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The arena of politics provides a natural environment for individuals with significant narcissistic personality traits, individuals who are consumed by dreams of glory. This article first reviews developmental pathways to the wounded self, using the example of Saddam Hussein, whose traumatic background led to the defensive adaptation of a fixated grandiose self. It also considers individuals who were raised to be special, such as President Woodrow Wilson and General Douglas MacArthur, and who were the vehicles of their parents’ success. The article then addresses the psychology of charismatic leader–follower relationships, where there is a natural fit between the mirror-hungry leader, seeking adulation, and his ideal-hungry followers, who feel incomplete unless they are attached to a great other. The chapter emphasizes the impaired interpersonal relationships of narcissistic characters, and how this can contribute to an imperfect evaluation of political reality, as the leadership circle tells the leader what he wants to hear rather than what he needs to hear.