Literature played an important role after the Second World War in effecting the ideological transformation of citizens of the communist countries of Eastern Europe into the so-called Homo Sovieticus. The Adventures of Cipollino, an allegory of class struggle and revolution by the Italian communist writer Rodari, was translated in the early fifties – at the height of the Cold War – into the different languages of the Soviet Republics and quickly became one of the most popular children’s books in the USSR. This chapter compares the Russian translation of Cipollino published in 1953 with the Estonian translation published in 1960 to investigate the complexity of the Soviet polysystem and its diachronic evolution, including the tense relations between the centre (Russia) and the periphery (Estonia) of the Soviet Empire and changes in Soviet politics after Khrushchev’s 1956 denunciation of Stalinist crimes. Following Hermans, the aim is to develop a discourse on translation as “a cultural practice interacting with other practices in a historical continuum” in order to reveal its “formative role in history”.