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This qualitative study examines an out-of-school learning environment focused on gun violence prevention among gang-affiliated youth on Chicago’s South Side. Specifically, I examine the role of trust within the learner-educator relationship and how participants’ educational aspirations change over time within the out-of-school learning environment. Through longitudinal analysis of three rounds of interviews and 45+ hours of observational data, findings present a taxonomy of the ways the program cultivated trusting learner-educator relationships such that learners felt safe, cared for, and free to dream of and enact joyful futures, despite structural racism. The paper offers theoretical and practical contributions for culturally responsive and effective learning environments specific to gang-affiliated youth, providing practitioners and policymakers an evidence-base toward transformative education reforms.