This case takes a close look at Agamemnon’s famous “test” in the Iliad, when he feigns defeatism in order to gauge the resolve of his people’s commitment to war (Iliad 2.1–485). While interpreters often see Agamemnon’s test as bad strategy and a failure, since his people do try to give up and go home, audiences often overlook that Agamemnon is also ‘testing’ his captains and their commitment to his leadership. This case study will use insights from modern cognitive studies in empathy and so-called “mind-reading” to re-position Agamemnon’s failure as a reflection on the complex and multi-directional nature of leadership in the face of steep odds and difficult conditions. Students will consider how leaders use empathy to “read”’ the minds and emotional states of their community and the extent to which communities are made up of multiple minds with divergent expectations and reactions. Students will be invited to analyze how Agamemnon’s actions may be judged from both the perspective of their immediate consequences and their long-term effects.