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Against several recent interpretations, I argue in this paper that Immanuel Kant’s support for enlightened absolutism was a permanent feature of his political thought that fit comfortably within his larger philosophy, though he saw such rule as part of a transition to democratic self-government initiated by the absolute monarch himself. I support these contentions with (1) a detailed exegesis of Kant’s essay “What is Enlightenment?” (2) an argument that Kantian republicanism requires not merely a separation of powers but also a representative democratic legislature, and (3) a demonstration that each stage of a democratic transition can potentially be in an absolute monarch’s short-run self-interest. I conclude the paper by defending Kant’s theory of democratization against charges of consequentialism and paternalism and by pointing out its similarity to other accounts of democratic transitions (for example, those of Samuel Huntington and Guillermo O’Donnell), suggesting a previously unnoticed opportunity for cross-fertilization between political philosophy and comparative politics.