An ongoing structural problem for the normative political theory of punishment concerns the question of ‘just deserts in an unjust society’, explored here as the question of the guilt of the victim who victimises another. While political theory cannot justify punishment in such circumstances, the possibility of a moral and psychological sense of guilt still exists. This chapter juxtaposes liberal theory’s impasse with a moral psychology of guilt drawn from the psychoanalytic perspectives of Melanie Klein and Jessica Benjamin. Based on complex love and reparation, this account of guilt is an important way of understanding what is at stake in human violation. Classical political views of the impasse are explored in Kant and Hegel, while Antony Duff’s theory of punishment as communication is seen as seeking to go beyond these but remaining constrained by them. Klein’s account of guilt as a reparative emotion is linked to Benjamin’s ideas of the ‘doer’ and the ‘done to’ and the possibility of reconciliation through recognition. This deeper sense of guilt cannot cure the problem in political theory but shows how an alternative moral psychology of guilt is available even where such theory is exhausted.