Cuba Is Next: Inside Washington's Pressure Campaign to Topple Havana

In a year that just keeps producing crises, the war in the Middle East has dominated the headlines—but in its shadow, a quieter campaign has been building toward what is shaping up to be the next domino: an American operation against Cuba. President Donald Trump has described what might be coming for Havana as a “friendly takeover,” and his administration is laying the groundwork for it methodically.

The effective siege Washington has imposed since January is starting to bite in ways that are difficult to overstate. February 2026 was the first month in over a decade in which the island received zero oil imports from any source—not less than usual, not a reduced trickle, but nothing at all. Conditions have reached a point where planes cannot land in Cuba because there is not enough fuel to get them airborne again, and hospitals have indefinitely suspended virtually every non-life-threatening procedure.

Yet the fall of the regime in Havana has been unsuccessfully predicted for more than half a century. With the United States preoccupied by the largest military operation it has run since the 2003 invasion of Iraq, the obvious questions are what this pressure campaign really means for the island—and whether Cuba will truly become Trump’s next military target.

Key Takeaways

February 2026 was the first month in over a decade in which Cuba received zero oil imports from any source, leaving the national grid running at roughly half capacity on its best days.
Executive Order 14380, issued on January 29th, authorized tariffs on all imports from any country that directly or indirectly supplies oil to Cuba—pressure that pushed Mexico, the island’s largest supplier, to halt crude shipments.
Washington’s strategy is conspicuously non-military: officials are betting that the regime’s legitimacy is rotting faster than it can patch the holes, making patience far cheaper than an invasion.
Backchannel talks—dubbed “Cubastroika”—have reportedly explored loosening sanctions in exchange for a negotiated political exit, with Secretary of State Marco Rubio’s counterpart being Raúl Castro’s grandson.
The regime’s survival now hinges on whether its security forces stay cohesive—the same reserves that fund the officer corps are the reserves approaching depletion.

The answer, on current evidence, is that Washington believes it can break the Cuban government without an invasion at all—by starving the regime of fuel, dollars, and escape routes until it either negotiates its own exit or is forced out from below.

The Siege Tightens

Cuba entered this year already in rough shape: rolling blackouts were a daily fixture of life, the economy was in shambles, and the grid had suffered multiple nationwide collapses over the previous year that the government barely managed to patch back together each time. The turning point came with the arrest of Venezuelan President Nicolás Maduro, which severed Havana’s energy lifeline in Caracas.

What followed in the months since was an even more expansive campaign to cut off every dollar, every barrel, and every escape route the regime had left. The cutoff of Venezuelan oil turned out to be only the beginning. An island that had spent years scraping by suddenly found its largest remaining supply lines targeted one after another, in a sequence designed to leave no alternative standing.

The result is a country running out of nearly everything at once—fuel, hard currency, and food simultaneously. That convergence raises the central question of the entire operation: what, exactly, is Washington’s goal?

Mexico, Oil, and Executive Order 14380

One development that had largely gone unnoticed was that Mexico overtook Venezuela as Cuba’s largest oil supplier over the past year. In the immediate aftermath of the Maduro operation, Mexican President Claudia Sheinbaum initially committed to honoring existing contracts—not increasing them, but delivering what had already been signed—framing the issue as both a sovereign and humanitarian matter. To her credit, one tanker did arrive in Havana in January.

It was still a fraction of what the island actually needed, and even that would not last. On January 29th, the Trump administration issued Executive Order 14380, declaring a national emergency that empowered the president to impose tariffs on any country that “directly or indirectly” sells or provides oil to Cuba. The critical detail was the scope: the order authorized additional duties on all imports from offending countries, not just energy products.

For Mexico, that meant continued shipments to Havana risked triggering penalties across the entire USMCA trade relationship almost immediately. Sheinbaum acknowledged shortly afterward that deliveries were “currently halted,” describing it as a sovereign decision amid “fluctuations”—but the timing left little mystery about what was really behind the move. Mexico pivoted to humanitarian aid only, shipping food and medicine while zero crude moved to the island.

