This paper constructs an argument about the emotionally complicated and compromised learning spaces of teaching about anti-racism in higher education. These are spaces steeped in complex structures of feeling that evoke strong and often discomforting emotions on the part of both teachers and students. In particular, the author theorizes the notion of strategic empathy in the context of students' emotional resistance toward anti-racist work; he examines how strategic empathy can function as a valuable pedagogical tool that opens up affective spaces which might eventually disrupt the emotional roots of troubled knowledge--an admittedly long and difficult task. Undermining the emotional roots of troubled knowledge through strategic empathy ultimately aims at helping students integrate their troubled views into anti-racist and socially just perspectives. (Contains 1 note.)