Donald Trump's announcement of securing a "major deal" with Iran has reignited a pressing question regarding the Caribbean: Is Cuba next on his agenda?
On June 4, speaking from the Oval Office, Trump vowed to address the situation in Cuba once the Iranian front was concluded.
"I like to tackle one issue at a time. We'll handle the Islamic Republic of Iran and, once that's resolved, we'll make a brief stop on our way back. We'll take care of that," he stated to the media.
With the recent announcement of the agreement with Tehran — despite Iran not officially confirming the final text — that "brief stop" now seems increasingly urgent.
The Escalating Rhetoric on Cuba
Throughout 2026, Trump's rhetoric regarding Cuba has shown a consistent escalation.
On March 5, he remarked to Marco Rubio at the White House, "Your next project will be Cuba."
Further intensifying his stance, on March 27 at the FII Priority Summit in Miami Beach, he declared, "I built this great military. I said I never wanted to use it, but sometimes you have to. And Cuba is next, by the way, but pretend I didn't say that, please."
Amid heightened tensions with Iran, on April 13, Trump once again placed Cuba in the sequence: "Maybe we'll stop in Cuba after finishing this."
The pattern is evident: first Venezuela—with Nicolás Maduro's capture on January 3—then Iran, and finally, Cuba as the third explicitly announced step.
Economic Sanctions and Political Pressure
The pressure on Havana is not merely rhetorical. On January 29, Trump signed Executive Order 14380, labeling the regime an "extraordinary threat" and imposing tariffs on countries supplying it with oil.
By May 1, Executive Order 14404 introduced secondary sanctions against third parties dealing with GAESA, the military conglomerate dominating the Cuban economy.
Foreign companies faced a deadline of June 5 to sever ties with GAESA, and on that same day, Washington sanctioned the Ministry of the Revolutionary Armed Forces, the Committees for the Defense of the Revolution, and the Cuban Institute of Friendship with the Peoples. Since January, the administration has implemented over 240 sanctions against the regime.
The island's situation is dire. Maduro's capture cut between 26,000 and 70,000 barrels of Venezuelan oil daily, accounting for 80-90% of Cuban imports.
The Dire State of Cuba's Economy
Blackouts now exceed 20 hours daily, the generation deficit reaches 2,100 megawatts, and the GDP has plummeted by 23% since 2019, with an additional 7.2% contraction forecasted for this year. According to the UN, infant mortality has doubled to 9.9 per 1,000 births, and essential medicines are at just 30% of normal levels.
On May 28, Axios reported that the administration is preparing for a potential regime collapse "as early as this summer," with the Southern Command conducting simulation exercises for scenarios involving unrest on the island, although officials dismissed the likelihood of an imminent invasion.
Rubio has outlined the conditions with precision: "Their economy needs to change, and it can't change unless their system of government changes. Who's going to invest billions of dollars in a communist country run by incompetent communists?"
Political Stalemate and Diplomatic Signals
Díaz-Canel, meanwhile, has ruled out any political transformation—"my position is not negotiable"—though he confirmed conversations with Washington and released 51 political prisoners in March.
Deputy Foreign Minister Josefina Vidal clarified in April that only "initial contacts" exist, not a structured negotiation. As of March, Cuba had 1,214 political prisoners, evidence that internal repression persists.
Trump encapsulated his strategy on June 4 with a statement that sums up his approach: "We're going to take care of Cuba. And you know what? They are asking for it. The people are asking for it."
Frequently Asked Questions about U.S.-Cuba Relations
What is the current status of U.S. sanctions against Cuba?
As of now, the U.S. has imposed over 240 sanctions against the Cuban regime, targeting entities like GAESA and imposing tariffs on countries supplying oil to Cuba.
How has the capture of Nicolás Maduro affected Cuba?
The capture of Nicolás Maduro has disrupted Cuba's oil imports from Venezuela, which constituted 80-90% of its supply, exacerbating the island's economic crisis.
What are the implications of Trump's strategy towards Cuba?
Trump's strategy suggests an increasing focus on pressuring the Cuban regime economically and politically, with potential for further actions following the resolution of issues with Iran.