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This paper will discuss how justifications for police presence in Chicago’s schools shifted from the 1960s to the early 1990s, constituting a gradual mission creep wherein police became ubiquitous in students’ day-to-day schooling experience. Chicago’s educational policymakers called for and justified the presence of police in schools for a multitude of reasons, calling for officers to act as mediators of desegregation, warriors in the battle against gangs and drugs, and role models for students to emulate and even befriend. Interestingly, as national and local perceptions of youth shifted, so too did the rhetorical justification for police to patrol the halls of Chicago’s schools. Using archival sources, newspaper accounts, and education and police publications, this paper will trace how administrators and education stakeholders justified the presence of police, and how those justifications changed over time. Ultimately, this study reveals how structural racism, false notions of cultural pathology, and school segregation worked to legitimize police presence in schools, merging education and law enforcement in ways that have proven surprisingly durable.