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By the end of the Cold War, US-Cuba relations have been characterized by the American efforts to promote democracy in Cuba: democracy promotion has become the cornerstone of the American policy toward the island and its socialist government. After George W. Bush's two terms and the consistent backlash against US democracy promotion worldwide, Obama's strategy has been depicted as a partial retreat from the posture of his predecessor. In the midst of Raúl's reforms in Cuba, it is necessary to explore which has been the evolution of the concept and praxis of US democracy promotion under Obama. Is the “Obama doctrine” in democracy promotion applicable to US-Cuba relations? How will Obama's new course in democracy promotion affect the future relations with Raúl's government? These are the central questions this paper wants to explore.