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This paper examines the intellectual trajectory and evolving social circles of the Soviet literary critic Leonid Pinsky, a scholar of Renaissance literature. Drawing on archival documents and memoirs from Pinsky’s contemporaries, this paper begins by charting Pinsky's rise to recognition as a lecturer at Moscow's Institute of Philosophy, Literature, and History (IFLI) during the 1930s. It also examines his collaboration and friendship with Mikhail Lifshitz, a notable Marxist theorist and a leading figure in the intellectual movement known as the 'Current'. Following his arrest in 1951 during the anti-cosmopolitan campaign and subsequent five-year detention in the Gulag, Pinsky emerged as an influential figure within Moscow's dissident circles during the 1960s and 1970s. The paper also explores Pinsky's eventual estrangement from Lifshitz, driven by their diverging views on Stalinism and the Soviet intervention in Hungary in 1956 (this split was extremely painful for Pinsky, who considered Lifshitz his teacher despite the two of them being of the same age). Ultimately, this paper, through the case of Pinsky and his immediate circle—including his enduring friendships with former IFLI students and his involvement in the dissident movement—examines the transformation of the structure of intellectual circles in Moscow during and after Stalinism.