This article examines Lev Tolstoy’s translations of Laozi’s Dao De Jing, the ancient Chinese Daoist canon, from English, French, and German into Russian, and depicted a canonical Russian writer’s participation in an evolving global intellectual network of translating Chinese classics for the first time in full. I argue that Tolstoy constructed Laozi as a cosmopolitan philosophical ancestor for Russia and Europe and an ideological ally in the polemical rethinking of Christianity and the future of Western civilization. I begin with Tolstoy’s first encounter with the Dao De Jing during his spiritual crisis in the 1870s and 1880s and his invocation of Laozi to intervene in the debate on modernization between Emile Zola and Alexandre Dumas. I then explain Tolstoy’s understanding of the kinship of Dao, Logos, and God against the background of his polemics with the Russian Orthodox Church. I conclude by examining how Tolstoy used the Dao De Jing to exhort coeval Chinese intellectual Gu Hongming to accept the nonviolent resistance to imperialism. Tolstoy’s struggle with translating the Dao De Jing exemplifies an intellectual dilemma: in the attempt to show that Christian doctrine held no monopoly for universal truth, Tolstoy obliterated the specificity of Laozi’s cultural context.