Schools are not neutral. They fuel cultural reproduction – actively ensuring predictable outcomes for students with similar demographics – through everyday practices and embedded systems or ways of operating. Educational leaders are imperative to challenging and changing problematic practices in U.S. schools, since they play a significant ongoing role in the adoption, implementation, sustainability, and effectiveness of school-based design and interventions that close educational outcome gaps. Black school leaders are an invaluable source of information regarding the subversive actions needed and enacted to meet the needs and brilliance of students and families, and thus also to explore what is needed to close existing educational outcome gaps. This dissertation explores how Black school principals’ life experiences shape their subversive leadership framework – the set of core beliefs and practices that exemplify their commitment to disrupting the cultural reproduction perpetuated through U.S. schooling system. It also distills the support necessary at the district level to support this disruption. According to these leaders, a subversive leadership framework requires acts of conspiring that create the conditions for equitable experiences and outcomes for students, including strategic actions to circumvent systems and practices that disadvantage marginalized students and communities; actions that protect and prepare children for their own subversive actions; and commitment to the health of the school ecosystem, including adults within the school as well as families. The methodology includes semi-structured interviews, and diffractive analysis is employed in both data collection and analysis.