While the structural inequities leading to the school-to-prison pipeline (STPP) were well documented in scholarly literature, there was surprisingly little research that centered Black Community Educational Leaders' (BCEL) knowledge and wisdom relative to this injustice. To offer a critical perspective on racial disparities directly targeting Black youth, in a qualitative study this research used storytelling as the methodology to counter the normative (or status quo) way of thinking about Black youth and their lived experiences. Eleven Black Community Educational Leaders who met the established criterion were nominated by members in the local community to participate in a critical case study. The research demonstrated how BCEL possessed profound wisdom to confront and address the root causes of racialized exclusionary practices and structural inequities that affected Black youth in schools and communities. The context of this study focused primarily in the Promise Neighborhood. Historically these were impoverished communities with underperforming schools. For this research, racialized exclusionary practices and structural inequities were viewed through the lens of Black student removal from the classroom that potentially led to a culmination of negative disparate academic and social outcomes. Core findings revealed critical perspectives and wisdom from BCEL about the extensive improvements needed in education and community spaces. Specifically, this research acknowledged historical perspectives and highlighted the importance of high-quality education and equitable opportunities for Black youth.