Educational leadership plays a vital role in improving the academic outcomes of underserved and minority students. The leadership practices of Black educational leaders have contributed to the theorizing of effective, culturally responsive practices to improve student outcomes. This article uses portraiture to look at how one former Black principal leans on his indigenous understanding of his school and community to build a generational legacy of Black educators and educational leaders. Indigenous, in this context, is used to describe this principal's connection to the community from birth to his retirement and beyond. The article ultimately asks, what contribution does being Indigenous to a space and place add to our understanding of educational leadership and the educational leadership of Black administrators?