The school to prison pipeline (STPP) is a conceptual framework reflecting the injustice that bleeds at the intersection of the educational and criminal justice systems. By drawing on research from a variety of disciplines – including education, psychology, and law – the review of literature examined the contextual factors, including zero tolerance policy and practice, impacting the STPP. The purpose of this phenomenological study was to examine the lived experiences of six men of color and their ability to evade the STPP. More specifically, this dissertation investigated to what capacity the leadership in the home, community, and school contributed to the six men’s ability to evade the grip of the STPP. Constructionism and critical inquiry framed this research that adopted a phenomenological approach. Using their voice and perspectives, the research portrays the men’s lived experience. It is hoped that these narratives can provide educational leaders and the larger society insight into how the six men successfully navigated the K-12 educational system. The key findings pinpoint the structures of support within the context of the home, community, and school that champion justice, success, and equity for boys and young men of color. This study reveals that there is a need for: policy and practice reformation, a closer investigation of restorative justice, demonstration of culturally relevant leadership, and a call for justice.