This chapter reflects on the gravitational pulls of white supremacist patriarchal imperialist capitalism that compel people, particularly those most privileged within the systems, toward a callous disregard of the pain and suffering of others in order to accept and assimilate into the hegemonic normative systems of power. Drawing on the author’s experiences of teaching in a historically and predominantly white academic institution, this chapter reflects on pedagogical practices of disrupting the whiteness of callous disregard. This requires the building of classroom communities that can hold a compassionate awareness of students’ differential relationships to and experiences of interlocking systems of oppression and violence. In this essay, I share some of my experiences in and outside of the classroom with seeking to disrupt and undermine the distanced and disembodied approach to racism, white supremacy, and other forms of oppression. I offer some of the methods and strategies I am learning, and try to practice, that encourage myself and others to name, understand, explore, and begin to heal from trauma and violence caused by historically-based interlocking systems of oppression.