This paper offers a somewhat 'painful' reconsideration of the subject of masochism through a close rereading of the significant thinkers on the subject. In particular we will look at the specific manner in which Gilles Deleuze's work Coldness and Cruelty revitalizes scholarship for the subject and restructures the symbolic framework of psychoanalysis - whereby what is called masochism has come to be understood.  In what follows it will asked: Are we to read the sacrificial, self-abnegating nature of the masochist as weakness and self-destruction, as consequently a turning away from any attempts at its own particular mode of empowerment? Or does this conclusion deceive us and is it rather the case that the masochistic subject is nothing more than a great actor, disguising, as it were, its instincts towards the fulfillment of its peculiar mode of empowerment? In what sense are we certain that the masochist aims at discomfort, pain, submission? Is there really a reversal whereby what is painful becomes rather a source of pleasure? This paper argues that we ought to think of pleasure and pain within the masochist schema as not a simple reversal of aims, but rather as a means toward bringing into being its own particular mode of empowerment. Through a careful explication of the symbolic register said to be inherent to the masochist subject it will be questioned as to whether the masochist is as self-destructive as his behaviours, contracts and fantasies would have us believe. In doing so, it will be suggested that Deleuze himself, single-handedly opens up a path for a new form of scholarship on the subject.