The Stupid Cuban Missile Crisis
Donald Trump is unfit for office. He might do genocide before Congress recognizes that.
When President John F. Kennedy discovered the Soviet plan to put nuclear missiles on Cuba, he wasn’t thrilled.
Soviet Premier Nikita Khrushchev had worked pretty hard to keep this operation clandestine. The USSR had been dispatching waves of cargo ships, laden with civilian-clothed soldiers, equipment, missiles, and nuclear warheads. They sailed from Europe to Cuba, unloading their secret cargo and transporting them hundreds of kilometers through the Caribbean jungles. They faked car accidents and dispatched empty cargo trucks across the island to obfuscate their enormous mission. Soviet soldiers spoke only in memorized Spanish, lest American spies were skulking about.
In the span of just weeks, the Soviets built a network of missile silos and launchpads capable of raining nuclear weapons on the continental United States.
The United States was caught off-guard. Kennedy had previously suspended the CIA-run U-2 spy program after its discovery irked the Soviets and Chinese alike. Without that eye in the sky, he discovered those missile silos too late.
An irate White House declared this build-up would be prevented “by whatever means may be necessary.” He was too late. Kennedy didn’t know it, but nuclear warheads were already en route to Cuba.
“The main goal of the American statement was to warn Khrushchev about crossing a red line,” historian Serhii Plokhy writes. “His reaction was just the opposite — to cross it as soon as possible.”1
The two men thought they had an understanding of each other. Khrushchev didn’t want to weaken Kennedy’s position ahead of the midterms, and Kennedy didn’t want to incentivize further Soviet action in divided Berlin.
“He can’t do this to me,” Kennedy ranted to his advisors. Their relationship was supposed to be defined by calculated moves and a level of political symbiosis.
“The question,” one of Kennedy’s officials told him, is not whether the base is removed from Cuba, but “whether we do that by a sudden, unannounced strike of some sort, or we build up the crisis to the point where the other side has to consider very seriously about giving in.” To prepare for the former option, Kennedy sought Congressional approval to call up 150,000 soldiers for a possible invasion of Cuba.
Khrushchev, meanwhile, believed he had to project strength or risk subjugation. “It’s been a long time since you could spank us like a little boy,” Khrushchev had declared some months earlier, “now we can swat your ass.”
Both men were too effective in their statecraft. Kennedy thought Khrushchev was trying to distract the world while it constructed the Berlin wall. In fact, Khrushchev hoped that Berlin would be a “diversionary maneuver” to distract from their build-up in Cuba. Both men were getting lost in their own tit-for-tat.
“It’s just as if we suddenly began to put a major number of [medium-range ballistic missiles] in Turkey,” Kennedy seethed. “Now that’d be goddam dangerous, I would think.” An official noted that America had put ballistic missiles in Turkey. Kennedy shrugged it off. “Yeah, but it was five years ago.”
Kennedy’s advisors wanted to invade. The president’s brother even suggested staging a false flag to justify such a war. Khrushchev — and Cuban dictator Fidel Castro — believed invasion was imminent.
It was Secretary of Defense Robert McNamara who suggested the idea of a naval blockade to halt further shipments. Khrushchev was thrilled with that plan. “We’ve saved Cuba,” he declared. “The point is that we do not want to unleash a war,” the Premier told his advisors. “We want to intimidate and restrain the USA vis-à-vis Cuba.”
In the spirit of de-escalation, Khrushchev declined to put the Cuban missiles on alert. Kennedy, worried about looking weak, moved the U.S. DEFCON 2. (When he heard of this news, per one Soviet official, Khrushchev “shat his pants.”)
Those 13 days in October, 1962 marked arguably the closest humanity has come to nuclear annihilation. It wound up there thanks to a series of bluffs and overreactions, prevarications and responses, political maneuvers and unforeseeable mishaps.
But those two weeks were also marked by two leaders — craven and unpredictable as they may have been — doing the right thing.
Consider October 23, when an irritable and sleep-deprived Khrushchev stalked through the Kremlin: Screaming, cursing, and threatening to nuke the White House. And then, he decided to take his senior officials to the opera.
