Cuba has been Russia’s closest foothold in the Western Hemisphere for decades. Back in the Soviet era, Moscow kept Fidel Castro afloat with massive subsidies—not out of love, but for one reason: a lever against the United States.
That lever almost snapped the world in half in 1962, during the Cuban Missile Crisis—when a small island turned into the most dangerous chess square on Earth.
And now Cuba is in the headlines again.
With Trump’s recent talk, people are asking the same nervous questions: Are we heading toward Bay of Pigs 2.0? A new missile crisis? Is history looping back—just with different faces on the posters?
Today, we’ll look at what Russia wants from Cuba right now, what it’s willing to offer in return, and why this situation is fundamentally different from 1962.
Here’s our roadmap:
* Missiles Near Miami – The original Cuban Missile Crisis and how it changed Cuba, Russia, and the US.
* Subsidies Building Havana – How Castro’s regime survived on the Soviet aid.
* Fists for Hire – How Cuba returned the favors by renting out its military.
* When Subsidies Died – What happened to Cuba after the Soviet Union collapsed.
* Fuel Is Politics – How oil imports from Venezuela became Cuba’s new lifeline.
* Leverage, Not Love – What the Russian-Cuban relationship looks like today.
* Tomahawks and Signals – Why the Kremlin’s response to Trump’s announcement about Tomahawks for Ukraine involved Cuba.
* The Collapsing Club – Why Cuba’s main problem is being part of the informal “dictators’ club.”
Missiles Near Miami
In 1959, Fidel Castro took power on a promise of dignity and justice. Within a few years, he locked Cuba in a direct confrontation with the United States.
In April 1961, the Bay of Pigs invasion failed. But Havana realized just too well that the next attempt might be bigger, and it might succeed.
So Cuba wanted a shield. And the Soviet Union wanted a forward position in a location where it could directly threaten the US, its biggest geopolitical rival.
That is how you get to 1962. Moscow secretly sent nuclear-capable missiles to Cuba. For Khrushchev, this was about changing the map. If you can place weapons near Florida, you can force Washington to treat you like an equal.
The United States discovered the missiles through U–2 reconnaissance flights. Then Kennedy ordered a blockade, calling it a “quarantine,” because even the vocabulary was dangerous.
For thirteen days, the world lived in fear of a nuclear war breaking out. The worst moment was October 27, when a U–2 was shot down over Cuba and the pressure spiked.
The crisis unfolded much like a staring game, but it didn’t end because anyone blinked. It ended because both sides found a common ground.
The public part of the deal was simple. The Soviet Union would remove the missiles from Cuba. The United States would pledge not to invade Cuba.
The private part was the key. Khrushchev demanded something he could sell at home: the removal of American Jupiter missiles from Turkey. Kennedy did not want that to look like a swap under pressure. So the United States quietly agreed to remove those Jupiters later.
Those missiles were, in truth, already seen as obsolete. But such a deal, if made public, would still make him look bad on television.
After the crisis, both sides added guardrails, because they understood how close they came. The hotline came soon after, and crisis management became its own kind of weapon.
And Cuba? Cuba learned that when you let someone else place their big weapons on your soil, you become a battlefield without firing a shot. But still Havana didn’t walk away from its dangerous “friendship” with the Soviet Union. This friendship was Castro’s only chance to keep the country in his hands.
Subsidies Building Havana
Castro stayed in power because Cuba got a patron that could replace the American market it had just lost. The US embargo didn’t disappear but it stopped being decisive when the Soviet bloc stepped in as a substitute.
To stay part of this ecosystem, Cuba didn’t have to become efficient. It only had to stay loyal.
The core trade was deeply political. Cuba exported sugar, and later nickel and other raw materials. The Soviet Union and the socialist bloc bought those goods on significantly better terms than the free market would offer. In return, Cuba got oil, machinery, and loans. In 1972, Cuba joined COMECON, which made this arrangement more structured.
This is where many Western observers get lost. They look at the embargo and assume it should have crushed the regime.
But an embargo works only when the target is isolated. And Cuba was connected with socialist states on the other side of the globe.
The Soviet Union also kept supporting Castro’s regime with military cooperation. The Cuban forces got training and intelligence ties: the kind of assistance that doesn’t make headlines.
And there is one more part that matters for today. The debt.
