The "millennial" historical moment presents fresh dilemmas for race-critical instructors. In addition to being well-versed in colorblind racial discourse, millennial students are socialized in a pop-cultural milieu that implies a more integrated, racially egalitarian world than exists in reality and includes claims that U.S. society is now "post-racial." Millennials" enthusiastic consumption of race in an era of seeming progress leads them to assume an ever greater social distance between their generation and the relics of those they consider "real" racists, as well as between the former eras of "de jure" white supremacy and the more racially meritocratic structure they presume exists today. In light of such obstacles, race-critical instructors must employ creative strategies to help students understand and identify their connections to larger, structural matters that create and sustain racial inequality at the systemic level. I introduce one successful approach, where students examine the social reproduction of racial inequality by tracing their family histories of wealth and capital acquisition and transfer. (Contains 1 table and 1 note.)