“Comrades, let’s go to the Bolshoi Theater,” Khrushchev said. “The atmosphere in the world is tense now, but we’ll make an appearance in the theater. Our people and foreigners will see it, and that will begin to have a calming effect.”
Whether it mattered to Kennedy is unclear. But it certainly calmed his comrades.
This effort to restrain hostilities went right through both militaries.
Amid a days-long hunt for Soviet submarines in the Bermuda Triangle, the crew of the USS Cony finally sighted a sub surfacing, its crew waving the red flag. The American destroyer monitored the Soviet sub in a strange, yet managed, stand-off. Then, an anti-submarine Neptune aircraft swooped low, dropping incendiary devices to light its massive photoelectric camera. The Soviet sub crew were so alarmed that they readied their torpedo tubes, thinking the stand-off was about to turn hot. Had they fired, it would have sent a nuclear-tipped missile directly into the hull of the USS Cony.
The U.S. Navy crew — using their deck spotlights to convey messages via the Cyrillic Transliteration Table, the International Signals Book, and Morse Code — didn’t just plead with the Soviets for calm. They apologized. The Soviets closed their torpedo doors. The American commander nodded to recognize his Soviet counterpart, the Soviet nodded back.
The possibility of peace and de-escalation was constantly undermined by public bravado. But that, in turn, was lessened by frequent backchanneling sent via telegram and interlocutors. Both men understood well the possibility that the other side could miscalculate — because each man had miscalculated throughout their dealings with the other.
“Ours is a joint account,” Khrushchev noted at one point, “and each of us must see that there is no miscalculation.” A funny line for a communist.
This great power competition, we know, ended without war.
But it was not, as some quack historians would tell you, a simple test of strength. It was, instead, a series of gambles, bluffs, climb-downs, and compromises. It was two leaders ultimately acting with logic and compassion, at least when it counted the most.
I’ve been thinking about those 13 days in 1962 a lot, recently, while watching President Donald Trump pursue his fundamentally dumb war in Iran. It’s his Stupid Cuban Missile Crisis.
The stakes may be lower than they were 60 years ago. But the quality of strategic thought on offer is even lower.
Trump, the man chiefly responsible for this boondoggle, has the kind of intelligence, indicators, analysis, proposals, insight, and operational flexibility that Kennedy could only dream of. He has an opponent who is willing to negotiate. He has overwhelming military superiority and the support of all regional players. And yet, unlike JFK, Trump has consistently pursued the stupidest imaginable path.
Since his first stint in office, Trump’s strategic incoherence — brought on by his own arrogance, the messianic boobs who surround him, and his refusal to listen to his career civil servants — has worked out surprisingly well. Through mafioso tactics and sheer luck, he has covered the downside while eking out strange and unexpected upsides.
It was never going to last. And Trump’s luck has finally run out in Iran.
This leaves the president in an impossible bind. Shown for the weak, reckless fraud that he truly is, Trump must find some way to save face and project strength. We should desperately hope that someone can stop him before he does.
I sat in my office earlier this month, flipping back-and-forth between Iranian and American propaganda channels, waiting to see if the genocide was about to begin.
As I began tapping out the first draft of this dispatch, I started counting the ways in which the world had tried — quite successfully — to prevent such a war. And also the myriad ways in which its main belligerents were determined to make it happen.
Iran had become a revolutionary theocracy in 1979. But its extremism didn’t reach the levels of nuclear weapons until 19872 — after seven years of a brutal and genocidal war launched on it by Saddam Hussein. The Iraqi dictator had no real objective nor much of a plan. Saddam invaded Iran simply to beat a rival. Faced with the fanaticism of Iranian fighters, who died in enormous numbers, he resorted to desperate tactics. Iraq gassed Iranian villages and attacked Iran-bound ships in the Strait of Hormuz. That didn’t work either, and the world eventually intervened to end the fighting.
