The Unfree Island: how pressure from Trump could push Cuba's communist regime to the brink

Following the United States' operation to arrest Nicolás Maduro, Donald Trump has expanded his threats beyond Venezuela to Greenland, protest-hit Iran, Colombia and Mexico. Cuba's communist regime is now also in the firing line. What is behind this broader push?
Cuba is affected by Maduro's capture and transfer to the United States more than any other Latin American country except Venezuela itself.
Caracas and Havana, bound by a shared state-socialist model, began deepening their ties after a landmark meeting in 1999 between Hugo Chávez, the late mentor and predecessor of Nicolás Maduro, and Fidel Castro, the architect of the Cuban Revolution. Venezuela shipped oil to the communist‑run unfree island and Cuba reciprocated by sending doctors and, in due course, military personnel to Venezuela.
After Chávez's death, it was Maduro, shaped by political training in Cuba, who took the reins. He had been earmarked for the role, in part because he suited the Castro brothers. Maduro has now been ousted and is set to face narco‑terrorism charges in a US court.
Cuba's prospects look bleak as the United States has stepped up efforts to intercept and seize tankers carrying sanctioned Venezuelan oil and signalled plans to take control of Caracas's crude exports.
Trump has warned that Cuba will no longer receive a single barrel of oil from Caracas and has demanded that Venezuela's acting president, Delcy Rodríguez, cut all economic ties with Havana.
For Cuba's crisis-hit economy, plagued by constant blackouts, poor sanitation and a growing exodus to the United States, losing these energy resources could be devastating. Aid from a country bordering the US, however, could offer partial relief.
Learn the current state of Cuba's economy, who is pushing Trump to use oil as a tool of pressure on the island and which country is actively supplying Havana with oil.
Threats from Trump and the Rubio factor
After the special operation against Maduro, the White House declared: "We live in a world, in the real world … that is governed by strength, that is governed by force, that is governed by power. We're a superpower. And under President Trump, we are going to conduct ourselves as a superpower." The US State Department further spelt out Washington's claims to the entire Western Hemisphere: "This is OUR Hemisphere, and President Trump will not allow our security to be threatened."
Against this backdrop, Cuba, along with Iran, Greenland, Colombia and Mexico (over what the US calls drug‑trafficking issues), was immediately flagged as a potential next target for Trump. The island nation, just 145km south of Florida, has been under a US trade embargo since the early 1960s, following Fidel Castro's Cuban Revolution.

Venezuela, home to the world's largest oil reserves, has long supplied Cuba with fuel – up to 35,000 barrels per day – in exchange for doctors and support for Maduro's military and security forces. Now, with Washington announcing that it will "indefinitely" control Venezuelan oil exports, Havana, already grappling with a deepening economic crisis, is at risk of falling into an even harsher situation.

Trump has on several occasions hinted at this scenario. He initially suggested that, unlike in Venezuela, military intervention might not be necessary for Cuba, saying "It's going down. It's going down for the count."
Since then, the US president has issued a fresh warning to Havana, declaring that it would no longer receive Venezuelan oil. "THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA – ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE", he emphasised, without specifying what type of deal he had in mind.
Cuban President Miguel Díaz-Canel, who succeeded Raúl Castro in 2018, responded: "Unlike the US, we do not have a government that engages in mercenary practices, blackmail, or military coercion against other States. Like every country, Cuba has the absolute right to import fuel from those markets willing to export, which exercise their own right to develop their trade relations without interference or subordination to the unilateral coercive measures of the United States. Cuba is a free, independent and sovereign nation. No one dictates to us what to do. Cuba does not attack; it has been attacked by the United States for 66 years. Cuba does not threaten; it prepares itself, willing to defend the Homeland to the last drop of blood."
Castro Jr., now 94, initially declined to run for a third presidential term and later stepped down as head of the Communist Party, but he has retained significant influence. Díaz-Canel has widely been seen as little more than an executor of the old guard's directives.

