Black male teachers possess an epistemological and pedagogical stance that is largely different from their non-color counterparts. Having a nontraditional stance can be problematic when evaluated by school leaders who hold traditional views of teaching and learning. Where many Black male preservice teachers enter the profession with desires to be a difference maker to marginalized communities, they often find pressure to acquiesce to Eurocentric educational norms or face isolation. As such, we find increased retention issues to an already limited teacher population. This study employs a qualitative approach informed by a narrative design that integrates the stories of Black male teachers, school leaders, and university teacher educators in the recruitment, support, and retention of Black male teachers. Through fictional narrative, I will restory the experiences of Black male teachers to highlight where critical caring and support from leadership can sustain Black male teaching trajectories.