Like many classroom teachers, I long understood antiracist pedagogy as white privilege pedagogy (McIntosh, 1988), where students must confess to their privilege to embrace antiracism. By leaving young white people with untenable models of understanding themselves as raced beings, this work has, to put it generously, come up short. Using critical ethnographic methods, I seek to make better sense of these sincere shortcomings by locating them in historical (Allen, 2012; Roediger, 1991) and emotional (Boler, 1999; Trainor, 2008; Zembylas, 2006) contexts. I worked with ten white high school students over the final five months of their senior year. We attempted to work through the constrained and paradoxical ways they understood race and race talk. We worked through their struggles with the languages and patterns of race talk, their inadequate schooling on race, and their inability to manifest their antiracist values. I find that the discourses available to them, in particular white privilege pedagogy, limit their capacity to both imagine themselves as antiracist actors and take up antiracist actions. I suggest that by examining and unpacking the discursive binds attendant to their race talk (Pollock, 2004), and by making visible the historical and emotional contexts of their understandings of themselves as raced beings, educators can more effectively guide young white people toward antiracism.