Over decades, Cuba accumulated a massive Soviet-era debt. After the USSR collapsed, that debt became a ghost argument that poisoned the relationship with Russia for years.
Then Moscow made a strategic decision. In 2013–2014, Russia agreed to write off 90 percent of Cuba’s Soviet-era debt, commonly reported as roughly $32 billion out of about $35 billion. Cuba would repay the remaining few billions over time.
Why did Moscow do that?
Not out of charity, but because it still needs Cuba for the same purpose the Soviet Union needed it for: as a lever close to the United States’ border.
Fists for Hire
Moscow wanted reach without risk at home. Havana wanted money, protection, and a mission that could be sold as glory, not dependency. So Cuba became something like a hired fist for a patron who preferred to stay in the shadows.
Angola is the cleanest example. In late 1975, Cuba rushed troops to support the local socialist government in the civil war. Roughly 36,000 Cuban soldiers arrived to Angola over the next few months. By the late 1980s, Cuba had tens of thousands of troops in Angola, and the fighting of Cuito Cuanavale became one of the symbolic peaks of that long intervention.
For Moscow, that was clean leverage. If Cubans fight, the Soviet Union gains influence without putting Soviet conscripts in African graves. Havana benefitted as well, just in a less obvious way. A small, sanctioned island suddenly gets to act like a world power. That feeling helped the regime look taller than it was.
Ethiopia is the second example. In the Ogaden War, Soviet support and a large Cuban deployment helped Ethiopia reverse the battlefield. Declassified U.S. intelligence reporting from the period describes a Cuban expeditionary force of around 17,000 providing the cutting edge for the counteroffensive.
Now ask the awkward question: was Cuba doing its own foreign policy, or was it rented out?
The honest answer is “both,” and that’s exactly why it worked. Castro had his own ideology and his own ego. He did not need Moscow to tell him that backing fellow revolutionaries was good propaganda. But the planes, the weapons, the fuel, and the long-term resupply depended on the Soviet system. Cuba could be bold, as long as it stayed inside the patron’s budget.
There’s a human detail to that era: those Cuban kids in uniforms, shipped across the ocean, then sent back with scars and silence.
In January 1989, as Cuban forces began pulling out of Angola, Western journalists got to interview Cuban soldiers. One 21-year-old soldier, Blanca Ginarte, said, “If the peace agreement fails… we are willing to come back.” That’s the voice of someone who believes she is defending a noble cause.
And that’s the twist. Cuba’s proxy role didn’t just serve Soviet strategy. It also served Cuba’s domestic control. It gave the regime a heroic story to wrap around an economy that could not stand on its own.
This arrangement worked until Cuba got hit by the worst possible event for any client state. Its patron disappeared.
When Subsidies Died
When the Soviet Union collapsed and COMECON vanished, Cuba lost its main market, its main supplier, and the financial padding that made the whole system feel stable. What followed was the “Special Period,” and the name is almost a joke. There was nothing special about it. It was just scarcity, every day, for years.
You can measure it in calories. The average food intake in Cuban residents dropping from about 3,000 calories per day in 1989 to about 2,100 in 1993. Other studies report even lower numbers in the worst years. You can measure it in blackouts, too, with long daily power cuts becoming part of normal life.
You can also measure it in bodies. A famous line of research used Cuba as a grim natural experiment: people ate less and moved more, because there was no fuel. One study described an average population weight loss of about 5.5 kilograms during the mid-1990s crisis. There also were sharp declines in diabetes and heart disease, before weight regained later and those gains faded.
But numbers still don’t show the lived texture. For that, you need one ordinary scene.
In September 1991, Havana started a program of issuing bicycles to city residents to conserve fuel. An everyday Gonzalez was now riding to work, part of a city suddenly rebuilt around pedals because engines could not be fed. That’s what economic collapse looks like when it hits transportation first: abandoned, rusting vehicles, and a lot of people on bikes.
During the Special Period, Havana tightened control and also opened small pressure valves. The government leaned harder on rationing and policing, but it also allowed limited self-employment and pushed tourism and hard-currency zones.
Still, pressure built. By 1994, the island saw open anger on the Malecón in Havana, the “Maleconazo.” Around the same time, desperate people tried to flee by sea in larger numbers, which led to the tugboat “13 de Marzo” tragedy that took 41 lives.
