Donald Trump is a teetotaler, but his fondness for the original Cuba Libre is impossible to ignore. On Wednesday, he commemorated Cuba’s Independence Day with a statement reinforcing CIA director John Ratcliffe’s earlier message to Havana that time is running out to address his concerns. The same day, the Nimitz aircraft carrier group arrived in the southern Caribbean, and the Department of Justice announced an indictment of Raúl Castro and several underlings for shooting down American civilian aircraft in 1996.
As Secretary of State Marco Rubio told the Cuban people in Spanish, the U.S. government wants a new and better relationship with Cuba and has offered to distribute aid money through the Catholic Church or other non-regime channels to alleviate their suffering. A Castro-free Cuba, or one that significantly improves its treatment of its own people and respects American interests, would be a major accomplishment for Trump.
Cuban freedom has long been a cause for Americans. Sometimes they have hoped for the island to join their republic, but they have given the independence movement substantial support too. The Cuban flag was designed and first unfurled in New York City in 1850, and Cuban patriot extraordinaire José Martí organized from there the movement that eventually ended Spanish imperial rule. Cuban Americans may have a special antipathy for the Castros, but many other types of Americans also extend the blessings of liberty southward.
Americans tend to move from passive sympathy to action when threats to their own interests arise from Cuba. President McKinley sent in troops in 1898 because Spain’s attempts to suppress the independence movement there threatened to spill over onto American shores. John F. Kennedy ham-handedly tried to oust the Castros and nearly went to war when the Soviets stationed nuclear weapons on the island.
The threat posed by the Castros faded after the Cold War, but recent developments have made it more ominous. A January executive order noted, “Cuba hosts Russia’s largest overseas signals intelligence facility,” “continues to build deep intelligence and defense cooperation” with China, and “welcomes transnational terrorist groups, such as Hezbollah and Hamas.” Havana has also reportedly received hundreds of attack drones from Iran and Russia, some of which may have the range to reach Florida.
Unfortunately for the Cuban people, their masters in Havana have been more eager to provoke Washington than to improve their lot in life. The Castros lamely blame their economic failures on the U.S. trade embargo rather than on the predictable result of central planning, but they have no interest in an open economic relationship with any country—especially the United States. Havana routes the best economic opportunities into the military-run GAESA organization and plowed nearly half of the country’s investments since 2019 into catering to international tourists. Socialism for the rich indeed.
This arrangement worked while Venezuelan oil subsidized Cuban failures, but it ended in January when the U.S. military seized Nicolás Maduro, who was also under indictment and now awaits trial in Brooklyn. The Cuban Communists are discovering their planned economy does not have anything near the vibrancy and resilience to survive. The island has only received one oil tanker since December due to U.S. pressure, and the energy minister admitted last week that his country had run out of oil and diesel. Many places receive electricity a couple of hours a day at most. The economic situation is dire, and protests are breaking out in Havana.
Capitalizing on Cuba’s weakness could result in major achievements for Trump. Ushering out the Communists would thrill significant portions of his base, particularly the right-leaning Latin American voters who despise socialism. It would also devastate the global left, which prizes irritating or threatening Americans more than improving the lives of the global poor and thus has adored Cuba since Fidel Castro seized power nearly 70 years ago. This operation would come with transatlantic backing too: Poland is offering to share with a post-Castro Cuba its experiences transitioning away from communism.
Achieving that goal might require a second attempt at a Maduro-style operation, which would be risky. Havana admitted that 32 of its commandos died trying to protect their Venezuelan patron, but its military has presumably learned from that defeat. And if no successor is ready to seize control and make a deal with Trump, internal fighting so close to American territory could rebound in unpredictable ways.
An agreement that leaves the regime in place but opens more opportunities for Cubans and kicks out our adversaries would still greatly enhance U.S. national security. It might not be as satisfying at home, but it could still be the greatest development in the Cuban-American relationship in decades.
Aeroflot still flies from Havana straight to Moscow. Raúl should book soon. The price will get steeper every day.
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