This article explores situations of interpersonal catastrophe during psychoanalytic psychotherapy with survivors of prolonged childhood abuse; situations of unbearable psychic pain focused on the therapeutic relationship, accompanied by functional deterioration, that is, mutual but not symmetrical. Through analyzing Orpheus’s failure to save his wife from the underworld, I look at the analyst’s unconscious motivation to treat others: What is drawing us to other people’s hell? I will describe how the analyst’s identification with the aggressor when facing the patients’ inability to mourn, as well as the patient’s own tendency to identify with the aggressor, may trap the therapy in a fantasy of rebirth or a wish to go back to the roots and correct or erase the trauma. In doing so, this may push the treatment into a malignant whirlpool. I explore the clinical manifestations of the mutual fantasy of overcoming the limits of reality and offer an analytic meaning to the concept of rehabilitation versus recovery that may be helpful in working with these challenging cases.