The topic of affirmative action has been a subject of intense debate, with both proponents and opponents offering compelling arguments. Justice Clarence Thomas, an associate justice of the U.S. Supreme Court, has consistently expressed strong reservations about affirmative-action policies, viewing them as a form of reverse discrimination that may "hinder the principles of meritocracy and equal treatment under the law." However, it is crucial to examine the personalized experiences and consider the nuances, such as underrepresentation and microaggressions, that surround affirmative action. This study utilizes a symbolic interactionist and phenomenological approach that pulls from the individualized/collective experiences of Black students/faculty at historically White colleges and universities (HWCUs) and examines their sociocultural experiences on campus. Findings from this study highlight the continuing discriminative practices and "peer to peer" interactions that Black students/faculty must navigate at HWCUs and the strategies utilized to circumvent mistreatment and institutional adversities. Data from this study provide more context for the ongoing conversation pertaining to affirmative action, "peer to peer," and institutional discrimination that Black students and faculty experience at HWCUs. In this article, I examine the concept of "leveraging tokenism," a strategy that Black students and faculty utilize to circumvent underrepresentation and racial microaggressions.