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Trump’s man in Havana? Cuba looks like Washington’s next regime change target

On March 16, a nationwide blackout hit Cuba amid an unprecedented fuel crisis, the result of a U.S.-imposed oil blockade. In recent decades, Cuba has survived thanks to supplies from Venezuela, but those ceased after the overthrow of Nicolás Maduro by U.S. forces earlier this year. Public life in Cuba has been paralyzed: schools are closing, air travel has been largely suspended, and civil unrest is on the rise. Meanwhile, American authorities are hinting at the possibility of removing the island’s socialist government. Until recently, the Cuban leadership denied any negotiations with the White House, but media reports have repeatedly pointed to informal contacts between officials in Washington and younger members of the Castro family.

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After Fidel Castro and his barbudos (lit. “the bearded”) overthrew the military dictatorship of Fulgencio Batista in 1959, Cuba became a symbol of independence for many Latin American countries, earning the proud nickname “the island of freedom.” However, it soon became clear that freedom did not equal democracy, let alone economic prosperity.

Socialist Cuba survived thanks to massive aid from the Soviet Union, which sought to gain a foothold off the coast of the United States. The collapse of the USSR and the end of support in the 1990s triggered a deep economic crisis on the island, causing shortages of fuel, electricity, food, and basic goods. Amid widespread poverty and malnutrition, the authorities were forced to introduce ration cards. Eventually, Cuba managed to restore relative social stability, albeit at the cost of tightening control over the population.

The Castro regime was rescued by the rise to power in Venezuela of Hugo Chávez, who also sought to build socialism. Havane received cheap oil from its ally in exchange for sending tens of thousands of doctors and military personnel. However, this did not resolve Cuba’s fundamental problems, and its economy remained just as inefficient.

A quarter-century of socialist rule in Venezuela has led to equally dismal economic results, yet both countries have remained in a state of tense confrontation with the United States — a situation that sharply escalated after Trump returned to power determined to put an end to ideologically hostile regimes in his backyard. It appears he may be succeeding.

“Cubazuela”

The revival by the Trump administration of the Monroe Doctrine — which in the 19th century declared the entire Western Hemisphere a sphere of U.S. influence — marked a sharp turn not only in American foreign policy but in global politics. Dubbed the “Donroe Doctrine” (after Trump) in the 21st century, the new edition was quickly applied in the form of the operation to capture Nicolás Maduro on Jan. 3, 2026.

The very next day, speaking with journalists aboard his plane, Trump hinted at the possibility of the Cuban regime collapsing amid the halt in oil supplies from Venezuela. “I think it's just going to fall. I don't think we need any action,” the American president said.

Due to the lack of gasoline, cities in Cuba have stopped collecting garbage from the streets

The current U.S. Secretary of State, Marco Rubio — a descendant of anti-Castro Cuban emigrants — linked the overthrow of Maduro to the collapse of the regime on the island as early as 2019. In the Western Hemisphere, he said, the symbiosis of the two countries was called “Cubazuela,” with Cuba rumored to be receiving more than $1 billion a year from its neighbor in exchange for security and intelligence services. The announced deaths of Maduro’s 32 Cuban guards in the American raid became an important precedent, as it represented Cuba’s first inadvertent acknowledgment of its military presence in Venezuela.

Caracas reportedly covered one-third of Cuba’s oil needs, supplying an average of 30,000 barrels a day. The Americans claimed the figures were even higher: around 70,000 barrels of crude oil and petroleum products daily, totaling up to $1.3 billion from the end of 2024 until the start of the U.S. blockade in December 2025. Interestingly, Cuba sent more than half of the shipments — about 40,000 barrels — for resale in Asia.

At the time, the U.S. State Department considered the oil exports — which were made despite daily power outages on the island — to be a source of enrichment for the Cuban regime, as well as evidence of its corruption and incompetence. However, after the U.S. blockade of Venezuela’s coast began in the fall of 2025, the scheme gradually stopped generating profit.

