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This study analyzes theoretically and empirically the background of the rise to power of Vladimir Putin in Russia and Recip Tayyip Erdogan in Turkey. It situates this analysis in the contexts of the historical assessment of the fragility of liberal democracy and the persistence and growth of authoritarianism, populism, and dictatorship in many parts of the world. The authors argue that the question whether Putin and Erdogan can make Russia and Turkey great again is hard to confirm; personal ambition for power and wealth is certainly key to an understanding of both rulers. They each squandered opportunities to build from free and fair democratic electoral legitimacy and economic progress. The prospect for restored national greatness depends on how they can handle the economic and political challenges they now face and will continue to face in the near future, in a climate of global pandemic and economic recession. Both rulers so far have succeeded in maintaining and increasing their powers and influence in their respective regions, but neither has made real contributions to regional stability and order. Chaos seems to be growing, and the EU and the U.S. thus far seem unable to provide coherent responses to mitigate the impact of their adventurism and disruption.