School-Wide Positive Behavioral Interventions and Supports (SWPBIS) is a school disciplinary framework seen as an effective tool to replace school disciplinary practices that contribute to the school to prison pipeline (STPP). While evidence suggests that SWPBIS can help improve school discipline and lower suspension/expulsion rates, it has not been shown to consistently decrease racial disciplinary disparities. This study thematically analyzed semi-structured interviews of educational staff at one high school at the outset of SWPBIS implementation to understand their perceptions of school discipline and the potential for SWPBIS to address root causes of racial disciplinary disproportionality. Using a critical race theory analytical lens to center issues of race and racism, the findings revealed a school that is deeply structured in Whiteness. Participants described the school as “two schools in one”—one that is largely White, affluent, and high-achieving and another that is predominantly Black, economically disadvantaged, and achieving at lower levels. Educators were open to key elements of SWPBIS, such as positive discipline and school-wide consistency in disciplinary practices. And while many participants identified systemic barriers to achieving equity, they simultaneously relied on discursive strategies that upheld Whiteness. These findings suggest that SWPBIS has the potential to be an alternative to punitive school discipline, but faces multiple barriers in addressing disciplinary disproportionality. The segregated and stratified school structure raises questions about whom SWPBIS is for and who will bear the burden of implementation.