This article examines the 2019 Hong Kong protests from the perspective of urban space and the city's historical founding as a colonial entrepôt. Specifically, it explores how the protests destabilized both the urban fabric of the city and the political and economic agreements that have defined the city's governance since handover. The analysis of the protests, and of the history leading up to them, is informed by writings on democracy and space by Chantal Mouffe and Doreen Massey, and considers the work of activists, researchers, and journalists whose voices have often been out of step with the movement and with international media narratives that have defined it. The article provides historical and theoretical insight into the role of both collaboration and conflict in the formation of the city's political identity and points to possibilities for engaging with the still‐open question of the meanings and practices of democracy in Hong Kong.