Cuba never truly recovered from its patron’s collapse. Yes, it adapted and survived by building new income pipes. Tourism. Remittances. Deals with new patrons. And above all, fuel. Because without fuel, nothing moves.
The Prince of the Soviets, a historical novel by Elvira Bary
Fuel Is Politics
Today, the Cuban leadership desperately needs two things: a steady flow of hard currency and fuel, enough to keep the lights on and the streets quiet as the economy pillars are cracking, one after another.
Start with the most fragile pillar: tourism. In 2024, official Cuban figures showed about 2.2 million international visitors to the island: far below the government’s earlier targets and still well under pre-pandemic levels. Fewer tourists mean less hard currency. Less hard currency means less ability to buy fuel and spare parts. Then blackouts get worse, and tourism gets even harder to sell. It’s a loop that feeds on itself.
The second pillar is remittances. Cubans working abroad send money home to their families, for whom this money is often a lifeline. An estimated $2 billion dollars comes to Cuba each year as remittances. But much of this money bypasses the state. Official transfer channels have been unstable recently – for example, Western Union shut down for months. That forced many senders into informal routes. The government tries to capture more remittance dollars through “dollar stores,” but to no avail.
Now the center of gravity: oil.
For years, Venezuela was the key supplier. In the 2010s, it used to provide Cuba with about 100,000 barrels per day. By 2023, however, these exports dropped by near a half: to around 55,000 barrels per day. Between January and November of 2025, Venezuela sent an average of about 27,000 barrels per day, covering roughly half of Cuba’s oil deficit.
Mexico stepped in more than expected. By May 2025, it was sending to Cuba about 20,100 barrels per day of crude and 2,700 barrels per day of oil products, valued around $600 million. But this still isn’t enough.
For years, Cuba benefitted from the global service layer that helps sanctioned countries move their oil. This layer, known as the “shadow fleet”, includes hundreds of ships and shady service providers that handle the paperwork. It operates under a variety of third-country flags, but the real beneficiaries are sanctioned regimes that sit on oil: Russia, Iran and, until recently, Venezuela. I have looked into this operation in another video.
Venezuela used the ”shadow fleet” to sell its oil to Cuba on better-than-market terms. Cuba was getting this oil really cheap as Venezuela didn’t have other major buyers in the region. With Maduro’s fall, this arrangement is no more. International bodies are considering lifting sanctions from Venezuela so it will be able to sell its oil to other markets. It no longer needs Cuba as a loyal customer. And Cuba has no other supplier that can sell it that much oil that cheap.
In January 2026, Reuters quoted a Havana business owner, Mario Valverde, saying, “The repercussions are not going to be very good,” about the loss of Venezuelan oil. That line is the whole story in one sentence. No fuel means no transport. No transport means no repairs. No repairs mean deeper blackouts. And deeper blackouts mean a government that has to spend more on control, because it has less to offer.
And unlike in the 1960s, no one is coming to rescue the regime in Havana. Russia will not do it, for the reasons we’ll now take a look at.
Leverage, Not Love
Russia’s goal in Cuba today is not to “save” Cuba. It’s to use Cuba as a cheap lever in a fight for global dominance: the fight Russia is losing everywhere else.
The lever works because of geography. Cuba is close enough to the United States that any Russian presence there reads like a message. Moscow wants Washington to feel a small itch at home. Not a heart attack, but still, something that forces attention.
That’s why the most visible tool is theater at sea.
In June 2024, a Russian naval group arrived in Havana, including the nuclear-powered submarine Kazan and the frigate Admiral Gorshkov. Cuban officials said the ships carried no nuclear weapons. Russia called it a visit. Everyone else called it a show. A Reuters photo series captured the scene: the submarine sliding into the bay while people watch from the seawall and tourists drift past in vintage cars, like history is looping on purpose.
This is the kind of signal Moscow loves. It is loud enough to make headlines. It is controlled enough to avoid real escalation. It tells the Kremlin’s domestic audience: “We can still scare America.” And it tells Cuba: “We are still here for you.”
Russia can’t bankroll the island the way the USSR did, but it can ship a tanker now and then, or arrange credit, or promise parts for the grid. In March 2024, 90,000 metric tons of Russian oil arrived in Cuba after a year-long hiatus, framed as help with power outages and fuel shortages.
The third tool is access.
