Many elite schools proclaim a commitment to racial and other aspects of student diversity and inclusion. Pursuing this commitment is highly complex and contentious given the traditions of exclusion elite schools are founded upon. This paper examines some of these contentions drawing on research conducted at Cherry Tree Academy, an elite pre-K-12 school situated in the USA. Interviews and observations with faculty and students revealed contentions related to race at the school. Diversity efforts were considered synonymous with addressing the needs of Black students and produced expressions of apathy and victimhood from majority White students. Such racial contentions are examined in relation to the concepts of meritocracy and social justice. Examining these contentions remains significant in light of the renewed commitment to diversity and inclusion in elite schools and the reality that elite students are likely to be tomorrows' decision makers with the power to create more equitable societies.