This research study was designed to examine how two White teachers trained in a traditional education program at a predominantly White institution experience their first year of teaching in predominantly Black schools. More specifically, the study seeks to explore the ways in which teachers’ biography, teacher training, and context impact their teaching practices. The study utilized the qualitative research methodology of case study. The researcher found that though the teachers felt that their university training and student teaching experiences did not fully prepare them for teaching in high-poverty, predominantly Black classrooms, the teaching contexts (the characteristics of their teaching environments) were most powerful in exerting influence on the teacher’s first year teaching experience. Furthermore, the opportunities that the teachers had to actualize their training were dependent on their contexts and their contexts were not equivalent. The study also revealed that though the teachers deeply cared about their students, they did not hold high academic expectations for them; thus, the teachers exemplified the deficit perspective. The deficit perspective (King, 1994; Ladson-Billings, 1994; Mitchell, 1998; Quiocho & Rios, 2000) does not assume the students’ potential, but aims to compensate for what is presumed missing from the students’ backgrounds (Foorman, Francis, & Fletcher, 1998). The study concludes with the claim that teacher training programs must commit to diversity throughout the curriculum and teacher training experiences by exposing students to multicultural education and diverse student teaching and practicum placements.