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Black students in low-income U.S. communities face deep-rooted structural inequities—including poverty, homelessness, food insecurity, violence, and systemic anti-Blackness—that severely impact their academic success. This study uses portraiture methodology to examine how school leadership at one community school in Los Angeles supports Black students through a holistic, equity-centered model. By integrating academic support with mental health services, Black family engagement, and community partnerships, the school addresses students’ basic needs while fostering safety, stability, and trust. The research highlights how leadership practices within community schools can disrupt systemic barriers and improve outcomes such as attendance, graduation rates, and access to advanced coursework. Ultimately, the study shows how community schools can promote student agency, liberation, and reimagined possibilities for Black educational and personal success.