For two years in the late 2000s, a 14-block-long stretch of pavement became the site of conflict in Brooklyn, New York. The City of New York abruptly installed then uninstalled what became a contentious bike lane, creating a shock and fomenting a new cultural fissure in a rapidly gentrifying neighborhood. This chapter explores how institutions react to change and the territorial and temporal consequences. Specifically, it examines the City’s role as an institutional mechanism that both implements and reacts to the functionality of public space. This is a qualitative microanalysis of the political, economic, and social conditions that led to the Bedford Avenue bike lane becoming a space of conflict. History matters here. For decades, the Williamsburg neighborhood was tensely shared territory for Latinxs and Hasidic Jews, who both settled there in the mid-twentieth century. Later, Williamsburg became the forefront of New York’s rapid economic change and gentrification. While the urban planning logic of installing the bike lane may have been sound, the City did not adequately consider its symbolism as a manifestation of permanent spatial and territorial change. After two years of community conflict, the City reversed course and removed it, literally erasing the bike lane’s existence. The consequences still play out every day in local cultural and political dynamics. The analysis examines how policymaking can be engineered to mitigate potential negative outcomes to change in shared public space in urban neighborhoods. This research is particularly relevant now; street redesign is having an in-vogue moment with urban policymakers, planners, and designers. The findings speak to how municipal policymaking bodies can more productively harness local knowledge and power to make effective and equitable change, while mitigating negative backlash and disassembling outdated institutions that obstruct positive transformation.