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A detailed account of the history, dynamics, and treatments of a chronically and severely troubled man and his eleven-year-old son is presented. This was the father's first experience of psychoanalytic psychotherapy; he had previously undergone four courses of supportive therapy. Father and son were enmeshed in intense maternal dyadic relationships that prevented their developing adequate paternal and masculine identifications. The father's resistance to therapy and to the development of a useful paternal transference was not resolved until his son entered therapy. The authors decided to collaborate by discussing their respective cases with one another. The article discusses the potential transference and countertransference difficulties of such a course of action. The authors believe it enhanced their understanding of the interlocking pathology and facilitated the separation and growth of father, son, and mother, which is depicted as the authors describe transference reactions and their management, family interactions, identity formation, and conflict resolution. At some point the mother also sought therapy for herself.