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Black male educators remain underrepresented in U.S. K-12 schools, and their experiences as students and teachers are shaped by intersecting social, institutional, and historical conditions. This qualitative study examines how Black men make meaning of their experiences within educational systems throughout their lives, including schooling, teaching, and post-classroom engagement, providing context for ongoing discussions of Black male educator attrition. Guided by African American Male Theory (AAMT) and Interpretative Phenomenological Analysis (IPA), this study uses semi-structured interviews with five former Black male K–12 educators connected to an Afrocentric, community-based cultural platform. Analysis identified six interconnected themes: personal growth and healing; disruptors of adverse patterns; vulnerability, fetishization, and care; polarizing experiences and stereotypes; community and healing; and the implications of historical misunderstanding. These themes were examined across ecological levels to situate participants’ meaning-making within individual, institutional, community, and sociohistorical contexts. Findings illustrate how Black men make meaning of their experiences as students and educators and how this meaning-making shapes their engagement with education before and after K-12 service.