Background/Context The link between care and teaching is well accepted, and positive teacher-student relationships are known to benefit students’ in-school experiences and academic success. Yet, positive teacher-student relationships are not the norm for African American males and African American male students’ experiences and performance in schools remains an issue. Purpose/Objective/Research Question/Focus of Study What characterizes the teacher–student relationships within the all-Black, all-male classes of this district-sponsored program? Moreover, how do the instructors for the program enact these characteristics in their classrooms? Setting This study examines a project of the Office of African American Male Achievement in Oakland, CA. The Manhood Development Program was an elective class in the high schools and an after school program at the middle schools that sought to improve Black male students’ academic success and school experiences, and teach students about their cultural and community histories. MDP classes were offered to Black male students and taught by Black male educators. Population/Participants/Subjects Based on support from and communication with the MDP facilitators and school administrators, the participants in this study include MDP instructors and their students at three high schools and one middle school within an urban school district where there are persistent, racialized disparities in rates of discipline and in levels of academic success. Research Design This article reports on a qualitative case study of the teacher–student relationships within four classrooms that were part of a program for African American male adolescents within an urban school district. Data Collection and Analysis During one academic year, four of the MDP classes were observed at least four times and videotaped at least twice. Interviews were completed with three of the class instructors and with 41% of students across the four classes. The observations and videos were analyzed for instances when teacher–student relationships were leveraged towards specific pedagogical ends. Micro-ethnographic analyses were conducted of the video instances to highlight the dimensions of caring exhibited in the teacher–student interactions. From these analyses, one interactional segment was chosen to illustrate the existence and nuances of a politically intentional form of caring. Findings/Results The MDP instructors’ sociopolitical consciousness impacts and shapes their relationships with their MDP students. MDP instructors articulate and enact specific goals around how to construct caring teacher–student relationships that stem from their intention to positively influence the lives of Black children, push back against the racialized and hegemonic institutional structure of schools. MDP instructors teach in a way that is fundamentally connected to the local community in Oakland and make a concerted effort to know, rather than stereotype, each student and to develop each students’ full potential. These relationships are intentional, political, and visible acts of care by MDP instructors that are interactionally coconstructed within their classrooms. Conclusions/Recommendations This case of politicized caring questions the premise that education and schools are, and should be, narrowly focused on developing test preparation, career-readiness, or content-specific practices. Instead, this case illustrates the alternative educational ideologies and practices of four Black educators that allow them to reclaim their social and political responsibilities and create effective, nurturing, antiracist schooling environments for Black students. This microanalysis of one of these classes offers an example of a type of caring and pedagogy that currently exists and that could be more widely available to Black students.