This paper takes up the themes of organization as dreamscape, the psychodynamics of everyday organizational performance and organizational rituals and the enactment of death and desire in the context of a longitudinal case study of an academic institution. This case study focuses on the various ways in which the organization has developed and continues to develop neurotic and dysfunctional tendencies. It looks at the ways in which those tendencies are expressed in the culture and structure of the organization and the ways in which the various constituencies of the college are complicit in the enactment of the neurosis of its leadership, as reflected in various dependent and counterdependent dynamics and performances. Of specific interest in this paper are the changes in neurotic patterns over time and the ways in which these changes relate to the changes in leadership. Using Kets de Vries' concepts related to organizational neurosis, we will discuss how the college moved from a compulsive organization to a dramatic organization.