Overall, Trump and senior officials in his administration are adopting an increasingly aggressive stance towards Cuba. One of the chief proponents of pressure on the island's communist government is Secretary of State Marco Rubio, an American of Cuban descent and former governor of Florida, home to the largest Cuban diaspora community.
The New York Times reported that Rubio had spearheaded the campaign of political and military pressure on Maduro, which ultimately led to the Venezuelan leader's removal from power. Rubio has long argued that toppling Maduro's regime would deal a significant blow to Cuba's communist government.
Rubio, son of Cuban immigrants, aims to be the architect – working under Trump – of bringing an end to 60 years of communist rule in his parents' homeland.
After Fidel Castro's 1959 revolution, the US imposed a trade embargo in response to the nationalisation of American-owned property. Under the embargo, coupled with government mismanagement, Cuba has plunged into deep economic and energy crises, driving many Cubans to flee, mostly to the United States.
"Venezuela has become the operating hub for Iran, for Russia, for Hezbollah, for China. That's not going to exist," Rubio said, justifying the US intervention and declaring Latin America the US's "backyard", where Washington has the right to call the shots.
Rubio is poised to play a key role in Washington's future actions against Cuba, as the US embargo on the island that stretches beyond six decades has failed to topple the Castro brothers. Trump has even floated, half in jest, the idea of Rubio becoming Cuba's president.

Cuba's fragile economy
The White House's move to "indefinitely" control Venezuelan oil exports could leave Havana without its main ally. Already grappling with its worst economic crisis since the Cold War, Cuba has endured weeks of blackouts, shortages of food and medicine, mountains of uncollected trash, a squalid sanitary situation and ageing Soviet-era cars.

In recent weeks, Cuba has seen a surge in mosquito-borne diseases, with large numbers of people affected by dengue fever and chikungunya. Once hailed as the "pearl of the revolution," the Cuban healthcare system is struggling to cope.
The alliance between Havana and Caracas, which was forged by Castro and Chávez, encompasses military, political and economic cooperation. Although Cuba has consistently denied deploying security forces in Venezuela, Havana declared two days of mourning for the "32 brave soldiers" killed during the US operation targeting Maduro.
In a brief statement, Havana skirted around specifics regarding its forces. Díaz-Canel claimed that they had guarded Maduro and his wife "at Caracas's request", but international reporting has long shown that Cuba trades security support in Venezuela for oil.
The deaths of Cuban personnel in the US special operation laid bare their deep involvement in Venezuela's intelligence and armed forces. Maduro's security detail was made up almost entirely of Cuban guards.
"Except for a very small minority, no one in Cuba is rejoicing at the tragic events in Venezuela. There is a very strong attachment to sovereignty in Cuban society. The fear of losing an ally like Venezuela can only fuel anxiety among a population facing an unprecedented social crisis", said Janette Habel, a researcher at the Institute of Advanced Studies on Latin America specialising in Cuban affairs.
Habel said Cuba's economy started to unravel in 2016, coinciding with Venezuela's financial meltdown. At the time, Caracas accounted for nearly half of Havana's trade, mostly oil, but by 2025 that share had dropped to just 10%. The COVID‑19 pandemic and new sanctions imposed by Trump during his first term further limited Cuba's trade and financial ties with the rest of the world.

In this context, Trump's hardline demand that Venezuela cut all economic ties with Havana has alarmed many on the island, who now fear blackouts will become even more frequent.
For years, Venezuela supplied oil to Cuba in exchange for medical services: Cuban doctors sent overseas generated nearly €10 billion in export revenue in 2014 – a figure that had halved by 2022. The coronavirus pandemic slashed tourism revenues threefold, while the sugar sector, long considered the backbone of Cuba's agro-industry, has collapsed entirely over these years.
Amid constant blackouts, soaring inflation of up to 500% and medicine shortages at the height of the pandemic, large-scale anti-government protests erupted in July 2021. The regime crushed them swiftly, handing prison sentences to more than 700 people. Later demonstrations were smaller and generally stopped short of calling for the government's overthrow, but, in the words of Carolina Barrera, a Cuban activist in exile, fear began to recede.
Habel said: "The regime's loss of legitimacy is undeniable, and this concerns Raul Castro [Fidel Castro's brother, president from 2008 to 2018 and now an MP] first and foremost, who initiated, starting in 2011, a market-oriented reform but maintained authoritarian rule, following the Vietnamese model."

