Educators throughout the ages have offered metaphors and analogies for teaching and teachers. Prominent among them are: gardener, midwife, facilitator, guide, sacrament. Each of these metaphors shed light, from a different angle, on the act of teaching. This article proposes the metaphor of tragedy as a way of shedding new light, from a totally different perspective, on what it means to engage in academic teaching of religion. It explores three areas in particular in light of the metaphor: the quest for certainty, the confessional classroom, and learning without teaching. Tragedy holds the possibility of opening up awareness of the uniqueness of teaching the conversation when placed in critical dialogue with these three areas.