This week we talk about the Cold War, the Cuban Missile Crisis, and decapitation attacks.

We also discuss Venezuela, Iran, and the Platt Amendment.

Recommended Book: The Will of the Many by James Islington

Transcript

Cuba is a large island nation, about the same size as the US state of Tennessee, which formally gained its independence from Spain in late 1898, following three wars of independence, the last of which brought the US, Puerto Rico, and the Philippines into play against the Spanish when the Spanish military sunk the USS Maine in Havana Harbor, triggering the Spanish-American War.

That conflict, which Spain lost, led to the US’s acquisition of Puerto Rico, Guam, and the Philippines, and it led to a piece of US legislation called the Platt Amendment, which redefined the relationship between the US and Cuba, following the war, making Cuba a protectorate of the United States, the US promising to leave, withdrawing its troops from Cuban soil, only if seven conditions were met, and an additional provision that Cuba sign a treaty indicating they would continue to adhere to these conditions moving forward—making them permanent.

Most of these conditions relate to Cuba’s ability to enter into relationships with other nations, but provision three also says the US can intervene if doing so will preserve Cuban independence, and that Cuba will sell or lease to the US the land it needs to base its naval vessels in the area, so that it can intervene, militarily if necessary, to keep Cuba independent.

The other provisions are largely related to ensuring Cuba stays financially solvent and clean, the former meant to help maintain that independence, so Cuba doesn’t make deals with other nations, perhaps US enemies, in order to bail itself out when financially in trouble, and the latter meant to help prevent the bubbling up of diseases in a not well-maintained Cuba, that might then spread to the US.

These concerns were concerns for the US government because Cuba is very, very close to the US. It’s just over 90 miles away from Key West, Florida, and that means in the mind of those tasked with defending the US against foreign incursion, Cuba has long represented an uncontrolled variable where enemies could conceivably base all sorts of military assets, including but not limited to nuclear weapons.

That makes Cuba, again, in the minds of defense strategists looking to help the US secure its borders, long-term, something like an aircraft carrier slash nuclear submarine the size of Tennessee, located so close to the US that it could take out all sorts of major assets in a flash, long before the US could respond, getting the same sorts of strike craft and missiles to the Soviet Union.

This framing of the situation, and this collection of concerns, is what led to the Cuban Missile Crisis back in 1962, when the US deployed nuclear weapons in the UK, Italy, and Turkey, all of which were closer to major Soviet hubs than the US, and that led to a tit-for-tat move by the Soviets to deploy nuclear missiles to Cuba, both to get their own weapons closer to the US, just as the US did to them with those new deployments, but also to deter a potential US invasion of Cuba, which was a staunch ally of the Soviet Union.

The crisis lasted 13 days, and though then US President Kennedy was advised to launch an air strike against Soviet missile supplies, and to then invade the Cuban mainland to prevent the basing of Soviet nuclear weapons there, he instead opted for a naval blockade of Cuba, hoping to keep more missile supplies from arriving, and to thus avoid a strike on a Soviet ally that could accidentally spark a shooting war.

After this nearly two-week standoff, the US and Soviet leaders agreed that the Soviets would dismantle the offensive weapons they were building in Cuba in exchange for a public declaration by the US to not invade Cuba. The US also secretly pledged to dismantle its own offensive weapons that it had recently deployed to Italy and Turkey, and the weapons they deployed to the UK were also disbanded the following year.

This sequence of events is generally seen as a minor victory for the US during an especially fraught portion of the Cold War, as that secret agreement between Kennedy and Soviet leader Khrushchev meant that the Soviet people and leadership perceived this agreement as an embarrassing loss, and an example of Soviet weakness on the international stage—they blinked and the US got what they wanted without giving much of anything, though of course, again, the US gave a fair bit too, just in secret.

What I’d like to talk about today is a recent escalation in the US’s posture toward Cuba, and what might happen next, as a result of that change.

