Trump may be headed toward a pointless confrontation with Cuba
The president seems to think he may be the one to finally squelch the Communist regime. Does he realize how few good options he has?
By Stephen Kinzer – Boston Globe - February 4, 2026
Is Cuba next? That question has been on many minds since American commandos seized President Nicolás Maduro of Venezuela last month and flew him to a prison in New York. By doing so, they decapitated a defiant leftist regime in the Caribbean Basin. Some are tempted to hope that Communist rule in Cuba can also be brought crashing down.
That is highly unlikely. National uprisings require a broad-based, organized political opposition, preferably with a charismatic leader. Decades of repression have made it impossible for any of that to emerge in Cuba. The regime has deep roots, is highly organized, and counts on many passionate supporters. Kidnapping a single leader, or even all senior leaders, would not bring it down.
The only way the United States can impose its will on Cuba would be through invasion and occupation. President Trump seems in no mood to consider that. Instead, he has suggested that he will impose more drastic sanctions that would cut Cuba off from the outside world. “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA - ZERO!,” he posted on social media last month. “I strongly suggest they make a deal, BEFORE IT IS TOO LATE.”
Cuba relies on imported oil to keep buses running and to support its electrical grid, which is vital to the functioning of water pumps, hospitals, and schools. Cutting off the supply would be devastating. If Trump wants to go even further, he has plenty of other tools. He could end flights to the island, stop allowing American medicine to be shipped there, or ban the cash remittances that Cuban Americans send to support their families. He is reportedly considering a naval blockade, which could prevent even the importation of food.
These steps might be illegal under international law, but that concept is out of favor in the White House. The administration has justified its campaign against Cuba by saying that its government supports “numerous hostile countries, transnational terrorist groups, and malign actors adverse to the United States” and that it “blatantly hosts dangerous adversaries of the United States.”
Punishing Cuba for defying American power is nothing new. Cuba has been under US sanctions for more than 60 years. President Kennedy imposed a near-total trade embargo in 1962 — the day after he sent his press secretary to search Washington’s cigar stores and buy him 1,000 Cohibas for his personal use. Today the United States remains the only country in the world where it is illegal to buy or sell a Cuban cigar.
President Obama relaxed the sanctions and even visited Havana in 2016. If his successors had taken the same approach, Cuba would be a very different place today. Neither Presidents Trump nor Biden, however, showed any interest in returning to Obama’s policy of engagement with Cuba.
Conditions on the island have worsened drastically in recent years. The government has devised a simple solution to popular discontent. Instead of arresting those who protest or are unhappy, it allows them to emigrate. In the last five years, an astonishing 1 million Cubans have left their homeland, nearly 10 percent of the population. About half of those who left have made their way to the United States.
Tightening the screws on Cuba could send Cubans toward starvation. At the very least, it would make them more miserable and probably lead more of them to emigrate to the United States. It would not, however, produce regime change.
The United States has the power to create a humanitarian crisis in Cuba. Pictures of emaciated Cuban children could then flash around the United States and the world. That would be a propaganda loss without any political benefit.
Finding someone in the upper reaches of the Cuban government who would betray it is also a fantasy. American intelligence knows little about the Cuban power structure. Even if it could identify a possible collaborator, it would have no way to reach that person without setting off alarms in Cuba’s efficient counterintelligence service.
If the United States could somehow make the entire Cuban leadership disappear, the result would probably not be a pro-American government. The military, which is strong and better respected by Cubans than the police, would be likely to step into the vacuum. A possible leader would be General Alejandro Castro Espín, a nephew of the late Fidel Castro.
Among the farthest-reaching consequences of American military intervention in Cuba might be a Chinese strike against Taiwan. What better justification could there be than “We’re only doing in Taiwan what the Americans are doing in Cuba”?
Every American president since Thomas Jefferson has sought to bring Cuba under Washington’s influence. Cuban outrage at repeated interventions finally produced the 1959 revolution that brought Fidel Castro and his militantly anti-American regime to power. Now the anti-Cuba drive is reaching new intensity, in part because Secretary of State Marco Rubio is of Cuban descent and shares his community’s obsession with deposing the Communist regime.
Like his predecessors, Trump has a hard time treating Cuba as a sovereign state. Unlike them, however, he may be interested in the enormous potential for tourism and real estate development there. Cuba seems ready for a live-and-let-live deal with the United States. Whether Trump is ready remains uncertain. If his approach changes from confrontational demands to honest negotiation, a breakthrough is entirely possible.
Stephen Kinzer is a senior fellow at the Watson School of International and Public Affairs at Brown University.