The structure of a society is the sum of the different kinds of agency different kinds of people exercise. Here we tell a story of the rise of the current intrigue-riddled, paranoid state of the world by examining the roles played by four individuals. Each is a case study in a distinct political personality. One, Noel Field, who we will call the Idealist: a pious Quaker activist whose naivete entangled him in a plot that got a truly astonishing number of people tortured and killed. Two, C. Wright Mills, who we will call the Renegade: a motorcycle-riding sociologist whose 1956 book The Power Elite informed subsequent revolutionary movements. Three, John F. Kennedy, who we will call the Celebrity: a man who was no stranger to Dark Triad traits, but who lacked the monumental propensity for deception of his rivals in the national security establishment. Four, Allen Dulles, who we will call the Councilor: a man who lacked the charisma of true celebrity, but who ultimately succeeded in his power struggle with Kennedy. We examine how people with extreme psychologies can often outmode others because of their very rarity, enabling them to concoct strategies no one sees coming. And, using cross-species comparison, we see how psychological traits vary so massively in part because there really is no evolutionary optimum, contradicting the idea of species-typical psychology—and by extension, species-typical social structure.