Clinical experience in the Personality Disorders Institute at Weill Cornell Medical College suggests that patients with borderline personality organization and a narcissistic personality disorder have a more serious prognosis than all other personality disorders functioning at the borderline level, and that those who in addition present significant antisocial behavior have an even worse prognosis (Clarkin, Yeomans, and Kernberg 1999; Stone 1990). This negative trend culminates in a group of practically untreatable patients with antisocial personality disorder, who represent the most severe cases of pathological narcissism. There are also patients with severe narcissistic personality disorder, functioning at an overt borderline level with significant antisocial features, but not presenting an antisocial personality disorder proper, who at times respond to treatment, while others do not. These patients are explored here, with a focus on particular psychotherapeutic techniques that have proven helpful, as well as on the limits of these technical approaches.