Choking the Last Channels

Havana is not entirely isolated on the world stage. Russia has made sporadic attempts to run tankers through, but US threats against third-party shippers have deterred anything meaningful, at least so far. The physical infrastructure to process what little might arrive is disappearing as well: a refinery fire on February 13th temporarily put the plant out of commission, and even before that, the island’s field reserves had dwindled to the point that commercial flights were largely cancelled as airports simply ran out of jet fuel.

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The oil blockade has drawn the headlines, deservedly so, but it sits atop a financial strangulation campaign that has in some ways been even more methodical—and much of it was already in motion before Maduro was ever arrested. The Cuba Restricted List, which bars American citizens and entities from transacting with hundreds of military- and intelligence-linked Cuban organizations, was reinstated on day one of the second Trump term.

The administration wasted little time expanding it. Orbit, one of the last remaining channels through which US dollars were still reaching the island in the form of remittances, was added—effectively severing the last inflows of foreign currency.

Doctors, Tourists, and Hard Currency

Beyond finance, the administration has also targeted the regime’s two biggest non-oil sources of hard currency: Cuba’s medical brigade program and tourism. The medical brigade program sends doctors abroad in what critics describe as a forced-labor export scheme. To choke it off, new visa restrictions now target Cuban and third-country officials involved in administering these programs, aiming to cut the pipeline off at its source.

Tourism, the other lifeline, has been hit from two directions: travel restrictions that were reimposed and tightened, and the fuel shortages that threw most of the country into chronic rolling blackouts. Together, those make for something well short of a luxury getaway. A destination where the lights go out for the better part of a day, the water stops, and the trash piles up is not one travelers flock to.

The combined effect is an economy stripped of nearly every external source of revenue at once. With oil cut off, remittances severed, the medical missions squeezed, and tourism collapsing, the regime has been left with vanishingly few ways to bring in the currency it needs to function.

The Strategy: A “Friendly Takeover”

The speed at which the administration’s rhetoric has escalated tells much about where Washington thinks this is headed—and the confidence it has in getting there. On January 3rd, the day of the Maduro raid, when analysts were still scrambling to figure out whether it signaled a broader regional campaign, Trump was almost casual about future relations with Havana: “I think Cuba is going to be something we’ll end up talking about, because Cuba is a failing nation right now.” A day later, he waved off the idea of military action entirely, saying it would not be necessary because “it looks like it’s going down” on its own.

By March, the tone had shifted, and the president began using the phrase “friendly takeover” for the first time. What is striking is how little of the strategy behind that rhetoric actually involves the military. That is partly explained by Washington being engaged in its largest military operation since 2003—but only partly. It was clear well before the Middle East buildup that the United States had set its sights on Tehran militarily, which simply is not the case with Cuba.

The Berlin Wall Bet

Representative Carlos Giménez, one of the most hawkish Cuban-American members of Congress, titled an op-ed “Cuba Is Approaching Its Berlin Wall Moment.” Part of what made the fall of the Berlin Wall so famous was that it did not involve a military deployment, but rather a popular movement of the people after the system around it had rotted out.

That is the bet Washington appears to be making: that the Cuban regime—and its legitimacy—is rotting faster than it can patch the holes, and that patience costs essentially nothing while an invasion would cost a great deal. Based on the numbers, the logic is hard to argue with. With February 2026 the first month in over a decade of zero oil imports, the grid is running at half capacity on its good days, and analysts warn that complete fuel depletion could arrive within weeks.

The pressure extends well beyond energy. In late February, Secretary of State Marco Rubio flew straight from Trump’s State of the Union address to a CARICOM summit—a bloc that had long been one of Havana’s most reliable allies for over fifty years. By day’s end, Rubio told reporters that virtually every leader in the room agreed Cuba’s status quo was “unacceptable.”

Cubastroika and the Castro Grandson

The question, then, is not whether the pressure campaign is working—it clearly is, insofar as it is making life miserable on the island. The real question is whether that pressure can actually produce a change in government. There are indications the administration believes it can. Sourced to officials with direct knowledge of the talks, reporting has described active backchannel negotiations for what some are calling “Cubastroika”—a plan in which the US would loosen sanctions on energy, ports, and tourism and allow direct American investment in exchange for a negotiated political exit for President Miguel Díaz-Canel.

