Most private schools in the United States have a history of racialized segregation. Despite this, families from historically oppressed backgrounds often choose to navigate private schools for the academic and social benefits they promise. As diversifying institutions, private schools must attend to how the unique context of private funding changes how they engage with meaningful racial equity work. The article uses a case study of one traditional, private school to investigate (1) its patterns of racial discrimination and (2) how/if the school enables or disrupts those patterns. The analysis found primary patterns of racial discrimination at both the interpersonal and institutional level. Stakeholders most frequently identified racial discrimination through isolation, overt racism during sports, and racially discriminatory dress code enforcement. The analysis also found the school was willing to engage in meaningful racial equity work if and only if it also aligned with the school's public image and the priorities of the major donors and legacy families.