This case examines the role emotional intelligence plays in a leader’s journey as they advance in a strictly hierarchical institution. We will follow the career of the 1st century CE Roman general and statesman Gnaeus Julius Agricola, who is most famous for securing the frontier province of Britannia for the Roman Empire. His son-in-law, the Roman historian Tacitus, wrote Agricola’s biography to be an example of a “good man under a bad emperor.” The case invites students to evaluate Agricola’s emotional intelligence in three contexts: his relationship with soldiers and leaders in the Roman army; his relationship with the provincial Britons he fought and ruled; and his relationship with the Roman emperors under whom he served, especially Domitian. Agricola’s actions will be classified and evaluated based on the emotional and social competency inventory (ESCI), a tool commonly used in modern business and organizational psychology contexts. Students will assess what forms of emotional intelligence Agricola demonstrated; what he gained from being an emotionally intelligent leader; and the ways in which his emotional intelligence fell short of what the situation required.