Tehran — which had just won a war by sending waves of barely-armed soldiers into enemy fire and then by innovating military solutions — adopted fanaticism as a foreign policy. And there is nothing more fanatical than building a nuclear bomb.3
The existence of such a weapons program remained mostly secret until details of the missile silos were revealed in a series of disclosures starting in 2003. President George W. Bush was already fighting two land wars in the Middle East and he was threatening to do a third in Iran. So Tehran suspended the program in 2004 — and it hasn’t restarted it since.45
What Iran did do was to pursue a uranium enrichment program. That uranium, if enriched to about 90% purity, could fill a warhead for a nuclear missile. And Iran could reboot that weapon program and create such a missile in fairly short order. And as tensions in the Middle East worsen, particularly with the return of Benjamin Netanyahu, Iran started to up its enrichment. By the early 2010s, it hit 20% purity. Analysts feared that Iran, if it kept enriching and suddenly rebooted its nuclear weapons program, was about a year away from hitting that 90% level and building a rocket to deliver the nuclear payload.
And this atomic threat worked. The United States and Europe rushed together and started negotiating a deal with Iran. The ensuing agreement, the JCPOA, meant an end to sanctions against Iran, recognition of Iran’s peaceful nuclear program, and the unfreezing of some much-needed Iranian assets. It also provided for a dispute-resolution process: A venue at which Tehran could exchange rule-breaking for a face-to-face meeting to air its grievances. But Iran stuck to the deal, and kept its nuclear program humming at a 3.67% enrichment level.
The nuclear program simply became less important. President Barack Obama backed away from new wars in the region, and Israel looked unlikely to pursue the war unilaterally. Iran still kept up its brutal repression of its own people to maintain its grip on power, and it funded and ordered terrorism and militancy throughout the Middle East to assert its role as a regional power. What’s more, it pursued an aggressive military build-up — making clear that it would no longer need to rely on waves of cannon fodder to defend itself. All told, the nuclear sabre became less necessary to rattle.6
This all made for a remarkably complicated problem. Iran’s sponsorship of terrorism in the region is driven by ideology, theology, strategic positioning: Meaning it is incredibly hard to stop, short of ousting the regime in Tehran. At the same time, its sturdy domestic repression system made fomenting revolution hard and its professionalizing military made invasion costly. In fact, its wily realpolitik made it tricky to do much of anything. Even reapplying economic sanctions could trigger a restart of its nuclear program. Combating Iran’s regional terrorism and constraining its military capabilities was important — but there was no easy solution to do either.
And so, the West played the game and the regional conflict remained at a low boil. It was, by no means, perfect: But it sure beat all-out war.
Anyone who acknowledges those facts has a hard time making a case to invade Iran. So Netanyahu and Trump have simply never bothered to.
Israel has been assassinating Iranian nuclear scientists and launching cyber attacks on its nuclear infrastructure for decades, insisting that these attacks are the only thing keeping Iran from getting the bomb. Netanyahu has insisted for his entire political career that Iran isn’t just hell-bent on obtaining a nuclear weapon but that it hoped to do so imminently, and to destroy Israel in a unilateral strike.
“Within three to five years,” Netanyahu, said in 1992, then just a member of the Knesset, warned, “we can assume that Iran will become autonomous in its ability to develop and produce a nuclear bomb.” (In reality, even after another decade of working in total secrecy, Iran was nowhere near obtaining the bomb.)
Trump agreed. He declared the JCPOA “catastrophic” and insisted it did nothing to constrain Iran’s nuclear ambitions and, once in office, tore it up. Iran actually worked to preserve the deal but, as American sanctions returned, Iran went right back to enriching uranium.
So it became an official tenet of the Trump-Netanyahu Doctrine that Iran was an imminent threat. It was said so often and in so many different ways that it became a truism. And the pair did everything they could to ensure that it was a self-fulfilling prophecy.
