This essay begins with a personal insight into the achievements of my grandfather, Rao Sahib K Kothandapani Pillai. Born in 1896 at Andalur Semmangudi village in South India, Kothandapani Pillai is celebrated as the earliest Tamil writer to take the initiative of translating Tolstoy’s works into Tamil. A diplomat who read Tolstoy for pleasure, Kothandapani Pillai translated three stories––Two Old Men’ (‘Dva starika’, 1885), ‘How Much Land Does A Man Need?’ (‘Mnogo li cheloveku zemli nuzhno?’, 1886), and ‘A Lost Opportunity’ (‘Upustish’ ogon’––ne potushish’, 1885)––published in 1932 in Kadhaimanikkovai (Stories from Tolstoy), an academic textbook for primary-school children. The second part of this essay examines my grandfather’s translator-successors who, between 1930-1970, continued to produce Tamil translations of Tolstoy and other authors such as Maksim Gorky, Fedor Dostoevsky and Anton Chekhov, for Progress and Raduga publishers in Moscow.