This paper presents our clinical experience with patients who were severely traumatized by the systematic violation of human rights during the military dictatorship in Chile (1973–1990). The lack of recognition of trauma of sociopolitical origin encapsulates the traumatic experience and forces it to remain as part of the present. Clinical vignettes of two therapeutic processes—mother and son—are presented: The mother was detained; sexually tortured; and, as a result of this, gave birth to the torturer’s son. Her therapeutic process is an account of her ambivalence towards her son, of how his origins were kept a family secret, and of how this secret was unconsciously transmitted. The young man’s therapeutic process centers on the transgenerational transmission of trauma and how the torturer–tortured dynamic seeps into the relationship with the analyst. The impact on the analysts’ subjectivity in working with extreme trauma is described.