This paper presents an applied psychoanalytic study of Eugene O'Neill's two-character play, Hughie. Applying the constructs of self psychology, the play illustrates both the narcissistic features and the emotional and behavioral characteristics of compulsive gamblers. The study focuses particular attention on the role of narcissistic fantasies—with both grandiose and megalomaniacal features—in affecting, temporarily, the mood of the characters. Moreover, it is shown that a shared gambling fantasy—a “winner among winners”—enables them to experience a sense of camaraderie, humanness, and the illusion of kinship.