After Venezuela and Greenland, Why Trump's Next Focus Could Be Cuba

Emboldened by the US success in ousting Venezuelan President Nicolas Maduro and his continued push to annex Greenland, US President Donald Trump is now reportedly seeking regime change in Cuba. The Trump administration is actively searching for Cuban government insiders who can help cut a deal to push out the Communist regime by the end of the year, according to a report by The Wall Street Journal. 

The Trump administration does not have a "concrete plan" for doing away with the Communist government that has held on to power in the Caribbean island for almost seven decades, according to the outlet, but President Miguel Diaz-Canel's grip on the island has never been more fragile. 

In the wake of its benefactor and ally, Venezuelan dictator Maduro's ouster, Cuba's economy is on the brink of collapse, the outlet reported, citing US officials.

Cuba-Venezuela Nexus

Cuba has long been an ally of Venezuela's socialist regime, providing medical, security and intelligence personnel in exchange for subsidised oil. Nearly three dozen Cuban agents guarding Maduro were killed during the US mission, and their bodies were repatriated to the island last week during a ceremony attended by 94-year-old former President Raul Castro and current President Miguel Diaz-Canel.

Now, US intelligence assessments reportedly indicate that Cuba is facing chronic shortages of basic goods and medicines and is suffering from frequent blackouts. The island nation is likely to run out of fuel within weeks, bringing the economy to a grinding halt, with the Trump administration aiming to prevent any more Venezuelan oil from flowing to Cuba to weaken the regime further. 

According to the report, Team Trump is also aiming for Cuba's overseas medical missions, Havana's most important source of hard currency, including through visa bans targeting Cuban and foreign officials accused of facilitating the programme.

But, despite a deepening economic and humanitarian crisis marked by shortages of food, fuel and medicine, Cuba continues to maintain close ties with US adversaries such as Russia and Iran – relationships that have heightened concern in Washington.

US plan

Maduro's capture by US forces and its subsequent success in getting concessions from the interim Venezuelan government is reportedly being seen by the Trump administration as a blueprint for Cuba. For that, US officials told The Wall Street Journal that during meetings with Cuban exiles and civic groups in Miami and Washington, they have focused on identifying somebody inside the current government who will cut a deal with the US.

The January 3 raid to capture Maduro also, an asset within the Venezuelan leader's inner circle, reportedly helped the US forces.

While the US hasn't publicly threatened to use military force in Cuba, Trump has said, "I strongly suggest they make a deal BEFORE IT IS TOO LATE".

"NO MORE OIL OR MONEY" would be going to Cuba, the US leader stated in a January 11 Truth Social post. 

US officials also reportedly said that the brazen raid that extracted Maduro should serve as an implicit threat to Havana.

"The Cuban government has a choice," Jeremy Lewin, a State Department official for foreign assistance and humanitarian affairs, told reporters last week. If Havana continues repression and steals from recent shipments of US aid, the country will be held accountable, he said.

"What's going on in Venezuela should make clear to the Cuban regime and every other despot around the world that you don't play games with President Trump," Lewin said. "Weakness and disorder, strife and foreign interference in our hemisphere are done."

The US State Department has said that it is in America's national security interests for Cuba "to be competently run by a democratic government and to refuse to host our adversaries' military and intelligence services."

The Trump administration plans to ratchet up the pressure on Cuba while simultaneously negotiating "an off-ramp" for the country's leaders, namely 94-year-old Raul Castro, the brother of deceased long-time dictator Fidel Castro, and Cuban President Miguel Diaz-Canel.

Cuba's Stance

Cuban Deputy Foreign Minister Carlos Fernandez de Cossio called "apocalyptic threats against Cuba" from the State Department "clear miscalculations" in a post on X. 

The State Department announced Wednesday that it was sending $3 million in "much-needed disaster relief to the Cuban people affected by Hurricane Melissa." The shipments, which included food, water treatment kits, kitchen equipment, blankets and solar lanterns, were sent from Miami to the eastern cities of Holguin and Santiago de Cuba.

Foreign Minister Bruno Rodriguez said in a post on X that while the Cuban government was open to receiving such assistance in principle, the US was taking advantage of a humanitarian issue "for opportunistic and political manipulation purposes."

Cuba and the US became adversaries after the Castro brothers descended from the country's Sierra Maestra mountains with a bearded crew of guerrillas in 1959. The communist regime in Havana has withstood years of intense US pressure, from the Central Intelligence Agency-backed Bay of Pigs invasion in 1961 to a punishing embargo imposed in 1962 that became more stringent over time.

Difficulties In US Plans

Many US allies want an end to Communist rule in Cuba. But the ouster of the cash-strapped government could push Havana towards the kind of turbulence and humanitarian crisis that Trump was eager to avoid in Venezuela, where he opted to keep top loyalists in place.

The leaves Team Trump short of a clear plan for what to do next and who could replace the current regime, the report said.

The Venezuela model is hard to replicate in Cuba, which is a single-party Stalinist state that bans political opposition. Unlike Venezuela, which has an opposition movement, frequent protests and elections, civil society barely exists in Cuba.

"These guys are a much tougher nut to crack," said Ricardo Zuniga, a former Obama administration official who helped negotiate the short-lived détente between the US and Cuba from 2014 to 2017. "There's nobody who would be tempted to work on the US side."

Over the last 7 decades, the Cuban regime has never been willing to negotiate regarding changes to its political system, and only implemented fitful and minor economic changes.

Trump believes that ending the Castro era would cement his legacy and do what President John F Kennedy failed to do in the 1960s.