In the 21st Century context of violent racial divides, dismantling racism in social work education requires deep trust that social transformation and healing is possible. “Wringing out the whitewash” metaphorically captures the heavy labor of interrupting the rigid Eurocentric epistemological hegemony undergirding the pedagogy, research, and praxis canons of social work. It requires rigorous attempts to unsettle and decenter entrenched white supremacist ideology, assumptions, and values. In this labor, we create space for the multiple identities and worldviews that students and professors occupy to reshape educational encounters. In this paper, we present our critical pedagogical approaches as Black social work educators committed to liberation and healing. We articulate how our positionalities as Black cisgender women at urban universities, one a Northeastern Historically Black College and University (HBCU) and another at a Northeastern public university, facilitate our intentions to honor truth-telling and intergenerational interdependence. We present differences and similarities in how we use assignments to disrupt the institutional reproduction of racism, provide solace for repair and healing, and re-center collective identity as strength. We present transdisciplinary frameworks shaping our pedagogical choices, namely historical trauma and urban womanist social work pedagogy. Implications for the future of social work education will be discussed.