Over the past decades, the East German urban condition of post-socialist regeneration, brownfield interim use, and neoliberal policies have created peculiar arenas of place-making. Examining the empirical case of a formerly derelict area within the city of Potsdam, this chapter reconstructs the individual concepts of place identity and the particular imaginaries that heterogeneous stakeholders developed in the first decade of the millennium during a process of communicative local planning. To begin with, ideas prevailed of reconciling separate fields, such as economy and culture, by implementing a trendy municipal planning concept and practicing open stakeholder participation. However, the communication process itself turned out to be increasingly affected by antagonistic top-down and bottom-up perspectives. Representatives of the local state, entrepreneurs, well-established artists, and grassroots “users” of the place not only developed divergent definitions of that place, and imaginaries based on differing social practices, but also found it increasingly difficult to discuss them. The chapter traces this dilemma to differing degrees of individual and group access to structural and interactional power resources.