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The case study seeks to explore the differences between traditional and charter school leadership preparation. Using the theoretical framework of interest convergence, we explore the ways in which mostly-white led large CMOs are being challenged to consider alternative ways, further understanding, and application of more traditional leadership preparation practices. We explore the ways that a charter system’s internal development practices may reproduce leadership that fails to value the experiences and expertise of leaders of color. We raise questions and illuminate potential gaps within practice that could have impacts on student and community outcomes, in hopes of calling others in education research to explore both traditional and charter school practices.