Chapter 2 analyzes a case study from Oprah Winfrey. Winfrey has always occupied a unique, exceptional, and almost superhuman position in the American cultural imaginary. Winfrey has long since abandoned the status of mere mortal in the eyes of fans and foes alike. In her ubiquity, Winfrey did much to not only shore up her own brand, but also configure the representational space of a particular brand of celebrity African American womanhood. That particular brand was strategic ambiguity. This chapter asks: what happened when the magic trick stopped working, or when Winfrey’s postracial, strategically ambiguous negotiations of race and gender weren’t successful? In this chapter, Joseph analyzes the limits of Winfrey’s so-called racial transcendence, considering a telling moment when she used strategic ambiguity but was still pilloried in the press as a race-baiting, uppity, Angry Black Woman.