<p>There has been limited attempts to explore paradigms of educational leadership enacted by Black men. This study draws on previous substantive research to examine the ways in which context, as well as role of leadership identity, values, and culture, inform the leadership experiences of Black men in K-12 school principal or head of school leadership positions—principals and heads of school. The study adopts a qualitative phenomenological approach, use of online descriptive survey, in-depth semi-structured interviews and photo elicitation methods, with 14 Black male school leaders from across the United States, to provide structural and textural descriptions, synthesis of meanings and essence of the experience and phenomenon of Black male K-12 school principal and head of school leadership. The study highlights the range of challenges and demands of the principalship that contribute to the dearth in Black leadership. While situated in the context of educational leadership, viz. within a public, charter, independent, private, or faith-based school setting, the study has much applicability to the leadership experiences of Black men and women across the range of leadership to include education, non-profit, for-profit, and corporate leadership. The study further highlights the benefits of valuing the leadership paradigms of Black men, references to cultural traditions and customs, “frientoring”, mentoring, and social networks. The study concludes that culturally sensitive leadership development increases representation, lifting the voices and leadership approaches of Black leaders broadly, and Black men in particular. This expands the educational leadership canon of research and scholarship towards improved global paradigms, experience, practice, and [re]expression of the critical race conceptualization of educational leadership and leadership development.</p>