This article examines change and continuity in the United States' recent foreign policy toward Cuba. In the context of the posthegemonic regionalism of the Pink Tide and regional disputes over Cuba's position in the interamerican system, the Obama administration's rapprochement was driven to protect the institutional power and consensual features of U.S. hegemony in the Americas. The Trump administration reversed aspects of Obama's normalization policy, adopting a more coercive approach to Cuba and to Latin America more broadly. Against the emerging scholarly proposition that the international relations of the Americas have crossed a posthegemonic threshold, this analysis utilizes a neo-Gramscian approach to argue that the oscillations in U.S. Cuba policy represent strategic shifts in a broader process of hegemonic reconstitution. The article thus situates U.S. policy toward Cuba in regional structures, institutions, and dynamics.