Transformative work with teacher candidates relies on a critique of the tenets of Critical Pedagogy and subsequent Critical Whiteness Studies (CWS). I employ analyses of extant scholarship to argue that these specific domains, as popularly framed, might be responsible for uncritical examinations of the White teacher education students who devotedly enroll in our courses and trust their teachers to treat them fairly, responsibly, and with care. I then entwine relevant research on White privilege pedagogies with my own narrative to argue that taking on the problem of Whiteness in teacher education seems to have inspired an uncritical pedagogy of harmful generalizations. To conclude, I reconceptualize the application of White privilege pedagogies for more complex, systemic examination, and argue that if we are to move beyond a pedagogy of dismantling students, more work which openly and honestly grapples with paradoxes, double binds, and contexts of Whiteness is needed.