The article is devoted to the history of terrorist organizations that arose as a response to the Cuban Revolution of 1959, the rise to power of Fidel Castro and the policies of his government over the following decades. An important role in the creation, financing and support of these organizations was played by people directly or indirectly connected with the American special services and the political leadership of the United States. The activities of Cuban counter-revolutionary terrorists have led to tragic consequences, including the deaths of innocent people, not only Cubans, but also representatives of other Latin American countries. The use of terrorist methods for political purposes is an extremely urgent problem in the 21st century, and therefore an appeal to the history of this phenomenon is objectively necessary to effectively combat this evil. The history of terrorist activity by opponents of the Castro regime is of interest both to historians and political scientists, whose interests include the study of the Caribbean region, the history of foreign policy and the activities of US intelligence agencies, and to specialists in international relations in general. The methodology of the research is based on the principles of historicism, scientific objectivity and consistency. This allows us to consider the problem under study as an integrated system, where the facts are analyzed in their entirety and interrelationships. General scientific (analysis and synthesis, induction and deduction, descriptive) and general historical (historical-comparative, historical-systemic) research methods are necessary for conducting research. The present study has a scientific novelty, since it is based on sources not previously used in the Russian scientific literature. A significant part of the corpus of sources used by the author of the article are classified CIA documents until recently. To a certain extent, working with such arrays of information is not only a historical, but also a political science study that allows us to better understand the realities of modern geopolitics. As for the conclusions of this study, they may be summarised respectively: 1) the United States, at least in the recent past, was a direct sponsor of international terrorism; 2) the activities of anti-Castro terrorist groups in the 20th century still hinder the process of restoring diplomatic relations between the United States and Cuba; 3) a violent change of power in the state inevitably generates a cycle of violence that evades the risk of interference in the internal affairs of the country from the outside.