Beginning with the renowned “Words to Intellectuals” (1961) delivered by Fidel Castro in the José Martí National Library and the creation of a state network of libraries, the library in Cuba was transformed into a cultural sphere saturated with ideological ambiguity. On the one hand, the library embodied the symbolic axis of the literacy campaigns and of reading as the catalyzing nucleus of revolutionary volunteerism and of the imagined solidarity among Cubans of different social classes. But the library also constituted the foundational scene of the enduring uncertain relationship between the state and intellectuals embodied in Fidel’s directive “within the Revolution, everything; against the Revolution, nothing.” In this context, the representation of the library in post-Soviet Cuban literature and film re-stages unfinished debates between freedom of expression and the social contract. Drawing on concepts from Foucault, de Certeau, and Benjamin, this analysis demonstrates that recent Cuban cultural production re-invigorates the library as a space of ideological negotiation in a period of precarious expectations and re-activates cultural conversations about social class and democratization; individual and collective ownership of cultural resources; and the revolutionary ideal of citizen immersion in cultural life.