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Will Russia’s war tip the Kremlin even further toward tyranny while fortifying Ukraine's democracy? That will depend on Vladimir Putin and Volodymyr Zelensky as much as on the course of the war itself. If, from a democratization perspective, Ukraine prior to the war had been a work in progress, Russia was the inverse: a work in regress. It is an open question whether a debacle in Ukraine would tip Russia toward tyranny, toward a more modern and representative regime, or toward chaos.