The concept of empathy in history education involves students in the attempt to think within the context of historical agents' particular predicaments. Tracing the concept's philosophical heritage to R. G. Collingwood's philosophy of history and "re-enactment doctrine", this article argues that our efforts in history classrooms to understand historical agents by their own standards are constrained by a tension that arises out of the need to disconnect ourselves from a present that provides the very means for understanding the past. Though rather than serving to undermine the concept, it is proposed that the moderate hermeneutics of H.-G. Gadamer, through a positive conception of prejudice, tradition and temporal distance, transforms the factors typically seen as inhibitors to empathy's operation into those that potentially enable it. The article aspires to shed new light on what is at play when history students engage in the intellectually demanding task of empathizing in history.