This article presents the career of the Russian poet-translator Mark Tarlovskii (1902–1952) through the prism of the trickster archetype as applied to Soviet culture by Mark Lipovetsky (2011). Drawing on both published and archival material, the article traces Tarlovskii’s navigations through “cynical culture” in the Soviet 1930s and 1940s. While these were arguably survival strategies on the part of the translator, they had as yet unrecognized implications for the field of literary translation and Soviet “nationalities culture” at the time. Furthermore, these navigations help to unearth a “southern subjectivity” whose significance for Russian culture of the epoch is still understudied.