Those tasked with leading large school districts direct incredibly complex organizations in what are often contentious political and social contexts, with powerful stakeholder groups espousing conflicting policy priorities. Because of their high-profile positions, superintendents often face uniquely persistent and powerful resistance and must navigate this complex decision- and policy-making atmosphere in order to effectively promote durable, long-term equitable change. This case provides useful lessons on advocating for equity from the superintendency and provides space for reflection on the practical implications of leading for equity in a dynamic and potentially fraught leadership environment.