School discipline disparities for African American students in urban schools continue to be a topic of contention. While research has rightfully called into question the practices and preparation of teachers and principals, the role that assistant principals serve as disciplinary gatekeepers has gone relatively unnoticed in the literature. The purpose of this study was to explore the experiences of five assistant principals at two urban middle schools to ascertain how they addressed issues of race amid applying school discipline interventions for African American students. The findings are analyzed and discussed through a critical race theoretical framework.