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This paper explores selected policies of Mayor David Dinkins’ administration involving youth, education, and public safety. It provides an overview of perceptions of violence and Black and Latinx youth in 1980s NYC and chronicles the remarkable way its first Black mayor saw investments in schools, youth, and community programs as viable options for crime reduction, economic growth, and urban revitalization. Scholarship on schools and urban youth during this era often focuses on punishment and surveillance, missing how policymakers used educational programs as spaces to affirm, encourage, and inspire young people. This paper uplifts the work of a historic administration as it reimagined what youth-centered programming and radical care for young people in a city could do for its future.