It did not filter down to the Pentagon, however. In 2019, the Defense Intelligence Agency reported that “Iran’s conventional military strategy is primarily based on deterrence and the ability to retaliate against an attacker.” Reviewing its capabilities, operations, and its nuclear program, the intelligence agency wrote:
DIA: Iran’s “way of war” emphasizes the need to avoid or deter conventional conflict while advancing its security objectives in the region, particularly through propaganda, psychological warfare, and proxy operations. Iran’s deterrence is largely based on three core capabilities: ballistic missiles capable of long-range strikes, naval forces capable of threatening navigation in the Persian Gulf and Strait of Hormuz, and unconventional operations using partners and proxies abroad.
Trump, as it happens, once claimed that these efforts to defer invasion are exactly why the U.S. should invade. “They’ve been beating us psychologically, making us look a bunch of fools,” he declared in 1988. If he were commander-in-chief, he said, “I’d do a number on Kharg Island. I’d go in and take it.” (Kharg Island is an island seaport for Iran’s oil industry with no particular strategic utility.)
It didn’t reach the intelligence community, either. In 2025, the Director of National Intelligence’s annual report plainly observed that “Iran is not building a nuclear weapon and that Khamenei has not reauthorized the nuclear weapons program he suspended in 2003, though pressure has probably built on him to do so.” That observation, when repeated by Director of National Intelligence Tulsi Gabbard, threw the Trump administration into a tizzy. Trump and Vice President JD Vance simply insisted the intelligence was all wrong, or that Iran had quickly started building a bomb in the gap between its publication and their decision to bomb it in June of that year.
When Washington did join Israel in bombing Iran last year, it was a performative show of force — a series of strikes on the nuclear sites Iran had rebooted since Trump ripped up the JCPOA deal. The bombing achieved through kinetic means what Obama wanted to do through negotiation: It collapsed Tehran’s ability to enrich and stockpile uranium.
Over those 12 days last year, Iran also got to show its strength to the region. It unleashed waves of missiles on Israel, shaking faith in the country’s Iron Dome interception system and killing dozens.
I can’t imagine Tehran walked away from that war happy. But Iran delivered a response that underlined its willingness and ability to rain hell down on its adversaries if provoked — exactly as American intelligence assessments said it would do.
With the bombing over, Trump returned to his longstanding position: That a better deal with Iran is possible, but only if he is the one making it. So Trump’s cronies, Jared Kushner and Steve Witkoff, trudged to Oman to meet their Iranian counterparts.
And, by late February this year, it seemed the whole strategy paid off. According to Oman, who mediated the talks, a new nuclear deal was “within our reach.” The Americans had even convinced Iran to agree to the piece that Obama couldn’t even nail down: “We are talking about zero stockpiling,” the Omani foreign minister told CBS. Iran would limit enrichment only to levels required by its civilian nuclear power plants and convert it all directly into nuclear fuel. Tehran even signalled its openness to limiting its missile program.
Not everything was hammered out. Kushner and Witkoff hadn’t brought a nuclear weapons expert with them, so parts of the deal were yet to be fleshed out. But when the UK’s national security advisor arrived at the talks, he was “surprised by what the Iranians put on the table,” an official told The Guardian.
“It was not a complete deal, but it was progress and was unlikely to be the Iranians’ final offer. The British team expected the next round of negotiations to go ahead on the basis of the progress in Geneva.”
The date of those Swiss negotiations had been set. But they never happened. Because, two days later, Israel and the United States began bombing. The negotiations were, according to Israeli officials, a “deception exercise.” Per the New York Times and others, Netanyahu and Trump had settled on war as the likely outcome weeks before.
The casus belli for this new war was, like the old one, Iran’s dreaded nuclear program. Both leaders insisted that Iran posed an imminent threat to Israel and the broader Middle East, and that intervention was a necessary step to stop Iran before it nuclearized.
That claim was, once more, undercut by the intelligence community. But, this time, Gabbard had the good political sense to try and censor the intelligence — even if she didn’t do a very good job. Below is the difference between what her prepared remarks said (struck-through) and what she actually read into the record (in bold.)
