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Hip Hop is an underexplored ideology and practice of p-20 school leaders. This paper, a collective testimonio assembled by the co-authors who also act as participants, presents a conceptualization of Culturally Sustaining Hip Hop School Leadership (CSHHSL). Constructed from analyses of the co-authors experiences as p-20 school leaders, the five elements that make up CSHHSL--sampling, coding, blending, knowledge of self, and creating and maintaining the cypher--are intended to support other p-20 school leaders in creating and sustaining more loving, equitable, and just educational conditions for their staff, students, their families, and the communities that they serve.