This essay begins with an ekphrastic object lesson: the description of a throw pillow on which an image of Freud psychoanalyzing Shakespeare has been printed is taken to exemplify a standing cultural assumption that the intimacy of these two author functions can be assumed as a readymade or a fait accompli. The author argues that this pillow exemplifies a “pillow problem”: the problem of an overly cozy and complacent assumption of connection which must in fact be challenged if the field of psychoanalytic Shakespeare criticism is to progress, and especially if it is to ask and answer new questions about both authors and their possible relations. The chapter proceeds to discuss the sequence of chapters in the edited collection to which it is an Afterword, suggesting that, in their pointedly new arguments and claims, the chapters offer a model for how to escape or transcend the pillow problem. The chapter ends by suggesting the need for engagement with early modern trans studies and premodern critical race studies if the field of psychoanalytic Shakespeare criticism is to escape the Pyrrhic victory of a too-easy hermeneutic success.