Vice Presidents of Student Affairs (VPSAs) lead in a context nuanced around race that conflicts with their duty to enact the student affairs profession's espoused values of social justice and inclusion. This paper summarizes findings from a critical qualitative case study conducted with 10 VPSAs from a diverse group of institutions located in the southeastern region of the U.S. The findings reveal how VPSAs straddle the line between prioritizing student success for students of color and serving their historically exclusive institutions. [Note: The issue number (2) displayed on the first page of the PDF is incorrect. The correct issue number for this article is n3.]