In this paper, I describe the academic dilemma experienced by Tamara (pseudonym), a mathematically high-achieving high school sophomore. Raised in an economically strapped neighborhood, Tamara had the opportunity to attend a prestigious private high school, tuition free. Confronted by being viewed as an affirmative action student Tamara uses this negative stereotype as an extra source of motivation to achieve high marks on the admissions test. A new framework explains Tamara’s reaction to this situation that I call stereotype management (McGee & Martin, 2011b). Stereotype management describes the range of strategies and various forms of individual agency that high-achieving Black students employ to reduce the academic impact of demeaning stereotypes while maintaining high standards of achievement. For Tamara, however, her high test score and ability to achieve in the face of being stereotyped was bittersweet, as she examined the potency and permanence of being perceived as less than.