What do we do with the monuments from the socialist past? This question continues to resurface with relentless persistence in Bulgaria’s public life. For the past twenty-five years, socialism’s monuments have suffered severe neglect, yet they have provided open terrains upon which different political forces have taken on grassroots forms to articulate their perspectives against each other and vis-à-vis the country’s socialist history. Thus, while discarded as remnants of a failed political experiment, they have become those peculiar sites without which postsocialist political and everyday life is hard to imagine. This essay focuses on two particularly contested monuments from two distinct periods of Bulgaria’s socialist era, Plovdiv’s Monument to the Soviet Army, or “Aliosha,” from 1957, and Sofia’s Monument to 1300 Years of Bulgaria, from 1981. It offers a historical reconstruction of their creation and a critical interpretation of their political and cultural meanings under socialism, while also chronicling their reconfigured everyday and political uses during the postsocialist years. Studying their intricate governing functions in public space, the essay argues that these open and dynamic microworlds continue to organize community life and leisure in particular ways, while defying the privatization of public space and the normative imperatives of neoliberal urban development in the postsocialist city.