Gabbard:
As a result of Operation Midnight Hammer, Iran’s nuclear enrichment program was obliterated. There has been no efforts since then to try to rebuild their enrichment capability. The entrances to the underground facilities that were bombed have been buried and shuttered with cement. We continue to monitor for any early indicators on what position the current or any new leadership in Iran will take with regard to authorizing a nuclear weapons program.Prior to Operation Epic Fury, the IC assesses Iran was trying to recover from the severe damage to its nuclear infrastructure sustained during the 12-day war and continued to refuse to comply with its nuclear obligations with the IAEA, refusing them access to key facilities.
Lying is integral to geopolitics. You can’t compete with rivals if you can’t lie.
But, looking back, we know that Kennedy and Khrushchev lied to avoid war. Here, we can plainly see that Trump and Netanyahu are lying to instigate it.
Let’s quickly recap this war.
At the outset, Trump insisted the bombing would only last for about a week. Then it was “four to five weeks,” but it could end faster, yet there would be “no timeline” for the war’s end, but by a month in, it might need another “two to four weeks,” or maybe “two to three weeks.” Trump insisted Iran was begging to negotiate a deal, that a deal was being worked out, then said he would accept only “unconditional surrender.” As the bombing went on, Trump declared the war “complete, pretty much,” but it was only “just beginning” but also it was “very nearly complete,” then that he said he “hadn’t won enough.” The objectives had been achieved early on and “from a military standpoint, they’re finished.” He insisted there must be total regime change, then said he wanted to pick a new Ayatollah, then said he was “disappointed” with the Ayatollah the mullahs selected without him, before declaring the regime change complete anyway. Trump insisted that Iran could not be allowed to control the Strait of Hormuz, then said it would be fine if they did, then declared it wasn’t fine, then offered to split the profits. He said the Strait would ”naturally” open, then demanded help in opening it, then proposed renaming it the Strait of Trump, then said it might just remain closed, then demanded it be opened, then celebrated its reopening after an initial ceasefire, then blockaded Iran’s renewed blockade, then declared it open even though it was closed. He said the war was going “swimmingly,” then hectored NATO countries which didn’t come to his aid, then threatened to do genocide.
Nearly two months after the war began, Trump’s effort is a damning fuckup. Iran’s missile program remains a major threat to the region, particularly as air-defenses run low. Iran’s navy may be hobbled, but its small-and-agile fleet of patrol boats have kept the Strait of Hormuz closed. Tehran now asserts sovereignty over the Strait, a major new victory for the regime — which appears sturdier than even before the war. Iran’s clients abroad appear even more emboldened to attack, particularly as Israel continues its scorched-earth military campaign in Lebanon.
In short, the only objective Trump has actually accomplished is in destroying Iran’s nuclear program — which he did last year.
Kennedy and Khrushchev averted catastrophe because each man understood the other’s constraints, aspirations, and weaknesses. Visibility wasn’t perfect, but a rough understanding of how the other man approached the chessboard allowed for strategies that weren’t zero-sum.
This war is stupid not just because it was built on a lie, not just because it was prosecuted with no clear objective nor plan, and not only because it was conducted in a way that has shown no concern for civilian life — but because it was ordered by a man with a pathological belief that he knows better than everybody else.
To iterate on a famous line from Kennedy: Trump launched this war not because it was easy, but because he thought it would be easy.
Anyone who understands Iran’s motivations, however, would know that this clusterfuck was the likely outcome. Trump didn’t care, because he has been telling himself for four decades that he understands these things better than anybody else. Winning a war against an entrenched opponent from the air is notoriously difficult, which the Pentagon told him. The regime has a distributed and ruthlessly effective militia network which had made democratic overthrow incredibly difficult, which his spies warned him of. The Kurds were always unlikely to get too involved, Israel was always unreliable in its assessments of Iranian military power, and Netanyahu has long been well-known to oversell Israeli warfaring capabilities — things that were aduntantly clear from the outset. Even taking Kharg Island has proved more difficult than he once imagined.
Most critically: Analysts have long noted that, backed into a corner, it would be in Iran’s interests to lash out as violently as possible. Challenged at home and abroad, Tehran was incentivized to show just how fanatical and dangerous it could be. It was in Iran’s interest to inflict costs on America, Israel, and the whole region. If the theocracy could survive the war, it wanted to leave a singular message in the minds of world leaders: Attacking us is not worth it.
