Narcissistic Personality Disorder is considered to be one of the most tenacious and stable types of personality organization. It usually presents a challenge to clinicians and is often resistant to treatment. The continuous search for the affirmation by others of the grandiose self and the devaluation of others in an attempt to stabilize their self-esteem is typically seen in individuals with narcissistic personality organization. On the other hand, corrective life events such as personal achievements, long-term nurturing relationships, and the management of loss and disillusionment can contribute to a more realistic realignment of the person's Ego Ideals and self-esteem. One such example is the case of Don Joaquin, a 69-year-old playboy who was facing death from leukemia. This article will describe the supportive and psychodynamic psychotherapy treatment approach that was utilized, and how Self-Psychology and Object Relations Theory provided a useful framework to bring help and relief to this patient, as he prepared to face the end of his life.