This qualitative study explores the potential in creating Freirean culture circles in an independent school (Star School), while interrogating issues of belonging, power, and systematic racism faced by African American families (and specifically their middle school-aged sons). An essential element in this project is the self-study of the author as he elevates the core question of whether it's possible for a reflective leader to galvanize the historically dominant population of White, multigenerational independent school faculty, board, and enrolled families toward an improved, dialectic ethos with African American families. The conceptual framework in this research intertwines critical race theory, black feminist theory (and resistance), and Paolo Freire's process of creating belonging through culture circles. Within the self-study element of this project, there are also reflections on leadership practice, case study analysis, and authentic suggestions toward an improved African American Parent-Star School partnership.