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Although administrators and teachers are often perceived as a team, we found the fractures in these team structures to be a major catalyst for urban teachers’ departures from the profession. This paper shows the importance of educational administrators in the career development of teachers through the life histories of former urban teachers. Teachers reported that administrators adopted an “us vs. them” mentality as well as “inner circle” politics. But we also share the storied experiences of strong and supportive administrators and the lessons from their leadership. We provide implications emerging from both strained and positive teacher-administrator relationships, and how these lessons can be applied to future administrators and teacher educators.