My aim in this chapter is to reflect on psychopathy in connection with personal identity to achieve clarity with respect to that condition’s potential for medicalization. Given plausible (if theoretically thin) accounts of psychopathy, personal identity, and medicalization, I consider the question whether psychopathy is amenable to medicalization. I argue that, not only is psychopathy not in fact amenable to medicalization, it is not amenable to medicalization even in principle. In the jargon of contemporary analytic philosophy, the medicalization of psychopathy is not “logically” or “metaphysically” possible. Importantly, the operative notion of medicalization reflects contemporary Western society’s conception of medicine, a conception which is subject to change, given relevant changes in that society’s understanding of the scope and limits of medicine proper. It is possible that, given conceptual changes of the relevant sort, psychopathy might prove amenable, at least in principle, to medicalization. For this to occur, society would have to adopt a new and radically different conception of medicine, one broadened so as to include, not only the treatment of patients suffering from disease (illness, or disorder) but also the transformation of patients (psychopaths) into literally different, or “numerically distinct,” persons (non-psychopaths). However, given today’s societal conception of medicine, which emphatically does not include the transformation, moral or otherwise, of patients into literally different (or numerically distinct) persons, psychopathy is not amenable to medicalization even in principle. It would thus be false, or at the very least misleading, to claim today that psychopathy might “someday” be medicalized.