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This paper examines how the United Federation of Teachers built the infrastructure that enabled the NYPD to become a permanent fixture in New York City schools. It explores how the union made intentional, incremental decisions that led to the eventual full-scale involvement of the NYPD in school affairs. Though asked for their involvement to protect teachers and students, police often exacerbated existing problems within schools, yet became the primary arbiters of school discipline beginning in the late 1960s.