This case study explores an urban elementary school principal’s efforts to advance reflective and anti-oppressive practices to counter teachers’ beliefs and behaviors toward their Black male students. Data collected and analyzed include five in-depth interviews, focus group discussions, observations of the school, classroom and professional learning meetings, and document analysis of policies, improvement plans, and weekly faculty agenda. The findings revealed that data-informed leadership was the impetus to the principal enacting social justice leadership, which involved anchoring systemic professional learning opportunities to teachers’ core values and beliefs and developing the collective consciousness of teachers individually and collectively. Lastly, the principal utilized strategies and instituted structures in and outside of the school to propel a cultural paradigm shift in how students in general, and Black males in particular, were served and cared for. Implications for principal professional learning and educational leadership preparation programs are shared. This article offers recommendations on how social justice leaders can coach teachers and advance practices that engender respect and dignity for Black male students.