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This study examines the experiences of Black administrators in California Community Colleges as they navigate anti-Black institutional cultures while advocating for Black student success. Using qualitative critical narrative inquiry and guided by BlackCrit and Black Feminist Theory, it explores how systemic anti-Blackness shapes their leadership and transformative efforts for Black students. The findings reveal the dual realities of joy and pain in leading institutions and supporting Black students. By centering their voices, this study highlights strategies for confronting anti-Blackness and reimagining leadership practices to improve conditions for Black students. It offers actionable insights for dismantling anti-Blackness while fostering environments that humanize and empower Black students and Black leaders.