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The virulence of anti-Black racism in the American society has been put on full display with the onset of COVID-19 and the killing of George Floyd. A salient mechanism through which anti-Black racism may be manifested in public education is school discipline. Yet, the influence of school leadership (principals and assistant principals) on suspensions is not fully understood. This study examines the relationship between school leadership and school discipline. Using infraction-level discipline data and information on school leaders’ race from a mid-sized urban district in Southeastern U.S., this study analyzes how Black students’ disciplinary experiences vary by school leaders’ race. The study illustrates several nuances in the relationship between school leadership and school discipline.