Principal Harris, a new Black male principal at Merion High School, has found himself under fire for allegedly promoting critical race theory (CRT). He has received several forms of pushback as he navigates district and state mandates, racial trauma, invisible taxes, and microaggressions. Unfortunately, his best intentions are not good enough. This case is designed to display the various factors Black principals face in schools and districts amid ongoing public health crises (e.g., COVID-19 and racism). I describe the layered role of race, racism, and racial trauma on Principal Harris through his reflections and responses to stakeholders.