Even when nothing dramatic is happening, Cuba is useful for intelligence and communications. A friendly port, friendly officials, a permissive environment for Russian services to operate.
And the fourth tool is symbolism inside the Global South.
Russia wants to show it still has friends despite sanctions. Cuba wants to show it is not isolated. Both sides stage the same photo ops: flags, handshakes, speeches about “historic ties.”
But since Russia stretched itself thin with a full-scale invasion of Ukraine, Cuba became less of an asset and more of a bill.
Every time Cuba’s grid collapses further, the cost of stabilizing it rises. Russia’s economy is already strained by war and sanctions. So Moscow tries to buy influence in small pieces: one fuel delivery, one headline, then back to scarcity. That isn’t helping Cuba much, but that’s all Moscow is willing to spare.
Tomahawks and Signals
In October 2025, President Trump said he might send Ukraine long-range Tomahawk missiles if Russia didn’t move toward settling the war. It was a threat delivered on Air Force One, the way Trump likes to do it: public, blunt, designed to land in Moscow in real time.
Russia reacted like it always does to a threat it can’t fully control: with escalation talk.
Dmitry Medvedev warned that supplying Tomahawks could “end badly,” leaning on the old Russian argument that Tomahawks are hard to distinguish after launch, and that this creates nuclear risk. It’s a familiar trick. Turn a conventional weapons question into an apocalypse question. Make the West feel responsible for the sky falling.
Another part of Russia’s response directly involved Cuba. Amid the Tomahawk talks, Russia’s upper house ratified an intergovernmental agreement on military cooperation with Cuba that had been signed in March 2025.
On November 2, Trump backed off, saying “for now” he was not considering a Tomahawk deal for Ukraine. For Russia, that looked like their Cuban move worked.
When Moscow wants to warn Washington, it has only a few places where a small move looks bigger than it is. Cuba is one of them.
And this is also why Washington keeps circling back to the island. Cuba is close enough to the U.S. coastline to be strategically intolerable in a major confrontation. And if you want to squeeze Cuba, you don’t start with Havana. You start with the fuel line.
That fuel line used to run through Venezuela. That’s why pressure on Venezuela hits Cuba like a punch to the engine.
There’s one more detail worth holding onto. This is not 1962. Russia isn’t placing missiles on Cuba. Moscow’s goal is to create anxiety and distraction without overspending or risking a direct confrontation. The renewed military collaboration agreement achieves exactly that.
So when you see Russian flags in Havana, don’t ask, “Are they about to start a war with America?”
Ask the more realistic question: “What message are they trying to send, and what problem are they trying to dodge?”
The Collapsing Club
Cuba’s biggest problem is that it’s been stuck, for decades, as part of the “dictators’ club”: a network of authoritarian regimes that help each other evade Western sanctions and survive.
And today we’re seeing this club collapsing.
When Bashar Asad’s regime fell in Syria, that was a strong blow to the network. But the capture of Nicholas Maduro, and the escalating protests in Iran, can possibly put an end to it.
Without Venezuelan oil, Cuba’s fuel gap widens beyond repair. The island can’t simply “replace” that supply because suppliers want cash and insurers want paperwork.
That’s why Cuba’s leadership keeps hunting for any patron or workaround it can find. It turns to Russia for help, but the former patron can offer nothing but an occasional batch of fuel. And even this tiny stream might soon dry out because of the events in Iran.
This January, Iran entered a major internal crisis. Two weeks of large-scale protests resulted in more than 500 deaths and a severe crackdown with mass arrests. The protesters have reportedly taken over two cities in the west of the country.
For Putin’s Russia, Iran is a critical partner. When Iran destabilizes, Russia’s “club” of dictators and shadow fleet operation get weaker. Routes get riskier. Money gets nervous. Oil prices jump around. And every partner starts hoarding resources for themselves.
That’s the opposite of the old Soviet era, when Moscow could spend freely on loyal clients because it had a huge system behind it.
Putin doesn’t have that system. He has a war, sanctions, and a shrinking margin.
So the relationship with Cuba is tuned down: Moscow offers just enough to keep the door open, and Havana accepts because it has no luxury of pride.
This is why the last illusion needs to die. Russia is not coming back as Cuba’s patron. It simply can’t afford such a move. What we’re watching is a relationship between two states that both need the West to survive, while cursing the West on TV.
