Downtown São Paulo is the stage for public disputes over memory, narrative, and the future. This study examines the region’s various cycles of settlement, depopulation, and resettlement as long-term effects of conflicting ideological paradigms and models of urban sociability, produced and channeled by communication across different eras. Based on a theoretical review, this study links the European matrix of modernity—associated with the valorization of urban life and public life—to the shift promoted by the American paradigm of the “American Way of Life,” characterized by the automobile, the consumption of household appliances, and the desirability of the suburbs. Finally, under neoliberal rationality, it is argued that the privatization of sociability, the centrality of consumption, and the culture of fear intensify the rejection of the commons, legitimizing selective and walled-off spaces. The study further concludes that the city center has been progressively abandoned by the elites as an endorsement of distinct symbolic paradigms of urban life and that, in the same vein, contemporary repopulation agendas tend to appeal to and invite the very same dominant segment that historically distanced itself from the area.