The contemporary Cuban regime is difficult to locate in traditional regime categories. It is a personalistic and charismatic dictatorship with an idiosyncratic mix of national-military, egalitarian, anti-American, anti-capitalist, and communist elements. The chapter seeks to ascertain the nature of the contemporary Cuban regime. This is not merely a retrospective or academic exercise. The Cuban regime confronted an economic and political crisis of unprecedented proportions in the early 1990s. The demise of the Soviet Union and its allies deprived the Cuban regime of an important ideological plank. Pluralism in its various dimensions remains underdeveloped and very vulnerable in Cuba, another fact supporting the characterization of the regime as early post-totalitarian. The Cuban regime has always been his in a very special way, but the crisis spawned by the collapse of the Soviet Union and the impending post-Castro era has made him even more indispensable.