President Donald Trump saw the overthrow of Nicolás Maduro of Venezuela as a quick and clean operation that could not have gone better. On the other side of the world, in Iran, what he expected to be another fast-paced campaign turned into something much more complicated.
Closer to home, a third country is in Trump’s sights: Cuba. And while the country may fear a military invasion, the latest evidence suggests that Trump is considering a third way. On Friday, Cuba confirmed that its government is talking to US officials.
Trump, who overthrew Maduro in an operation carried out in January that lasted just a few hours, has left markets and allies in doubt about the next steps of his regime change plans for the island located 90 miles, or 145 kilometers, off the coast of Florida, whose communist leaders have resisted US pressure for decades.
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People familiar with the matter say Trump does have a plan. He wants to use American economic pressure to make the island financially dependent on Washington. The United States would, in practice, take the place of an old rival, the Soviet Union, which supported Cuba before its collapse in 1991.
“Cuba is going to fall very soon,” Trump told CNN last week. “Cuba is ready, after 50 years.”
Facing mounting pressure, the government in Havana promised to release dozens of prisoners late Thursday night. He also stated that Cuban President Miguel Díaz-Canel would speak to the press early Friday morning.
Speculation about a possible military overthrow of Cuba’s communist regime has circulated in Washington as U.S. attacks on Iran continue, fueled in part by statements from allies such as Senator Lindsey Graham, who told Fox News this week that “Iran is going to fall, and Cuba is next.”
But people familiar with Trump’s vision, who requested anonymity when discussing private deliberations, say that is not the preferred option. Instead, Trump sees Venezuela as a model, but in a different way.
After removing Maduro, the US began to support the more Washington-aligned administration of President Delcy Rodríguez, previously Maduro’s main ally.
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In Cuba, Trump and top allies want to replace Díaz-Canel, whom they blame for leading the economy to collapse and consider incapable of leading the necessary political and economic changes, according to one of the people.
American officials held talks with Raúl Guillermo Rodríguez Castro, grandson of Raúl Castro, former president of Cuba and brother of the late Fidel Castro.
A colonel in Cuba’s Interior Ministry, the younger Castro has strong family ties to the military conglomerate that controls large parts of the Cuban economy.
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Trump and senior US officials, including Secretary of State Marco Rubio, have tightened the economic clampdown on Cuba since January, when the United States announced a quarantine on oil destined for the government. The president used the threat of tariffs to convince Mexico, the island’s last major oil supplier after Maduro’s removal, to halt shipments.
The U.S. now regulates the flow of energy into the country by allowing companies to sell fuel to its tiny but rapidly growing small and medium-sized business sector, but not to the government.
Reached for comment on Thursday night, the Cuban embassy in Washington referred to statements on Facebook by Deputy Foreign Minister Carlos Fernández de Cossío, in which he called the American quarantine on government energy imports “an ongoing form of collective punishment.”
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“The possibility of conditional sales to the private sector already existed and does not alleviate the impact on the population,” he said.
Díaz-Canel stated that he is willing to negotiate with the US, but on equal terms. He also warned that the country is strengthening its military defenses.
The focus on a high-ranking official close to the current regime follows the contours of Trump’s incursion into Venezuela, during which American forces removed Maduro but left Rodríguez, his vice president, in command. Contrary to what happened in Iran, Trump managed to change the face of the government, and its stance towards Washington, without losses of American troops, even though dozens of Cuban and Venezuelan soldiers and intelligence agents died protecting Maduro.
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The US is now seeking to attract billions of dollars in investment to open Venezuela’s state-controlled economy to American companies, especially in the oil and mining sectors. And although Rodríguez has publicly maintained the socialist ideology that marked the governments of Maduro and the late Hugo Chávez, Trump praised her for cooperating with the US.
Cuba also presents challenges that Venezuela did not. For six decades, the communist regime banned opposition political parties, leaving a vacuum of potential leaders capable of ushering in the kind of return to democracy that the United States says will eventually occur in Caracas.
Attracting investment into the Cuban economy would likely be even more difficult than it has been in Venezuela, as Cuba does not have comparable reserves of oil and natural resources to develop.
Still, Havana could offer Trump a chance to succeed as the war in Iran drags on, even if he doesn’t deliver the complete overthrow of the Castro regime long sought by Rubio and others in the US.
Like Rodríguez, the younger Castro is seen by the Trump administration as a potentially pragmatic leader who could be encouraged to reach deals free from the orthodoxy of the revolution led by Fidel and Raúl Castro, the source said.
Florida Republican Representative Mario Díaz-Balart, a longtime ally of Rubio and whose parents, like Rubio’s, emigrated to the US from Cuba, confirmed in an interview with CBS this week that there are ongoing conversations with people “around” Raúl Castro. Díaz-Balart predicted that the current regime will not survive Trump’s term, which runs until January 2029.
The White House declined to comment, pointing to recent statements by Trump. At a summit of Latin American leaders in Doral, Florida, last weekend, he said Cuba is “in its last moments of living as it was.” He added that the “focus now is on Iran,” but that after that, Rubio will take “an hour off and then conclude a deal on Cuba.”
The administration does not appear to be planning a military strike against Cuba, but rather a negotiated transition of government, said Kimberly Breier, who was assistant secretary of State for Western Hemisphere Affairs in Trump’s first term.
“The predominant factor in both Venezuela and Cuba is stability,” said Breier, now a senior advisor at strategic consultancy Torridon Group in Washington. “The government wants change, but it doesn’t want it to be chaotic, cause mass migration or create more space for adversaries. It’s a more gradual approach, based on stability.”
The Navy has previously helped the U.S. Coast Guard intercept ships carrying sanctioned Venezuelan oil, which in recent years often had Cuba as its destination. And for Cuba’s patrons over the centuries, from Spain to the US under then-president William McKinley, one of Trump’s political idols, to the Soviet Union, control has included at least some display of military might.
Meanwhile, the island’s economy is on the brink of collapse. Decades of communist rule, along with the US trade embargo, have impoverished Cuba and stifled growth. The country now faces a humanitarian crisis, and the State Department has sent $9 million in aid through the Catholic Church to bypass the government.
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