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This paper discusses the writings of two Trotskyist theorists from the “civil war generation” in the Bolshevik Party: Polina Vinogradskaia and Grigory Yakovin. Their writings on the German workers movement, and its traditions of statism and reformism, provide insight into the Trotskyist critique of the politics and theoretical origins of Stalinism. Both were trained at the Institute of Red Professors in the 1920s to become part of the new party and state elite; they were imprisoned by the late 1920s. However, their paths diverged by 1930: like her husband Evgeny Preobrazhensky, Vinogradskaia left the Opposition and even managed to survive the terror. Yakovin, by contrast, remained one of the theoretical leaders of the Opposition in the prisons and camps and was executed in Vorkuta in 1938. Yakovin’s writings remained unavailable in the Soviet Union for decades, whereas Vinogradskaia was able to publish again in the post-war period. These case studies testify to both the intellectual influence of the Opposition in the 1920s, and the impact of the terror, in which all active Trotskyists were systematically murdered. At the same time, the case of Vinogradskaia shows that the Opposition and its representatives, though destroyed organizationally and politically, were never entirely removed from Soviet intellectual life and its key academic institutions.