Context: Ongoing teacher diversity campaigns will not increase the net number of teachers of color if policymakers fail to address the disproportionate rate at which teachers of color leave the profession when compared to White teachers. Purpose: The purpose of this article is to fill the empirical gap about the mechanisms that influence Black male teacher turnover. Specifically, this study explores the perceived school-based experiences of Black male teachers, with particular attention to comparing the experiences of Black men who are the only Black male teachers in their schools to those of Black men in schools with multiple Black male teachers. Research Questions: 1. In what ways do the school-based experiences differ for Loners (Black male teachers in schools employing only one Black male teacher) versus Groupers (Black male teachers in schools with larger numbers of Black male teachers)? 2. How does a school's organizational context, such as relationships with colleagues and school administration, affect the decisions of Loners and Groupers to stay in their schools or in the teaching profession? Research Design: This study employed a qualitative method, phenomenology. Two waves of semistructured in-depth interviews were conducted with Black male teachers(N = 27) across 14 schools. Seven schools had three or more Black male teachers on the faculty (n = 20), and seven schools had one Black male teacher on the faculty (n = 7). Each semistructured interview lasted approximately 60 minutes. Findings/Results: Groupers cited challenging working conditions (such as weak administrative leadership) as their primary reason for wanting to leave. The following academic year, almost half of these teachers (9 out of 20) did not return to their schools in the positions they had held the previous year. Counterintuitively, Loners, despite sometimes having hostile interactions with their White colleagues, stayed. While Simon and Johnson (2015) theorized that the absence of positive collegial relationships increases turnover, this phenomenon proved less true for Loners' decisions to remain at their schools. Recommendations: Given that Groupers were more likely to leave when compared to Loners, policymakers who are interested in increasing the number of Black male teachers must also give attention to retention. Future research should compare the school-based experiences and influences of turnover of Black male Loners and Groupers to other ethnoracial minorities, such as Latinx and Asian teachers. Practitioners, or specifically principals, may also want to become more attentive to interpersonal relationships in schools, particularly between Black male teachers and their White colleagues.