This research examines Black educators' professional experiences in the School District of Philadelphia (SDP) over forty years, through six superintendents and a state takeover. Using critical race theory, this research uncovers how Black educators' perceptions of SDP, based on district leadership, combined with their interpretations of the historical, social, and political contexts, influenced how they defined their professional situations, interpreted the culture of the District, and how they performed their roles. A phenomenological, historical ethnography approach is employed to investigate person to institution interactions interpreted through the historical record and educators' narratives. This research explores power relations and disjuncture between the goals, assumptions, and rhetoric of the School District of Philadelphia as expressed through its policies, politics, and practices, juxtaposed against the narratives of Black educators. This research found that SDP is peculiar, particular, unforgiving, and deeply politically entrenched. Its politics are complicated by issues of race and insider-outsider tensions and are compounded by state politics and the national political landscape. The politics within SDP were also influenced by the interpretation of the contemporary political narrative by the superintendent and his or her epistemological beliefs and ontological bent within that narrative. / Urban Education