This has been Iran’s military doctrine since the 1980s. This is not a secret.
But Trump, drunk on his list of minor military successes — killing Qasem Soleimani, kidnapping Nicolas Maduro, bombing Iran’s nuclear sites the first time — genuinely thought this war would go well. He thought his own gut feelings meant more than the mountain of intelligence and military advice provided by his spies and generals. And he seemed very sure that AI could smooth over all the problems inherent in his murderous gambit — the utility of that was made clear in the early hours of the war, when American missiles hit a girls’ school which had probably been misidentified by AI as a military site. More than 170 children were killed.
Since then, Trump and Netanyahu have experimented with bombing different things to see if it could provide a shortcut to victory. They have hit bridges, factories, pharmaceutical facilities, schools and universities, mosques and synagogues, and a host of other civilian infrastructure.
Next up, should this ceasefire fail, will be power plants and water desalination facilities. Perhaps he’ll go further, reviving his threat that “a whole civilization will die tonight, never to be brought back again.”
Maybe the ceasefire will hold. But given that Trump has handed Iran an enormous amount of leverage, it seems clear that either America must make concessions or continue fighting. Both outcomes were avoidable.
The world is here because Trump is temperamentally ill-suited to being president. This, I know, isn’t a terribly bold statement. But that fact is no longer a problem which can be constrained or muddled through. The president has made clear that he intends to use the U.S. military to achieve his half-baked aims at whatever cost. That is terrifying.
Trump’s efforts to occupy U.S. cities, to rig the elections, and to enrich himself — amongst his other litany of abuses and corruptions — are being resisted through democratic and legal channels. We’ll find out in November how that goes. But the people of Iran don’t have the luxury of going through those American channels. They are facing bombardment now. And we don’t know who will be next, though Cuba seems a likely target.
In the hours after Trump threatened to annihilate the people of Iran and his last-minute declaration of a cease-fire, it seemed that lawmakers in Washington were finally coming around to the tools at their disposal to stop him. Outgoing Representative Marjorie Taylor-Greene even raised the idea of invoking the 25th amendment, which would see Trump’s cabinet declare him incompetent. Democrats, meanwhile, have prepared articles of impeachment.
Yet Congress can’t even pass a vote calling for the illegal war to end.
The mismatch between what U.S. legislators should be doing and what the majority are doing is disquieting.
When the world teetered close to nuclear annihilation in 1962, we avoided extermination because relatively sensible leaders acted relatively sensibly. Trump, by contrast, isn’t behaving rationally, has no idea what he wants, and seems willing to commit mass murder in the name of declaring it a win — and nobody seems keen to stop him.
Had anyone in a position of power during the Cuban Missile Crisis acted this stupidly, we’d all be dead.
That’s it for this dispatch.
Here’s my regular mea culpa for the slow pace of dispatches. I was knocked on my ass by a cold earlier this month that really screwed up my publishing schedule.
Rest assured, the Strait of Bug-eyed and Shameless has reopened and regular traffic has resumed.
Over in the Star, I argue that Mark Carney has cobbled together an unconventional national unity government, that Canada can (and should) seize billions in Russian assets, and that Danielle Smith’s most recent dalliance with anti-Semitic conspiracy theories should worry us.
Until next time!
Nuclear Folly: A History of the Cuban Missile Crisis, Serhii Plokhy (2021)
Nuclear Iran: Perils and Prospects, Jahangir Amuzegar (Middle East Policy, Summer 2006)
Exploring the Driving Forces Behind Iran’s Nuclear Deterrence Strategy: A Novel Methodological Approach, Mohammad Eslami (Journal for Peace and Nuclear Disarmament, 2024)
Iran and Nuclear Weapons Production, Paul Kerr. (Congressional Research Service, 2026)
Iran: Nuclear Intentions and Capabilities, Director of National Intelligence (2007)
Nuclear Weapons and Iranian Strategic Culture, Jennifer Knepper (Comparative Strategy, 2008)