Facing a severe financial crunch, Cuba resold part of Venezuela's oil to China, worsening the island's energy shortage even before Maduro's arrest. Yet experts caution that the system is far from collapsing. Stephen Wilkinson of Buckingham University says Cuba is in a "challenging economic situation", but stresses it is not yet critical.
Wilkinson notes that Cubans have grown accustomed due to years of severe shortages. Fuel scarcities could weaken the military, but any invasion attempt would face determined resistance from the population.
The expert adds that despite Trump's threats, Cuba still has other revenue streams beyond Venezuelan oil, notably tourism, medical service exports and nickel, a resource whose value is rising thanks to its use in the AI sector.
A lifeline from Mexico and potential scenarios
For years, Cuba's regime has relied on a handful of key patrons, chiefly Russia and China, which use the island as a geopolitical foothold to counterbalance the United States.
Havana, like Tehran and Caracas, has now found itself without meaningful backing from the Kremlin at a critical moment. "As President Vladimir Putin focuses his attentions on Russia's war in Ukraine, his strategic allies around the world have been left feeling neglected – or worse," Bloomberg notes. [N.B. Ukrainska Pravda does not recognise Putin as president – ed.]
Critically important fuel exports from Venezuela stopped about a month ago following a US naval blockade of Caracas. The last tanker carrying oil to Cuba sailed in mid-December, according to shipping data and internal documents from state oil company PDVSA.

However, Cuba will not be left completely without oil – Mexico has stepped in. "Surprisingly, there is no sign of panic from the Cuban state: either because Mexico has assured them they would receive oil, or because China could help further develop their solar energy network, which is becoming significant," Habel noted.
Following developments in Venezuela, Mexican President Claudia Sheinbaum confirmed that the shifting regional landscape does indeed position Mexico as a "significant supplier" of oil to Cuba.
"Mexico has long sent oil to Cuba. We have a contract with them, and this is also a humanitarian gesture toward the Cuban people. Mexico has always opposed the [US] embargo, established in 1962, because of its harmful impact on the population," she explained. However, she stressed that "no more oil is being sent than has been sent historically".
Sheinbaum was commenting on a Financial Times article warning that Mexico risks Donald Trump's ire with its Cuban oil shipments, which alarmed many in the country, given the US president's threats against Havana and Mexico City. The FT, citing data from analytics platform Kpler, reported that it was Mexico that had overtaken Venezuela as Cuba's main oil supplier last year.
Kpler estimates indicate that in 2025, Mexico supplied nearly 44% of Cuba's oil imports, while Venezuela provided 34%. Russia contributed around 15% and Algeria another 6%.
Official data from Mexican state-owned Petróleos Mexicanos show that from January to 30 September 2025, Mexico supplied Cuba with 17,200 barrels of crude oil and 2,000 barrels of petroleum products per day. By comparison, Maduro's government exported an average of 35,000 barrels of oil and petroleum products per day to Cuba in the preceding three months.
Mexico's oil shipments have already drawn criticism from Trump allies. "Mexico continues to finance the tyranny, sending resources to a criminal regime while the Cuban people suffer hunger and repression. This hemisphere does not need neutrality. Neutrality is complicity. Mexico is too large and too important to serve as a lifeline to dictators in Havana and Caracas," said Republican Congresswoman Maria Elvira Salazar of Florida.

Despite the criticism and Trump's own call for "zero barrels for Cuba", US Energy Secretary Chris Wright later confirmed that Washington's current strategy allows Mexico to keep supplying oil to the island.
Sources told CBS News that Trump is not actively trying to topple Cuba's regime, but aims to negotiate a peaceful transition away from the island's authoritarian communist system. President Miguel Díaz-Canel, however, has denied that any such talks with Washington are underway.
US officials also warn that a full stop to oil supplies would further strain Havana's ageing, overburdened power grid, which already struggles with constant blackouts.
Could Cuba turn to other oil suppliers beyond Mexico? Paul Webster, former UK ambassador to Cuba, suggests that, in theory, Havana could seek support from other friendly regional powers, specifically Brazil and Colombia.
Webster said Cuban communism, having survived the collapse of the USSR, could also endure Venezuela's fall. He noted that Havana's leadership watches as other countries' leaders find common ground with Trump through dialogue, flattery and mutual-benefit deals, and added that nothing prevents Cuba from seeking a similar agreement, especially since diplomatic relations restored under Obama and Raúl Castro remain intact.

Wilkinson stresses that even in Venezuela, where opposition parties still operate, there is no serious talk of regime change. That makes it even harder to imagine such a scenario in Cuba, where the Communist Party has been the country's only permitted political force for more than 60 years.
The analyst said there is no alternative force in Cuba capable of taking power and described the Cuban leadership as "extremely united".
He added, however, that this does not rule out the emergence of potential reformers within the Communist Party, noting that many in Miami and the Cuban-American community view the most likely scenario as one in which a figure from the party or the army positions themselves as a reformist technocrat.
Author: Oleksii Pavlysh
Translation: Artem Yakymyshyn
Editing: Shoël Stadlen
