This paper analyzes the relationship between media and politics in Cuba during the presidency of Raúl Castro (2006–2018). It contributes to the theoretical discussion about the approaches concerning change and continuity in media systems with empirical evidence from interviews with communication and political science experts, and an analysis of non-standardized content in academic, political, legal, and professional documents. The (re)structuring of the media system is explained by the most important political, economic, technological, and cultural events of the period studied: the survival of the Soviet media model, the impact of the U.S. conflict with Cuba on domestic politics, and a (de)territorialized notion of system boundaries. The patterns of change and continuity are discussed through the relationships among the State’s participation in media and the fulfillment of media’s democratic functions, the media policy projection and journalism cultures, and the political articulation of the media and development of the media industry. The articulations among these patterns highlight the relevance of a multidimensional approach as an interpretive dimension of media systems.