This chapter discusses shared trauma and loss in the context of the devastating effects of political violence and terror, more precisely in relation to the Chilean dictatorship that followed the overthrow of the Allende government in 1973 and came to an end in 1990. It focuses on a play, Death and the Maiden, by the Argentinean-born playwright Ariel Dorfman. The play takes place at a time of transition in a country that "has given itself a democratic government after a long period of dictatorship". The chapter aims to explores the play from within and to extract from it themes that can deepen our understanding of processes contributing to a traumatic reaction and possible ways of coming to terms with it. It presents a psychoanalytic relational perspective on trauma and explores the play by discussing the views developed by American psychoanalyst Doris Brothers who defines trauma as the destruction of relational systems and of the certainties that shape psychological life.