Many of the ships transporting oil from Venezuela to Cuba were part of the so-called “shadow fleet,” traveling with their transponders switched off and falsifying location signals to avoid detection. According to some reports, part of the oil intended for Cuba was essentially smuggled out of Venezuela, with shipments not recorded in the documents of the Venezuelan oil company PDVSA.

Another important source of income for Cuba was the export of healthcare services (even though, yet again, such services were not always available to Cubans themselves). The “Oil for Doctors” program allowed Maduro’s predecessor Hugo Chávez to provide free medical care to millions of poor Venezuelans, thereby bolstering support for his regime. Chávez himself, after being diagnosed with cancer, spent his final months in Cuban hospitals.

However, Venezuela’s role in Cuba’s survival over the past three decades was perhaps even more decisive. The halt in Venezuelan oil supplies following the U.S. operation undermined Cuba’s already struggling economy.

Surviving on 13 USD a month

Cuba’s GDP per capita in 2024 was $7,381.4 — just over half (58%) of the global average. The average salary in 2025 reached 6,506 pesos per month — about $270 at the official exchange rate of 24 pesos per $1 set by the Cuban authorities. However, in February the U.S. dollar rate rose to 500 pesos on the black market, a record low for the national currency. By that measure, the average Cuban salary amounted to $13 per month. Current data suggest that 89% of Cuban families live in abject poverty, and 78% of Cubans want to leave the country or know someone who does. Remittances and parcels from relatives who emigrated to the United States are an important source of income for many locals. Each year, emigrants send about $2 billion in money and roughly the same amount in goods. According to a 2023 study by economist Emilio Morales, over the past 30 years, more than $100 billion was brought into Cuba this way.

Since the start of the new U.S. blockade, Cuba has plunged into perhaps the deepest crisis in its post-revolutionary history. Many schools have suspended classes, sending staff on unpaid leave. As the island has no fuel for planes, air travel has been suspended too, causing tourist hotels to pause operations. Piles of garbage line the streets, as collection has stopped due to the lack of gasoline. Food security has also been a challenge, as supplier companies cannot store perishable goods in refrigerators due to daily power outages.

Popular discontent is on the rise too. In January, the Cuban Observatory of Conflicts recorded a total of 953 cases of protests, complaints, and criticism of the authorities. In 395 cases, the actions were directed against the regime. These include nighttime “cacerolazo” protests (which involve banging on metal pots), graffiti and posters, arson attacks on propaganda billboards, but above all — numerous live streams and posts on social media, appeals to international and independent media, and hundreds of comments criticizing the Cuban leadership as a whole, rather than addressing “individual shortcomings.”

A “Viva Trump” sign on the Havana waterfront

In response, on Jan. 17 the National Defense Council of Cuba approved measures to prepare the country for a potential declaration of martial law. The regime’s leadership has begun appearing in public in military uniform and speaks more frequently about confronting Washington.

Cuban President Miguel Díaz-Canel called on Cubans to “resist creatively” by adopting a wartime mentality: “We are going to change the concept of the consumer basket. We will eat everything that is produced locally. If there is not enough fuel, food will not be able to move from one municipality to another.”

Venezuela distances itself

Díaz-Canel also reported on his telephone conversation with Delcy Rodríguez, Venezuela’s interim president, condemning U.S. military aggression and the kidnapping of Maduro but saying nothing about oil supplies or the future of the thousands of Cuban doctors and military personnel in Venezuela. Rodríguez, in purely rhetorical terms, thanked the Cuban president for his condolences to the Venezuelan people and those who died on Jan. 3.

Social media users noted that the formal nature of this conversation reflects the uncertainty of future relations between the two countries. Cuba has reasons to doubt that Rodríguez, who now claims friendship with Trump, makes independent decisions about her course of action.

