This paper explores the psychoanalytic concept of the Oedipus conflict as representing ambivalent and fragile tensions between generations. While the Oedipal conflict typically refers to the young child’s ambivalent feelings towards the parents, here I consider how Oedipus is reprised in adolescence with respect to markers of history. The paper considers the unconscious uses of historical representation in the making of a self and suggests why teens can be so ready to dismiss the past, sometimes toying with its destruction. The analysis is grounded in a current event that the author reads as, “an Oedipus for our time,” and that gives rise to the difficult question of generational conflict for history education.