This article discusses why the theme of exile, marginality and the role of outsiders occupied Judith N. Shklar and how it impacted on her teaching and writing. More specifically it draws on Shklar’s last Harvard lectures and essays in which she reflects systematically on the questions of obligation and exile. It maintains that the relatively late turn towards exile is neither accident nor retrospective construction. Throughout her adult life Judith Shklar argued from a position of ‘optimal marginality’ – what has been called ‘exile from exile’ – that allowed her to situate and present herself simultaneously as an outsider and to present her political theory as a kind of pedagogic and maieutic discourse. This was a way of turning traumatic personal experiences into a creative academic performance marked by true intellectual curiosity.