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In early January 2026, the US military, ostensibly as part of a larger effort aimed at disrupting a network of watercraft that carry drugs from mostly South and Central American drugmakers across the border, into US markets, called Operation Southern Spear, the United States implemented a new blockade aimed at sanctioned oil tankers carrying fuel from Venezuela to, among other destinations, Cuban ports.

Shortly before this blockade was declared, the US seized an oil tanker off the coast of Venezuela, then harassed, boarded, and intimidated other tankers, including one from Russia, that were also dealing in Venezuelan oil—something that US sanctions disallowed, and which the Trump administration had decided to focus on, ostensibly as part of that anti-drug effort, but also seemingly as part of a then-impending mission to kidnap Venezuelan President Maduro, who was then secreted away to the US to face trial, which is where he is, today.

These seizures hit Cuba especially hard because the country is highly reliant on all sorts of imports, much of its income derived from tourism, not manufacturing or raw materials, and fuel coming from Venezuela was especially vital—about 72% of Cuba’s electricity generation comes from oil-fueled power plants, and basically its entire transportation section is reliant on the same.

Venezuela under Maduro also provided oil to Cuba at a discount, subsidizing it because those US sanctions didn’t allow Venezuela to have many other reliable customers, and because the authoritarian governments of these two nations saw each other as fellow-travelers in the region, and thus wanted to keep each other propped up against constant pressure from the US and other democracies in the Americas.

As of March 2026, Cuba has gone without crude oil deliveries for three months, and this has led to waves of flight cancellations and a depletion of tourism, which again, is the country’s most vital income source. As of mid-March, Cuba’s energy grid has also collapsed, which has left about 10 million people without power most of the time, amplifying existing problems caused by the country’s antiquated energy generation and distribution systems.

All of which seems to be according to plan for the second US Trump administration, which announced, as far back as January of this year, that it was seeking regime change in Cuba, and these blackouts have triggered exceedingly rare violent protests against that regime by Cuban citizens; these protests haven’t led to any real change or consequences yet, but they could, with time.

For their part, the Cuban government has said they’ve entered diplomatic talks with the US, and they’ve already agreed to release 51 political prisoners, just as an up-front, good will gesture. But they’ve also said changes to the Cuban political system or government—which is an authoritarian regime with absolute power, and which, like most such regimes, is openly corrupt, those in charge enriching themselves at the expense of everyone else, while keeping control via state-sanctioned violence against its own citizens—they’ve said changing that is non-negotiable, also noting that if there is direct aggression against Cuba by the US, they’ll fight and offer up “impenetrable resistance.’

The change that the US government seeks is reportedly similar to what was accomplished in Venezuela: booting the current leader, but keeping the existing regime, the power behind the publicly visible throne, intact, and then the US government influencing that existing regime from afar.

This deviates from the assumed model, attempted by previous US and other governments throughout history, to boot the leaders of opposing government types and then replace them, and the local system, with something closer to their own. This new approach is possibly what the Trump administration is aiming for in Iran, as well, though it’s difficult to say how well the model will work even in Venezuela, where it’s still early days after the US’s seemingly successful decapitation attack, much less in places like Cuba, where there’s no single central power in the public-facing government, much of that power spread between Communist Party leaders, rather than hoarded by a single individual—a far cry from how things were under Castro during the Cold War.

As of the day I’m recording this, there’s a new wrinkle in this blockade: a Russian oil tanker has been tracked heading along a trajectory that would seem to lead to Cuba, which, if accurate, could put the US and Russia at odds over deliveries to the island once more—though in this case it would be oil instead of offensive nuclear weapons that are on board the incursionary vessel.

This ship may veer off that current course and head elsewhere, or it could be meant to test the US oil blockade, intentionally poking at what seems to be an impenetrable barrier, to see if it’s all just talk. Even if just that one tanker makes it through, it’s carrying enough oil to provide about a week’s worth of energy to...