Why do some states embark on risky policies that appear certain to lead to disastrous outcomes while others seem more cautious as they interact with others in the international system? This is a central question that faces policymakers and one that has remained largely unexplored by scholars of international relations. This article argues that democratic peace theory speaks to the central factors that affect the risk preferences of states. Countries involved in Europe from 1816 to 1992 are analyzed to determine if levels of democracy and its constitutive elements affect risk-taking. Since critics argue that the strategic context affects the mechanisms underpinning explanations of the democratic peace, the effects of strategic variables on the relationships between regime type and risk-taking propensity are evaluated. Competing propositions are evaluated empirically using Bueno de Mesquita's indicator of risk with the EUGene dataset, which combines the Correlates of War and the Polity III data regarding regime type developed by Jaggers & Gurr. The results support the central hypothesis of the article - democracy is indeed associated with risk aversion regardless of the strategic context. However, the findings also suggest that states undergoing the transition to democracy from autocracy are more willing to take risks than are states with more stable forms of government. Further, the constitutive components of democracy have divergent effects on risk preferences.