This chapter examines pathological hope based on a defensive grievance organisation and explores the intrapsychic obstacles to the patient’s experiencing and accepting loss as loss and the past as past. It considers the hypothesis that the patient’s belief in the transference, her conviction that her therapist could be her mother, is a primary obstacle to the mourning process and that this derives from the patient’s experience of unconsciously living life as a transference object for a troubled parent. D. W. Winnicott considered delinquency to be a sign of hope, at least delinquency in its original form, when the delinquent act of the child was meant to call to the attention of a potentially responsive parent that the child was feeling hurt or deprived. Winnicott described two broad categories of delinquency: stealing, which he related to maternal deprivation, and aggression, which he related to paternal deprivation.