This paper examines how the transformation in UNESCO’s policy towards urban conservation—from a narrow emphasis on architectural conservation to a broader focus on urban heritage management—plays out in the context of Old Havana, a UNESCO World Heritage site. In particular, we argue that this policy shift in the Cuban case gives rise to a new form of governance that encourages the creation of a new type of ‘socialist man’ (hombre novísimo) through the disciplining of and shaping the participation in cultural production of heritage. This new form of governance is particularly pronounced in the Cuban context given the centralization of power in a single, entrepreneurial sub-state actor, the Office of the City Historian of Havana (OHCH) that manages the territory and its population on behalf of the Cuban state. Moreover, given the fact that the state controls all of the patrimony in Cuba further accounts for the OHCH’s ability to govern and dispose of territory and population in ways that are complicated in liberal polities that must negotiate with the demands of private developers and property owners and institutionalized forms of public accountability. The Cuban case is particularly interesting then given the fact that historic centers like Old Havana play an increasingly important role in Cuba’s tourism-oriented development strategy together with the survival of quasi-socialist institutions in the post-Soviet period (cf. Colantio and Potter 2006). Francesco Bandarin and Ron van Oers’ recent book (2012), on the historic urban landscape testifies to the importance of the Old Havana case through a case study that depicts the Old Havana experiment in combining urban landscape conservation with a dynamic form of urban development that is officially known as ‘comprehensive development’ (desarrollo integral).