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Cuba is probably one of the best examples of the significance of the democracy promotion discourse in US foreign policy: the efforts to democratise the island have been one of the main features in the US—Cuba bilateral relations since the end of the Cold War. Even the embargo against the island has evolved from a tool to generate regime change to an instrument of democracy promotion to foster a democratic transition. Today, the Cuban embargo, after the codifications of the 1990s, is intimately connected to a ‘Cuban democratic future’. Moreover, in the last three decades, US presidents have committed themselves to promote democracy on the island, inaugurating a sort of ‘state policy’ with little or no evolutions or changes. The main aim of this two-part article is to explore the rationale behind US decennial efforts to promote a peaceful democratic change on the island, while trying to answer some crucial questions about US strategy in Cuba: Why promote democracy in Cuba? Why did democracy promotion become a long-lasting feature in US—Cuba relations? The first part deals with the security framework, and American economic interests in Cuba as a crucial push factor for democracy promotion, while the role of the Cuban-American community and the problems and perspectives of US strategy will be included in the second part, to be published in the next issue of the Journal.