On Feb. 21, Reuters reported that Cuban military personnel and doctors had begun leaving Venezuela. Rodríguez also swapped out her Cuban guards in favor of Venezuelan ones — most likely due to pressure from the Cuban authorities.

Cuban doctors and military personnel are leaving Venezuela

While Trump offered Havana a deal, the Cuban leadership claims that no negotiations are taking place. Since Washington has not disclosed its plans for the island, speculation about the likely course of developing events is widespread among experts and journalists. One of the most extreme scenarios would involve a total blockade of Cuba, which would quickly lead to a humanitarian catastrophe and a mass exodus of Cubans to neighboring countries, including to close U.S. partners like Panama, Costa Rica, and the Dominican Republic.

Several countries are already providing humanitarian aid to Cuba. China announced plans to supply 60,000 tons of rice and $80 million in financial assistance. The U.S. also pledged $6 million in humanitarian aid, which is insignificant compared to the scale of the disaster. The United Nations has traditionally expressed concern about the crisis in Cuba, but rapid assistance from the organization is unlikely, as in the fall of 2025 it had already allocated $74 million for the country’s recovery after Hurricane Melissa and to help 2.2 million people affected by the destruction.

On Feb. 15, Russia’s ambassador to Havana, Viktor Koronelli, stated that Moscow would soon begin supplying Cuba with humanitarian aid in the form of oil and petroleum products. On Feb. 18, Cuban Foreign Minister Bruno Rodríguez Parrilla met with Russian Foreign Minister Sergey Lavrov, and later with Vladimir Putin. Putin’s press secretary, Dmitry Peskov, commented on the meeting in brief, saying that “a range of specific issues were discussed.” In other words, the question of possible Russian oil supplies to Cuba remains open.

Trump on the war path

There are two answers to the question of who is to blame for the dire situation of Cuba’s people: either it is the communist regime, or it is the U.S. blockade. In Latin American and Spanish-language media, these polar positions often clash, with commentators unable to find any common ground.

After all, while it was not the United States that brought the Cuban economy to such ruin, America actively contributed to its degradation. Washington imposed its first sanctions on Cuba back in 1960, after Castro’s victorious barbudos began seizing the property of American companies following the revolution’s victory. In 1962, President John F. Kennedy tightened the restrictions to the level of an almost complete trade embargo, which has endured to become the longest in modern history. According to a 2016 report by the Cuban government, the embargo cost the island approximately $754.7 billion.

In past decades, the United States alternated between slightly easing restrictions before tightening them again. Trump, however, amped them up to the maximum.

In order to “counter threats from the Cuban government,” he signed an executive order on Jan. 29 imposing tariffs on any goods from countries that sell or supply oil to the island. As a result, Mexican President Claudia Sheinbaum suspended fuel supplies to Havana, thereby curbing the main source of fuel for the island since Maduro’s overthrow.

Sheinbaum emphasized that Mexico will continue providing humanitarian aid to Cuba, but this does not solve Havana’s problems. Nor does the U.S. authorization in early March for small shipments of Venezuelan oil. The Cuban authorities extended the notice of critical shortages of aviation fuel at all international airports in the country at least until April 10.

While increasing economic pressure on Cuba, the White House does not rule out negotiations based on the “Venezuelan model.” The Trump administration is looking for figures close to the Cuban government who could assist in toppling the communist regime, but whether Cuba has a sufficiently influential figure willing to cooperate with Washington remains to be seen.

Then there is the fact that, despite Maduro’s ouster, his regime in Caracas remains almost entirely intact — this despite the fact that Venezuelan society actually contains a legitimate opposition movement. In Cuba, on the other hand, the Communist Party has been the only political force for over 60 years and has formed a highly cohesive leadership, meaning real regime change there is even less likely. Even the Cuban diaspora in the U.S. pins its hopes of future reforms on a hypothetical member of the Communist Party or softening the system after coming to power.

