Winnicott’s theory of transitional phenomena looks mainly at the normative experience of children’s early efforts to use proto-imaginative and bodily strategies to self-regulate in nonverbal dialogue with the parents. This paper explores another, less optimal possibility, one where the transitional object is shunted into a dissociated realm of experience under the weight of a deeply negative, grandiose co-constructed narrative. The enduring presence of that split-off, psychically impoverishing narrative can aggravate a vulnerability toward addictions and compulsions in adulthood, complicating the individual’s ability to make use of dominant addiction treatment models or the transitional space of the analytic relationship, as illustrated by the analysis of a patient struggling with a compulsive involvement with Internet pornography.