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Grigory Vinsky (1752-1818) was a nobleman from Ukraine whose checkered career took him to the Kyiv Mohyla Academy, the Izmailovsky Guards Regiment, a dungeon in the Peter-Paul Fortress, and finally exile in Bashkiria. Looking back on his life in his autobiography My Time, Vinsky develops a complex set of arguments about education, the judiciary, prisons, politics, and the state of public morals in the Russian Empire. This paper will explore Vinsky’s conception of despotism and enlightenment as central realities in Russian life under Catherine II.