This report synthesizes philosophical and psychological analyses to examine the recurring archetype of the aberrant leader throughout history. It begins by exploring classical Greek thought, particularly Plato's concept of the tyrant arising from democratic decay and Aristotle's analysis of the demagogue's tactics. The text then shifts to Machiavelli's pragmatic perspective, where traits like cunning and theatricality are reframed as necessary for maintaining power, though a truly Machiavellian prince must be calculating rather than impulsive or short-sighted. Finally, modern psychological frameworks, including narcissism, authoritarianism, and the Dark Triad, provide clinical explanations for traits such as combativeness, polarizing rhetoric, and ignorance, ultimately demonstrating the consistent patterns of this leadership style across different eras and contexts. Research done with the help of artificial intelligence, and presented by two AI-generated hosts.