Although there is no more iconic, stalwart, and eloquent defender of liberty and representative democracy than J.S. Mill, he sometimes endorses non-democratic forms of governance. This article explains the reasons behind this seeming aberration and shows that Mill actually has complex and nuanced views of the transition from non-democratic to democratic government, including the comprehensive and parallel material, cultural, institutional, and character reforms that must occur, and the mechanism by which they will be enacted. Namely, an enlightened despot must cultivate (...) democratic virtues such as obedience, industriousness, spirit of nationality, and resistance to tyranny in the population and simultaneously prepare the way for his own demise and secure his own legitimacy by transitioning to the rule of law. This challenges recent scholarship that paints Mill’s non-democratic views as crudely and uncritically imperialist, because it fails to recognize and engage seriously with his sophisticated (if ultimately problematic) theory of individual and institutional development under enlightened colonialism. (shrink)