Disproportionate disciplinary outcomes for Black male students have persisted across U.S. schools, where these students continue to receive more frequent referrals and higher rates of exclusionary discipline than their White peers. Although district policies provide administrators with considerable discretion, vague and inconsistently applied guidelines often contribute to inequitable disciplinary decisions. While some recent policy shifts have reinforced exclusionary practices, emerging equity-focused leadership approaches offer promising pathways for reducing these disparities. This qualitative narrative case study examined how three principals and three assistant principals in a metropolitan school district in the south employed moral courage, an essential tenet of Transformative Leadership Theory, to reduce exclusionary discipline. Data was collected through semi-structured interviews and reviews of district and school-level discipline documents, then transcribed, coded, and analyzed to identify themes related to courageous leadership behaviors. Five themes emerged: Leadership meaning constructed through storytelling, building equity-centered systems through intentionality, transformative leadership as a values-based identity, developing collective clarity through relational transparency, and navigating ambiguity through adaptive practice. The findings revealed that moral courage was central to leaders’ success in lowering exclusionary discipline rates. Leaders demonstrated the four components of morally courageous leadership by cultivating shared visions of equity, engaging in difficult conversations, communicating with clarity, and navigating ambiguous disciplinary situations with a consistent focus on student wellbeing. Participants emphasized empathy, transparency, and equitable decision-making as critical to building trust, clarifying P.B.I.S. expectations, and maintaining consistency across disciplinary decisions. Their willingness to collaborate with families, support teachers, and seek district guidance further strengthened student-centered disciplinary systems. These results underscore the importance of leadership preparation and ongoing professional development that intentionally cultivate morally courageous leaders capable of disrupting inequitable disciplinary patterns. Ultimately, the study contributes to the growing body of scholarship demonstrating how courageous, equity-driven leadership can foster more inclusive school environments and improved outcomes for Black male students and other historically underserved groups.