Other measures to pressure Havana are also being taken. On Feb. 13, four U.S. Congresspeople of Cuban descent officially appealed to Trump to bring charges against former President Raúl Castro over the deaths of four people (including three Americans) killed in a Cuban Air Force attack on civilian aircraft on Feb. 24, 1996.

On that day, two planes from the organization “Hermanos al Rescate” (Brothers to the Rescue) were shot down while attempting to rescue Cubans who were trying to reach the U.S. on rafts. The attack took place in international waters, and Raúl Castro, who held the post of defense minister, was identified as the commander who gave the order to carry out the operation.

It is unclear how much time the Department of Justice will need to prepare an official indictment and present it in court. Raúl Castro is 94 years old making timing a critical factor in this case.

Hopes for a deal

One of the most controversial points in Trump’s Cuba plan is the possibility that members of the Castro family might remain on the island, escaping both exile and trial. Trump and Secretary of State Rubio appear to be ready to negotiate even with historical opponents if it helps achieve a regime change.

In early February, reports emerged that Alejandro Castro, Fidel’s nephew and Raúl’s son, had unofficially held talks with the CIA in which the parties discussed possibility of Havana’s consent to a “transition period” away from the Castro regime in exchange for U.S. economic concessions and cooperation in security — in other words, the Venezuelan model. The Cuban government denies that such negotiations took place.

Alejandro Castro Espín, nicknamed “One-Eye” (due, in fact, to the loss of an eye), is Raúl Castro’s only son. He played an important role in warming relations between the U.S. and Cuba in 2014 during the presidency of Barack Obama.

Alejandro Castro led Cuban intelligence for many years and was his father’s chief adviser. He then withdrew from the spotlight due to suspicions of involvement in organizing acoustic attacks on Western diplomats in 2018. The attacks were linked to Russian intelligence, with which Castro had collaborated closely. After a period of political isolation, in 2024 he began appearing in public again. His political authority and advanced negotiation skills make Castro a valuable participant in any transitional process in Cuba.

Alejandro Castro Espín, Raúl Castro’s son, offers condolences after Fidel’s death to his cousin Antonio Castro Soto del Valle, Fidel Castro’s son, at the Plaza de la Revolución in Havana on November 28, 2016.

On Feb. 18, Axios reported — citing three sources in the U.S. government — on secret negotiations between Marco Rubio and Raúl Guillermo Rodríguez Castro, Raúl Castro’s grandson and temporary guardian, bypassing the official channels of the Cuban leadership. This could also be disinformation, and the outlet's report about alleged negotiations with the Iranian leadership was, similarly, immediately denied in Iran. In any case, the Trump administration considers Raúl Castro a decision-maker in Cuba, and Rubio sees the old revolutionary’s 41-year-old grandson as a representative of the younger generation of Cubans, oriented toward business rather than communist ideals, and therefore ready to engage with Washington.

The U.S. decision to leave Maduro’s allies in power may have signaled to the Cuban leadership that Trump and Rubio are willing to make deals with ideological opponents. It is also significant for Americans that the younger Raúl Castro is closely connected to the leadership of the military-industrial conglomerate GAESA, which dominates the most important sectors of Cuba’s economy: tourism, trade, and the financial system. GAESA’s total profit is 3.2 times the island’s annual state budget revenue.

Raúl Castro and his grandson Raúl Guillermo Rodríguez Castro

The White House continues to exert political and economic pressure on Cuba, trying to prevent the conflict from escalating into armed confrontation. The example of Venezuela shows that after a months-long siege, the situation can suddenly resolve most unexpectedly. Turning Cuba into a U.S. ally will be much more difficult than the process was in Venezuela, with its more advanced economy and more developed political opposition. Nevertheless, the Venezuelan model of opening the economy without an actual change of power is possible on the island— in fact, the likelihood of the Cuban regime surviving for much longer as a U.S. adversary is much lower.