In this 6-year longitudinal interpretative case study, the researcher examined four white elementary teachers’ beliefs and practices related to teaching race. Interview, observation, and classroom artefact data were collected from their teacher preparation program through their fifth year in the classroom. Using critical race theory and critical whiteness as the lens, the researcher found: (1) A division exists between tolerance- and equity-oriented teachers. (2) While two teachers had relatively fixed orientations, two teachers shifted their orientations over time; these shifts related to their school culture and their professional development opportunities. (3) The teachers were more likely to teach about race in schools where they had dedicated time for social studies. This study revealed the influence that teacher preparation and school context had on the white teachers’ development in teaching about race. This study also drew connections between teacher preparation programs and race-related practices during the teachers’ beginning years.