This chapter explores the contrast between Taiwan’s Sunflower Movement and Hong Kong’s Umbrella Movement as a natural experiment in comparative policing. I look at the different roles played by police within the larger historical dynamics of these two events. My goal is to distinguish the democratic qualities of Taiwanese policing from the more authoritarian qualities evident in Hong Kong. I develop a theoretical framework for analyzing this distinction by combining Peter Manning’s idea of police dramaturgy with Victor Turner’s theory of social dramas and Carl von Clausewitz’ approach to violent politics. This perspective, I argue, helps illuminate how the democratic qualities of police action in response to unsettling events can influence the longer historical/structural patterns linking what comes after to what went before.