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This paper is based on extensive fieldwork examining how homeless and other very poor people were policed and otherwise regulated in the spaces outside of a transportation center in Jersey City, New Jersey, as well as several months of research on homeless “hot spots” and encampments in New York City. In the various spaces that I studied during the course of these research projects, I observed a set of conditions that defy what has historically served as the primary justification for Broken Windows policing and other aggressive order-maintenance policing strategies. That is: “disorder” and petty criminal behavior, if “left unchecked,” will engender ever-greater levels of disorder and eventually serious crime. This prediction has not held true in my research. To the contrary, I routinely observed homeless people and others engaging in behaviors that proponents of aggressive order-maintenance policing have regarded as quintessential examples of criminogenic disorder. By and large, these behaviors were left unchecked by the police. And yet, in these very same “disorderly spaces,” rates of serious crime were quite low—in some cases, historically low. My paper examines the theoretical and practical policy implications of this finding.