Thirty-two Cubans died when American forces entered Caracas on January 3, 2026, to capture Nicolás Maduro. Cuba and Venezuela are more than a thousand miles apart. Why were Cubans dying in defense of Maduro? How did a small Caribbean island become so deeply invested in the survival of another country’s dictatorship?
To answer those questions, we have to go back nearly seven decades to a revolution that promised liberation but spent a lifetime exporting authoritarianism and reshaping the politics of an entire hemisphere.
From the moment he seized power in 1959, Fidel Castro knew that the survival of his revolution depended on its spreading throughout South America. In the years that followed, Havana trained Marxist guerrillas across Latin America, dispatched troops to fight Soviet proxy wars in Africa, supported Syria in its war against Israel, and embedded intelligence officers inside allied dictatorships. Today, it’s widely reported that Cuban nationals are fighting alongside Russian forces in Ukraine.
If there is one lesson the Cuban regime has taught us, it is that dictatorships do not always have to become stronger to survive. Sometimes they survive by becoming indispensable to stronger powers. For Cuba, the Soviet Union came first. Then Chávez’s Venezuela. Today, Russia, China, and Iran have each found value in keeping the regime afloat. Cuba has vexed every American president since Eisenhower not because it is economically or militarily powerful, but because it has repeatedly positioned itself as the hemisphere’s most persistent hub of anti-American influence.
Join the conversation as a VIP Member