African American males are three times more likely than their White male counterparts to be suspended or expelled in public schools. Changing these odds requires not only addressing disparities in discipline practices, but also lifting up a new narrative of hope, possibility, and brilliance so that young Black men can see and realize their potential. In 2010, Oakland Unified School District (OUSD) Superintendent Tony Smith, Oakland's Board of Education, the Urban Strategies Council, and the East Bay Community Foundation concluded that past efforts to improve the educational experiences and supports of African American male students in OUSD had changed little for this student population. They determined that real change would require a culture-shifting commitment by the school system. To institutionalize this commitment, OUSD launched the Office of African American Male Achievement (OAAMA), a bold project created to fundamentally improve academic and life outcomes for African American male students in Oakland, making OUSD the first district in the United States to create a department specifically to address the needs of African American male students. OAAMA Director, Chris Chatmon, and his colleagues have courageously and creatively cultivated new forms of interactions, relationships, rituals, and practices between young Black men, educators, parents, unions, district staff, community members, and organizations. Richard Gray, Director of Community Organizing & Engagement at the Annenberg Institute for School Reform at Brown University, sat down with Chris Chatmon to discuss the path and steps he has taken to create and sustain his program. This article focuses on how Chris's program reaches, uplifts, and educates Black males. OAAMA's approach to changing the outcomes for young Black men in OUSD is centered on the belief that every interaction, no matter how small, impacts the culture and the lives of young people. In fact, it is these many small interactions that often matter the most.