This dissertation addresses the question of which factors shape outcomes in autocratic regimes, and, in turn, what influences the survival of democratic regimes in light of their authoritarian legacies. I argue that regimes which are able to curtail the dictator’s powers, compared to uncontested autocracies, are associated with better institutional and socio-economic outcomes during the authoritarian rule as well as a higher survival rate upon transition to democracy. The first two papers of this dissertation provide evidence that regimes where the leader’s power is constrained either by an organised opposition or by a strong regime party are more likely to have an independent judiciary and experience higher levels of health expenditure. A third paper provides evidence that the mechanisms which protect contested autocracies also lay the foundation for an institutional framework in which the subsequent democratic regimes are more likely to survive. This dissertation offers a mixed-methods approach to confirm the three arguments. In conclusion, only with checks and balances in place, those in power can stay humble, take care of people, and promote good governance, compared to the ruler with unlimited power.