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African American principals are more likely to lead schools serving large numbers of minority students, high concentrations of students affected by generational poverty, and schools plagued by consistently low academic performance. Many schools of this type exist in urban settings and often need intensive support. Schools reflecting these characteristics are often labeled negatively due to punitive accountability standards. They also tend to experience high levels of leadership volatility. Using qualitative interview data gathered from African American, male, urban school leaders, findings indicate that the lack of quality mentoring and support contributed to limited professional growth and development and potentially career derailment. It is strongly suggested that effective and prescriptive wraparound support structures for these leaders are urgently needed.