who surround themselves with people smarter than they are. Be suspicious of politicians hiring only loyalists.
Most importantly: Being right matters less than getting it right. Changing your mind isn't weakness—it's wisdom.
The Stakes
Kennedy's transformation created architecture that worked for decades. We're dismantling it deliberately.
When you silence dissent, you don't eliminate bad news—you ensure you won't hear it until it's too late. When you demand loyalty over competence, you get yes-men while the world burns.
The question isn't whether catastrophic failures will come. It's whether we'll learn in time.
Because in our interconnected world, the next disaster might not offer the luxury of learning from mistakes.
Remember: When everyone agrees with you, you should be most afraid of what you're not hearing.
Where do you see groupthink in your world? How do you encourage productive dissent? Hit reply—I read every response.
Based on our latest Masters of Influence podcast episode about how 13 days of systematic disagreement saved civilization.
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