Trump’s plan for Cuba would make the US the island’s patron

President Donald Trump saw his capture of Venezuela’s Nicolas Maduro as a quick, clean operation that could not have gone better. Half a world away in Iran, what he hoped would be another fast campaign has devolved into something far more complicated.

Close to home, a third country is in Mr Trump’s crosshairs: Cuba. And while the country may fear a military invasion, the latest indications suggest Mr Trump is considering a third way.

On March 13, Cuba confirmed its government is talking with US officials.

Mr Trump, who toppled Maduro in a January operation that lasted mere hours, has kept markets and allies alike guessing about the next steps in his regime change plans for the island 145km off the Florida coast whose Communist leaders have held out against US pressure for decades.

People familiar with the matter say Mr Trump does have a plan. He wants to use American economic pressure to make the island nation financially dependent on Washington.

The US would essentially take the place of its onetime rival, the Soviet Union, which kept Cuba afloat before it collapsed in 1991.

“Cuba is going to fall pretty soon,” Mr Trump told CNN last week. “Cuba’s ready – after 50 years.”

In the face of mounting pressure, the government in Havana vowed to free dozens of prisoners late on March 12. It also said Cuban President Miguel Diaz-Canel would speak to the press early on the morning of March 13.

Speculation about a possible military overthrow of Cuba’s Communist regime has swirled around Washington as US strikes in the Iran have continued, fuelled in part by talk from allies like Senator Lindsey Graham, who told Fox News this week that “Iran is going down, and Cuba is next”.

But the people familiar with Mr Trump’s thinking, who asked not to be identified discussing private deliberations, say that’s not a preferred option. Instead, Mr Trump sees Venezuela as a model in a different way.

After ousting Maduro, the US has backed the more US-friendly administration of President Delcy Rodriguez, once Maduro’s top lieutenant. 

In Cuba, Mr Trump and top allies want to replace Mr Diaz-Canel, whom they blame for running the economy into the ground and regard as incapable of overseeing necessary political and economic changes, according to one of the people. 

US officials have held talks with Raul Guillermo Rodriguez Castro, the grandson of Raul Castro – a former Cuban president and brother of the late Fidel Castro.

A colonel in Cuba’s interior ministry, the younger Castro holds deep family ties to the military conglomerate that controls large parts of the Cuban economy. 

Mr Trump and top US officials, including Secretary of State Marco Rubio, have tightened the economic screws on Cuba since January, when the US announced a quarantine on oil going to government. The president used tariff threats to convince Mexico, the last major oil supplier to the island after Maduro’s removal, to stop shipments. 

The US is now regulating the flow of energy to the nation by letting companies sell fuel to its minuscule but fast-growing sector of small- and medium-sized businesses – but not the government.

Asked for comment on the night of March 12, the Cuban embassy in Washington referred to comments on Facebook by Deputy Minister of Foreign Affairs Carlos Fernandez de Cossio, where he called the US quarantine of energy imports to the government “a form of collective punishment remains”.

“The possibility of conditional sales to the private sector already existed, and does not alleviate the impact on the population,” he said.

Mr Diaz-Canel has said he is willing to negotiate with the US, but as equals. He also has warned that the country is bolstering its military defenses.

The focus on a high-ranking official close to the current regime follows the contours of Mr Trump’s Venezuela incursion, during which US forces whisked away Maduro but left Ms Rodriguez, his vice-president, in charge.

Unlike in Iran, Mr Trump succeeded in changing the face of the government – and its approach to Washington – without the loss of US troops, even as dozens of Cuban and Venezuelan soldiers and intelligence agents died protecting Maduro.

The US is now seeking to attract billions of dollars in investment to open Venezuela’s state-controlled economy to American companies, particularly in the oil and mining sectors. And even as Ms Rodriguez has outwardly maintained the socialist ideology that defined the rule of Maduro and the late Hugo Chavez, Mr Trump has praised her for cooperating with the US.

Cuba also poses challenges that Venezuela did not. For six decades, the Communist regime has banned opposing political parties, leaving a vacuum of potential figures who could lead the sort of return to democracy that the US says will eventually take place in Caracas. 

Attracting investment to Cuba’s economy would likely prove even more difficult than it has in Venezuela, since Cuba lacks comparable oil and natural resources to develop. 

Still, Havana may offer Mr Trump a chance at success while war in Iran drags on, even if he does not deliver the full toppling of the Castro regime that Rubio and others in the US have long sought. 

Much like Ms Rodriguez, the younger Castro is seen by the Trump administration as a potentially practical leader who could be incentivized to cut deals free from the orthodoxy of the revolution that Fidel and Mr Raul Castro led, the person said.

Florida Republican Congressman Mario Diaz-Balart, a longtime Rubio ally whose parents, like Mr Rubio’s, immigrated to the US from Cuba, confirmed ongoing conversations with people “surrounding” Mr Raul Castro in an interview with CBS this week.

Mr Diaz-Balart predicted the current regime will fail to outlast Mr Trump’s presidency, which runs through January 2029.

The White House declined to comment, pointing to Mr Trump’s recent comments. At a summit of Latin American leaders in Doral, Florida last weekend, he said Cuba is “in its last moments of life as it was”.

He added that the “focus right now is on Iran,” but that after that, Mr Rubio will take “one hour off, and then he’ll finish up a deal on Cuba”.

The administration does not appear to be planning for a military strike against Cuba, but rather for a negotiated transition in government, said Ms Kimberly Breier, assistant secretary of state for Western Hemisphere Affairs during Mr Trump’s first term.

“The overriding factor in both Venezuela and Cuba is stability,” said Ms Breier, now a senior adviser at strategy firm Torridon Group in Washington.

“The administration wants change, but doesn’t want it to be chaotic, have it drive mass migration, generate more openings for adversaries. It’s more of a gradual, stability-based approach.”

Already, the Navy has helped the US Coast Guard interdict ships carrying sanctioned Venezuelan oil that in recent years often went to Cuba. And for Cuba’s patrons over the centuries, from Spain to the US under then-President William McKinley – one of Mr Trump’s political idols – to the Soviet Union, control included at least a flexing of military power.

The island’s economy, meanwhile, is teetering.

Decades of Communist rule, along with a US trade embargo, impoverished Cuba and choked off growth. It is now facing a humanitarian crisis, and the State Department has sent US$9 million (S$11.5 million) in aid through the Catholic Church to bypass the government. BLOOMBERG