Sophocles's Philoctetes (409 BCE) is a dramatic masterpiece unfamiliar to most analysts. The play presents a complex portrait of self-injurious spite of heroic dimensions as it touches on issues of intense shame, feelings of helplessness and the refusal of forgiveness. Sophocles's protagonist, Philoctetes, is a man who, like some of our patients, refuses to be healed. He intends, through his continued sickness and misery, to exact revenge against those who mistreated him. These are recognizable clinical issues, playing roles in every psychoanalytic treatment, issues that may assume a special importance in protracted, stalemated or aborted analyses. There are patients who damage the analyst by damaging the analysis they are in, a malevolent project often undertaken in revenge for wrongs suffered during childhood. This paper links Sophocles's drama to these vitally important clinical considerations through the discussion of a particular case.