This article focuses on the intergenerational transmission of pathology, caused by tenacious parent/child bonds impeding normal separation and age-appropriate attachments in late adolescence. The case presented illustrates the impact of dysfunctional parenting approaches that have arisen from significant parental pathology. The adolescent son is arrested in development and suffers low self-esteem, an impostor false self, and long-standing, profound academic failure. A therapeutic model that combines elements of psychoanalytic psychotherapy and family therapy is described in detail, with particular emphasis on the contribution this model made both to the assessment and successful treatment of this adolescent boy and his family over a six-year period. A psychoanalytic individual psychotherapy and family therapy perspective are offered, to clarify the assessment and successful treatment process over six years of treatment.