This chapter offers a more detailed presentation of the problem of whiteness by exploring the nature of Americans’ long-standing opposition to race-conscious policy and Black reparations in particular. I identify a range of attempts by social scientists and empirically minded social theorists to interpret that opposition (through concepts like racial resentment, the white racial frame, white ignorance, and white fragility), and consider some specific cognitive mechanisms and strategies that help sustain it (including denial, misinterpretation, and emotional defensiveness/reactivity). For some, these obstacles establish that the fight for Black reparations, even if morally justified, is a non-starter politically and should be abandoned—a position I call quietism. I argue that the quietist conclusion is too quick, and advocate for the tactical re-orientation of at least some reparations discourse around the phenomenon of structural white advantage, defending this approach by appeal to some more recent empirical literature on privileged identity management. The idea is to incrementally sensitize white Americans to the reality of structural ingroup benefiting in a way that enables them to retain a grip on their personal and collective esteem by embracing the work of dismantling the various systems that afford those advantages.