Although psychoanalytic insights have garnered some recognition in the criminal law, they have also encountered significant resistance. For instance, psychoanalysis has illuminated the prevalence and potency of guilt in psychic life, an insight that would seem germane to criminal processes intent on adjudicating culpability for antisocial behavior. Yet the psychoanalytic view of guilt potentially challenges the efficacy and legitimacy of legal mechanisms. This essay contemplates the question of interdisciplinary work in law and psychoanalysis by analyzing certain rare instances in American jurisprudence where courts have attempted to grapple with psychoanalytic understandings of guilt and the desire for punishment. These cases dramatize the deep tensions that exist between psychoanalytic and legal conceptions of human agency, tensions that also plague the efforts of psychoanalytically oriented reformers to revolutionize a penal system intent on punitive regulation.