The paper is narrowly addressed to a single puzzle: How did it happen that countries that attempted to install democracy earlier enjoyed it less frequently? Regime dynamics are driven by two mechanisms: (1) Democracies become more durable as per capita income increases, and (2) Past experiences with democracy destabilize both democracies and autocracies. As a result, countries that experiment with democracy at lower income levels experience more regime instability. Moreover, until they reach some income threshold, at any time such countries are less likely to be democratic than countries that first enter democracy when they have higher incomes. Hence, paradoxically, the resistance of European monarchies against democracy resulted in democracies that were more stable than those following postindependence attempts in Latin America.