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School leaders as moral agents develop moral literacy for ethical decision-making. These decisions often involve power, prejudice, pride, and personal preferences. The morally literate leader acknowledges these feelings and knows to move out of the range of these distracting forces. In this multiple case study analysis, the researchers present and compare two distinct but related cases of ethical dilemmas concerning teacher evaluation. In these quintains, we examine principals that faced dilemmas when in situations that required them to make controversial decisions that involved long-time and loyal teachers and following state mandates relating to teacher performance.