As the Cuban regime faces growing protests and intensifying blackouts, President Donald Trump reiterates almost daily that he expects to have the “honor” of “taking Cuba in some form.” With an oil quarantine already in place, Raul Castro’s cadres are already feeling the heat.
In a rare press conference on March 13, Cuban President Miguel Diaz-Canel finally admitted that the regime was in talks with the United States after three months without fuel imports to the island. Seated close by was Castro’s grandson, who met with Secretary of State Marco Rubio on Feb. 25.
Since Diaz-Canel’s press conference, emboldened protestors have taken to the streets and set fire to a communist party office in Moron, and the island plunged into darkness on March 16 after the entire power grid went offline.
Despite these events, more pressure may be necessary for the Trump administration to secure a deal that will bring about political change in Cuba. After all, the regime created by late dictator Fidel Castro has survived many shocks over seven decades: the Cuban Missile Crisis, the fall of the Soviet Union, and, more recently, massive protests in 2021, which were followed by nearly one-fifth of the population leaving the country.
CUBA’S CRISIS IS CLOSER, AND MORE DANGEROUS, THAN WASHINGTON THINKS
Here’s how the Trump administration can squeeze the Cuban regime even further to create leverage for a successful deal.
First, keep the threat of military operations on the table. The fear of potential military action maximizes U.S. negotiating leverage and will keep Diaz-Canel and the regime’s military and intelligence apparatus looking over their shoulders. This does not mean that military operations should be the administration’s first choice or are even likely to happen. But in the aftermath of the capture of Venezuelan dictator Nicolas Maduro, a key Cuban ally, the threat of military action is far more credible and therefore useful in achieving a potential deal.
Second, launch a comprehensive campaign to choke off cash flows to the regime. Recent reporting indicates that GAESA, the Cuban military’s business conglomerate that controls large portions of the economy, holds as much as $18 billion in reserves from tourism and other ventures, while the Cuban people can barely access power and water. The Treasury and the Department of Justice should stand up a task force to go after Cuban shell companies in both the U.S. and Europe that support the regime by circumventing U.S. law and freeze regime assets overseas.
Trump should also authorize secondary sanctions on foreign entities that engage in financial transactions with entities on the State Department’s Cuba Restricted List. This list includes GAESA and other businesses and institutions tied to the Cuban security apparatus. Secondary sanctions would send a clear message that the United States will no longer allow Canadian and European tourist dollars to line the pockets of a military and an intelligence service that work with China, Russia, and Iran to spy on some of America’s most important military installations. For the regime, this move would signal that waiting out the U.S. will not succeed because foreign cash is not coming back.
Finally, the U.S. should strengthen its support for the Cuban people. American food assistance through the Catholic Church should continue, and the U.S. should encourage other partners to use the same channel so the regime cannot divert aid. To break through regime censorship and provide critical information to the Cuban people, the administration should surge resources to Radio y Television Marti and other Office of Cuba Broadcasting programs to ensure continued access even amid power and internet blackouts.
CONGRESS MUST CALL TIME ON THE INTELLIGENCE COMMUNITY’S HAVANA SYNDROME COVER-UP
Congress also recently provided additional funding for democracy programs in Cuba that the administration can leverage to support Cuban dissidents and civil society as they push back against regime repression.
Trump has a historic opportunity to help the Cuban people take back their country after 67 years of communist rule and end a significant national security threat 90 miles from Florida. While change in Cuba has never come easily, this time could be different with the right pressure from Washington.
Connor Pfeiffer is senior director of government relations at FDD Action and a former congressional staffer who worked on Western Hemisphere policy in the U.S. Senate and House of Representatives. He can be found on X @ConnorPfeiffer.
