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Since Rice's (1963) seminal work on management, it has become axiomatic that the two critical tasks of leadership are protecting the boundaries of, and generating resources for, the organization or the enterprise which is led. However, the gradual decline of legitimate authority (Schaar, 1970) and the more recent and dramatic downward revision of institutional primacy, have complicated these tasks. When the human factor, in the form of personality style, character, and psychological motivation, is added to the leadership equation, then even systematic thinking and theory building about the topic are difficult. Not the least of these difficulties emanates from the large differences between the language of personality and that of social systems and organizational theory. In addition, much of the psychological contract that an individual makes with his or her organization is unconscious, and many of the expectations of an organization of its members are unspoken. Therefore, issues of irrationality, strain, and dysfunction within the individual and between the individual and the organization are at least as complex as those in any relationship or in any group. Since the fundamental premises of psychoanalysis are subject to debate within the field itself, a study that attempts to go beyond the field is subject to double jeopardy.