The man Rubio has been talking to is none other than Raúl Castro’s 41-year-old grandson—believed to be the one set to oversee GAESA, the military conglomerate at the heart of the Cuban economy. GAESA’s scale is difficult to overstate: its gross profits represent close to 37 percent of Cuba’s GDP, its exports account for roughly a third of the island’s total, and its total revenues are more than three times greater than the entire Cuban state budget. Leaked documents have reportedly shown the conglomerate holding as much as 18 billion dollars in hard currency, a sizable portion of the ailing island’s total annual GDP.

But critically, the plan as described lacked any framework for a democratic transition—no free elections, no opposition parties, no human rights overhaul. The exile community has not been thrilled. José Daniel Ferrer, one of Cuba’s most prominent opposition leaders in exile, warned Rubio directly against any Venezuela-style pact that preserves the regime’s power structure, saying such a move would be a mistake that invites new crises down the road.

The Human Toll of “Zero Hour”

For most people, “rolling blackouts” call to mind the occasional storm-driven outage—a nuisance, a day without a charged phone. What is happening in Cuba is a different universe. On March 4th, the Guiteras thermoelectric plant—the same aging facility whose collapse in October 2024 plunged most of the island into darkness—went down once again, this time taking two-thirds of the country with it. It was repaired within four days, but the grid that came back online was still running at less than half the country’s demand.

During the crisis, Cuba was producing around 1,200 megawatts against a need for over 2,200, and blackouts that once lasted 12 to 14 hours have now stretched past 20. In effect, chronic mismanagement and a two-month blockade have done to Cuba’s power grid what it took the Kremlin four years of constant bombardment to do to Ukraine’s.

Daily life has reverted to something closer to pre-industrial. Refrigerators are next to useless, so perishable food often cannot be stored. Most of Havana’s garbage trucks sit idle without fuel, so trash piles up for weeks and ultimately gets burned in the streets. Over 80 percent of the country’s water-pumping infrastructure runs on electricity, meaning that when the power goes, so does the water—and close to a million Cubans depend on tanker trucks that themselves need fuel to operate.

Families fill buckets during the few hours of daily power, racing to finish basic tasks before the lights cut out again.

A System on the Brink

At the institutional level, conditions are as severe, if not worse. Hospitals have more or less suspended non-emergency surgeries nationwide, and the healthcare system once held up as the pride of the regime is operating, by the Health Minister’s own admission, on the verge of collapse. The UN’s humanitarian office reported that some 16,000 cancer patients awaiting radiotherapy and over 12,000 dependent on chemotherapy are unable to receive treatment, while ambulances across the island struggle to obtain fuel for emergency runs.

Analysts have begun using the term “zero hour” for the moment the reserves finally run dry, with reporting pointing toward mid-to-late March 2026 as a likely timeline. Given that this assessment was made on March 11th, that moment was not far off.

Washington’s bet is that conditions like these will eventually produce one of two outcomes: either the regime negotiates its own exit, or the Cuban people force one. On the surface, the theory makes some sense, even if it is grim for the people there and will almost certainly lead to loss of life. In the days after the March 4th blackout, protests erupted across multiple Havana neighborhoods and spread to cities like Matanzas, with people chanting “Freedom!” and “Down with communism!”

Why the Regime Is Still Standing

For Cubans who might rather leave than fight, that option has more or less dried up. Allowing critics of the government to leave the country was for years a not-so-secret release valve—one fewer potential dissident or rioter in the street. Since 2021, the easiest route was via Nicaragua, whose visa-free policy had been a head-nod to those seeking a foothold on the continent from which they could head north. On February 8th, Managua quietly revoked the arrangement, a move widely read as a concession to Washington after Maduro’s capture left the Ortega regime increasingly isolated.

That leaves ordinary Cubans with essentially two options: endure, or take to the streets. The regime has spent years making sure they know what the second one costs. The last large-scale protests, dating to 2021, still loom large; over a thousand people were arrested then, and many are still serving sentences of 15 to 20 years for little more than chanting slogans—including children.

Cuba watchers sometimes invoke North Korea to explain how a government this battered can still be standing. The analogy is imperfect—the Cuban regime is nowhere near as brutal as the one in Pyongyang—but it offers something. Pyongyang demonstrated decades ago that a regime can survive extraordinary circumstances if its security apparatus remains cohesive, regardless of the population’s opinion. Famine may have killed hundreds of thousands, even millions, of North Koreans in the 1990s, but the Kim family did not blink.

