Teachers do not often have opportunities to openly examine and discuss issues of racism, power, and white privilege. In fact, as Lisa Delpit and other educators have pointed out, these discussions are systematically “silenced” in most educational discourse among teachers. This article explores why it is so difficult to have an open, explicit dialogue about power, privilege, and racism. We examine an instance in which there was a structured effort to hold such a discussion among 60 teachers during a professional development institute. Using discourse analysis and other methods derived from sociolinguistics and qualitative educational research, we focus on two central questions: (1) To what extent were the participants in this session able to have a discussion about racism, power, and white privilege? (2) What impeded and facilitated this discussion? The results will be helpful to anyone who might facilitate or plan discussions that focus on racism, power, and white privilege in education.