Purpose: The purpose of this study is to evaluate factors that contribute to black male school leaders’ career progression and sustenance within the teaching profession. This, because the progression of black and minority ethnic (BME) teachers in Britain has been the subject of much debate. Fewer BME teachers are in leadership roles in education, and there are only 230 BME headteachers of approximately 24,000 primary and secondary headteachers. Design/methodology/approach: The headteachers’ professional lives are explored through the lenses of critical race theory and interpretivism. In doing so, it illuminates the journey towards and the realities of a group whose views are currently unrepresented in research on school leadership or that of the experiences of male BME teachers in England. Findings: This study finds that whereas personal agency and determination are largely responsible for keeping these black headteachers in post, “White sanction” (Miller, 2016) has played a significant role in career entry and early career development. Furthermore, participants experience both limiting and facilitating structures as they negotiated their roles into headship and as headteachers. Limiting structures are those which constrain or hinder progression into leadership, whilst facilitating structures enabled participants to navigate and negotiate gendered racism, make progress in their careers and achieve success in their respective roles. Both limiting and facilitating structures include personal agency and contextual factors. Research limitations/implications: The paper also makes the point that more research is needed on current BME school leaders to examine the factors that motivate and enable them. Additionally, more research is needed on the limiting and facilitating structures identified in this study and on the potential generational differences that may exist between more established and newly appointed male BME school leaders. Studying generationally different school leaders may help to illuminate the salience of race and racism across an increasingly diverse population. Practical implications: Furthermore, this paper also suggests that more BME school leaders are needed, thereby making the leadership teams of schools more representative, as well as raising aspirations and interest among BME teachers and therefore making black leadership sustainable. Originality/value: This paper is an original piece of research that adds fresh insights into not only how black school leaders get into teaching and leadership but also significantly what keeps them there.