The author draws from critical Whiteness studies and the sociological imagination to show how three White preservice teachers in an urban education program used personal experiences with racial privilege to understand structural racism. These stories depart from portrayals of race-evasive White teachers who struggle to engage with critical perspectives on race and racism. The participants’ stories—which openly critique meritocracy and color blindness—not only demonstrate possibility, but they also raise concerns about the use of personal experience by dominant groups and note how considerations of White privilege do not necessarily lead to an understanding of how one is complicit in the reproduction of White supremacy.