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Home»News»INTERNATIONAL»How Far Will Trump Push Cuba? By Christopher Sabatini
INTERNATIONAL

How Far Will Trump Push Cuba? By Christopher Sabatini

National RecordBy National RecordFebruary 19, 2026Updated:February 19, 2026No Comments7 Mins Read
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Vehicles wait in line to refuel at a gas station in Havana on 30 January 2026.
Vehicles wait in line to refuel at a gas station in Havana on 30 January 2026. (Photo by Adalberto ROQUE/AFP via Getty Images)
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THE US’s 64-year embargo on Cuba is about to get a lot tougher. The Trump administration has cut off the estimated 27,000 to 35,000-barrel-per-day deliveries of cheap Venezuelan oil to the island and is threatening tariffs on countries that may think about trying to fill the void. 

The end of that oil lifeline comes as Cuba is already suffering its worst economic crisis since the 1959 revolution – one that has brought rolling electrical blackouts, declining hard currency reserves, and food and fuel shortages.

Unlike Venezuela’s chaotic and corrupt government, the Cuban state has seen sixty-plus years of uninterrupted rule under Fidel Castro and then his brother Raul, allowing the Communist party to dominate and remake government. 

President Donald Trump has said that he’s offered a deal to the Cuban government, headed by Miguel Díaz-Canel, and that the two governments are having discussions. The Communist Cuban regime faces an impossible choice: concede to White House demands that will threaten its power – for instance, to release political prisoners and hold elections – or try to use repression to cling on through a looming humanitarian crisis that could erupt into chaos and/or massive outmigration.  

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The decision will depend on what the Trump administration is offering. The US embargo – codified into law in the 1992 Cuban Democracy Act and again in the 1996 Cuban Liberty and Democratic Solidarity Act (Cuban Liberty Act) – places legal limits on what the US president can guarantee as concessions. The US’s politically powerful, majority Republican, Cuban-American community will also have a say. 

All this also comes with a reminder, if not a warning: Cuba is not Venezuela. As much as Trump may feel emboldened by his 3 January intervention that removed President Nicolas Maduro and his wife, leaving his regime and cabinet in place, the factors in play in Cuba present a quite different challenge to the ‘Donroe Doctrine’.

Cuba does not sit atop vast oil reserves and has no untapped mineral riches. There is no great economic win offered to the US by a change of government. Even the sugar industry that built pre-revolution Cuba has collapsed. Nor, despite its close relations with Russia, China and Iran, does Cuba represent a national security threat.  

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Instead, this is largely driven by ideology, the hangover of the Cold War in which 66 years and 13 US presidents have failed to topple the stated nemesis 90 miles off the coast of Florida.

Cuban factors

Unlike Venezuela’s chaotic and corrupt government, the Cuban state has seen sixty-plus years of uninterrupted rule under Fidel Castro and then his brother Raul, allowing the Communist party to dominate and remake government. 

Public officials and the Revolutionary Armed Forces (FAR) of Cuba have been indoctrinated in the myth of the revolution and fear change. And the FAR’s ownership of key areas of the economy – including tourism and financial services integrated under large holding companies – helps ensure their loyalty.  

Within the regime, it is uncertain exactly where power lies. Diaz Canel is a relatively young leader, at least compared to the ‘historicos’ that had governed the country since 1959. A party apparatchik, hand-picked by the ideologically bankrupt regime to replace 94-year-old Raul Castro in 2018, he finds himself in a difficult position.  

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The Castro legacy hangs over him, and while he still provides fiery anti-Yanqui rhetoric, empty state food stores shelves show that the revolution has run out of gas. 

Meanwhile, Raul Castro’s son Alejandro remains in power, occupying a vaguely defined role in the Interior Ministry. Allegedly, he has become the lead negotiator for the regime: Unconfirmed reports claim that he has been in dialogue with the US, though those claims have been questioned.

Domestic politics, proximity, the comparative coherence of the Cuban regime and the limits on what Donald Trump can offer in any potential deal mean that a game of chicken with the Cuban government could have a host of unintended consequences. Those consequences could potentially become more violent and politically fraught than those in Venezuela. In a country so close to the US, this is a very real risk of Trump’s pressure policy – and may anger his political base far more than Venezuela has.

Six decades of totalitarian control and repression has atomized Cuban society. There is no democratic leadership in waiting as there was in Venezuela that enjoys the popular legitimacy of an election. And Cuba’s small independent political and civil society remains divided and isolated internally.  

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Many of those who oppose the communist regime have left. Since the Revolution, between 2 to 3 million Cubans have escaped brutality and economic failure by fleeing to the United States, Spain and countries in Latin America (numbers vary widely because of the multiple exit methods and dispersion).  

The exodus has served as a convenient safety valve for the Cuban regime, removing the most disgruntled citizens from political and civic life on the island. It has also created a large and highly politically motivated political force in the US.

Washington’s aims

The large Cuban-American community has waited decades to return to the island. Many want to see the communist regime of former President Fidel Castro collapse and a transition to democracy like those in Eastern Europe in 1989 and the early 1990s. That presents a political risk for Trump.  

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There are legal limits on what his administration can offer Cuban citizens and the Cuban diaspora in any potential deal with the Cuban regime. The 1996 Liberty Act reconfirmed the US embargo as law. 

It also added a set of conditions that any future president would have to confirm had been met in order for the Congress to lift the embargo. Those conditions include: the removal of all Castros from government, the release of political prisoners, the return of freedoms of association and speech, and credible steps to multi-party elections.   

While President Trump was willing to buck Congressional oversight in his Venezuela adventure, doing so in this case could incur the wrath of embargo supporters, largely Republicans. 

Or perhaps it might not. Loyal Republican partisanship and faith that Trump can deliver change, even if not immediately, may maintain their support.

Regardless, Venezuela-style leadership change will not be sufficient under US law to re-establish meaningful economic relations. And any promises by the regime – with or without the current leadership – to eventually release political prisoners, loosen restrictions of basic freedoms and hold free and fair elections will be met with legitimate skepticism by democratic and human rights activists and non-partisan Cuban-Americans.

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The other scenario is even more problematic. More than a decade ago, a former Commander of US Southern Command told me the most immediate security risk is a popular uprising on the island that sparks adventurous Cuban-Americans to embark for Cuba to join the protestors and quicken the transition to democracy – triggering violence from the Cuban security forces. Should that affect US citizens in Cuba, pressure would build for US forces to intervene on the island to defend its citizens. That in turn could spark a broader conflict.

Domestic politics, proximity, the comparative coherence of the Cuban regime and the limits on what Donald Trump can offer in any potential deal mean that a game of chicken with the Cuban government could have a host of unintended consequences. Those consequences could potentially become more violent and politically fraught than those in Venezuela. In a country so close to the US, this is a very real risk of Trump’s pressure policy – and may anger his political base far more than Venezuela has.

Dr Sabatini is Senior Research Fellow for Latin America, US and North America Programme.

Culled from Chatham House website

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