The Men With Guns

When it comes to most uprisings against dictators, the fatal blow usually is not a mass protest but the state losing confidence in itself—no longer being willing to pull the trigger on its own people. As of March 11th, there was no credible reporting of defections within Cuba’s security services. Part of that comes down to the regime’s strategy to insulate itself: a late-2025 decree expanded military benefits, while supplies for defense-related units are explicitly prioritized ahead of civilian needs in the emergency rationing plan. So far it has paid off, with the state’s rapid-response units deploying to every protest hotspot without reluctance.

Then there is the Iran example. The regime in Tehran showed despots everywhere that you can put down enormous nationwide protests in days, so long as you keep the military onside and are willing to kill in eye-watering numbers. Havana has never yet engaged in a crackdown remotely as brutal, but the overall lesson of reacting harshly will not have passed it by.

Still, things may be changing. The Cuban regime has always paid and fed the apparatus first—but this time, the reserves funding the officer corps are the same reserves approaching zero hour. And once that hits, there is nobody coming to replenish them.

Every regime that has fallen to popular pressure has shared one thing: a moment when the people holding the guns decided the people giving the orders were not worth dying for anymore. If Cuba does not reach a deal with Washington by “zero day,” that commitment will be put to the test—and only then will it become clear whether the next step is a peaceful transition, a revolution, or the seeds of yet another military intervention.

Presented by

Simon Whistler

Simon Whistler is one of YouTube's most prolific educational creators. WarFronts is his deep dive into military history and conflict analysis.

Frequently Asked Questions

What was significant about Cuba’s oil imports in February 2026?

February 2026 was the first month in over a decade in which Cuba received zero oil imports from any source. It was not a reduction or a shortfall—nothing arrived at all, leaving the grid running at roughly half capacity on its best days and pushing the country toward complete fuel depletion. Analysts began using the term “zero hour” for the moment Cuba’s reserves would finally run dry, with reporting pointing toward mid-to-late March 2026 as a possible timeline.

What did Executive Order 14380 do, and how did it affect Mexico?

Issued on January 29th, the order declared a national emergency empowering the president to impose tariffs on any country that “directly or indirectly” sells or provides oil to Cuba. Crucially, it authorized additional duties on all imports from offending countries, not just energy products—meaning Mexico’s continued shipments risked penalties across the entire USMCA trade relationship. Mexican President Claudia Sheinbaum shortly afterward acknowledged that deliveries were “currently halted,” while Mexico pivoted to shipping only humanitarian food and medicine.

What is “Cubastroika” and who is involved in the reported negotiations?

“Cubastroika” is the name given to reported backchannel negotiations in which the United States would loosen sanctions on energy, ports, and tourism and permit direct American investment in exchange for a negotiated political exit for President Miguel Díaz-Canel. Marco Rubio’s reported negotiating counterpart is Raúl Castro’s 41-year-old grandson, believed to be in line to oversee GAESA—the military conglomerate whose gross profits represent close to 37 percent of Cuba’s GDP. The plan as described lacked any framework for free elections, opposition parties, or a human rights overhaul.

Why hasn’t the Cuban regime collapsed despite the severe crisis?

Its security apparatus has remained cohesive. A late-2025 decree expanded military benefits and prioritized defense units in emergency rationing, and rapid-response units have deployed to every protest hotspot without reluctance. Escape routes have also been closed off: Nicaragua revoked its visa-free policy for Cubans on February 8th, leaving ordinary Cubans with the choice of enduring conditions or taking to the streets—a prospect made stark by memories of the 2021 protests, after which over a thousand people were arrested and many received sentences of 15 to 20 years.

Is the United States planning a military invasion of Cuba?

On current evidence, no. Trump waved off military action early on, saying Cuba “looks like it’s going down” on its own, and the administration’s strategy has been conspicuously non-military. Washington’s bet is modeled on the fall of the Berlin Wall—that the Cuban regime’s legitimacy is rotting faster than it can patch the holes, making patience far cheaper than an invasion, especially while the US is already engaged in its largest military operation since 2003.