Blood spilling into the streets in Charlottesville in August 2017 during a "Unite the Right" white supremacist rally, an August 2019 murderous rampage targeting Latinos at a Walmart in El Paso, Texas, and the most recent January 2021 storming of the U.S. Capitol represent only a few of the violent events that have occurred in the past 5 years initiated by far-right white supremacists. Fringe and violent behaviors do not exist in a vacuum. Every day, privileged white folks adhere to hegemonic ideals and engage in racist transgressions that stoke the fires of extreme violence. Significantly, however, some members of the privileged class eventually reject racist ideology and emerge as activists for marginalized populations. Drawing on the theoretical frameworks of Pedagogy for the Privileged, Pedagogy of the Oppressed, Transformative Learning Theory, and Critical Whiteness Studies, this paper asks the question: What facilitates a significant ideological shift?