This article examines the teaching philosophies of Black male teachers of Black male students in manhood development classes in a district-wide program in Oakland, California. Drawing on observations and instructor interview data, we explore the teachers' histories, teaching philosophies, and the trajectory of their racial-educational understandings. We utilize Gramsci's (1971) theory of the organic intellectual, Mills' (1997) and Leonardo's (2013) theories of the subperson and substudent, and Dumas' (2014) notion of Black suffering to theorize the ways that race comes into play in the teaching of African American male students. We find that racialization and re-humanization are key to instructors' teaching, and we identify two key aspects of their teaching philosophies: (1) Humanization/Love and (2) Reciprocity.