Contemporary activists and scholars have framed how Black males are faced with constant policing and killing of Black bodies by White police officers (Coates, 2015) and how Black boys are being sent to punishment rooms in urban schools (Ferguson, 2000). Therefore it is not surprising that teaching in our politically and racially charged times can be daunting for both a White male teacher and Black boys in an urban school. Unnerving statistics about Black students reveal they are performing behind their White peers. Blacks are more likely to be expelled from school, and they are twice as likely to drop out of school as their White counterparts (Aud et al., 2010). However, there are teachers who are applying culturally relevant teaching (CRT) and who are mindful of students' funds of knowledge and cultural backgrounds. Because the majority of teachers are White, there have been calls for a study in which a White teacher used CRT to develop and focus on relationships with Black students to strengthen instruction. Data sources for this study included: (1) observations of classroom literacy instruction; (2) informal interviews with the focal teacher; and (3) 200 artifacts of pictures and copies of student work and instructional materials. The findings reveal that teacher-student relationships are pivotal in students' academic learning. Although the analysis is limited to a small case study of one classroom, the relationships presented should encourage mainstream White teachers who are outsiders to minority students' cultures to implement CRT.