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This article chronicles an extended psychoanalytic treatment of a bipolar gay man who suffered from unremitting suicidal depression, mania, paranoid psychosis, and psychic fragmentation due to severe complex trauma and developmental deficits in attachment and cohesive self-structure. Following his initial hospitalization within an inpatient psychiatric facility after a suicide attempt, I present his course of treatment in outpatient practice over a four-year period that highlights the psychodynamics of the case, the treatment parameters, and the multiple crises that led to chronic suicidality, re-hospitalization, manic psychosis, and an eventual incarceration in prison for criminal theft and fraud due to an unconscious death wish and need for self-punishment for being homosexual. In atypical clinical honesty, I discuss the various countertransference enactments I engaged in as I struggled with the treatment, such as encouraging the permeability of the treatment frame, offering unsolicited self-disclosure, visiting his house, running personal errands, taking him to the hospital, giving him a gift, precipitously accepting and returning phone calls, engaging in lengthy, ongoing email discussions, and letting the patient run up a large debt. It is for these reasons that it becomes instructive to consider just how far one should go in the name of therapy. Implications for clinical discourse in countertransference are discussed.