Black boys in racially segregated urban schools are vulnerable to the trappings of the school-to-prison-pipeline. In this article, I use narrative inquiry and critical race theory (CRT) to examine the stories of two elementary school principals struggling to create more inclusive schools for Black boys with emotional disabilities (ED) in a racially segregated and low-performing district. Each principal narrative describes efforts to transition a student with ED from a district-created self-contained program to a full-time or near-full-time placement in an inclusive general education classroom. Despite the principals' overall success in creating more inclusive schools for most students with disabilities in a challenging district context, each principal narrative ends with a student being unsuccessful in an inclusive setting and returned to a segregated program. The findings highlight how principals who recognize the vulnerability of Black boys in special education are compelled to create more inclusive schools, but can confront significant institutional, organizational, and social and emotional challenges. Applying CRT to these cases provides additional insights into how principals can develop inclusive schools and challenge segregated programs. While some inclusive leadership practices aimed at improving the educational outcomes of Black boys are identified throughout these narratives, the significance of the study lies in documenting and understanding how principals experience the barriers and challenges to creating more socially just and inclusive schools.