This case illustrates why school leaders must be culturally proficient to serve all students and lead effectively. I discuss one case in Ohio that is representative of many other American schools. In particular, I examine the cultural challenges educational leaders must commonly face. This case encourages administrators to participate in meaningful conversations with stakeholders to solve complex issues. The hope is to better understand how school leaders in diverse contexts can lead and embrace different cultures, beliefs, and norms. I also pose questions designed to prepare educational leaders for similar situations where they must address issues of culture.