• This paper explores the life of Joseph Grigulevich (1913–1988), a famous early Soviet illegal intelligence operative, who conducted various “special tasks” on behalf of Stalin’s foreign espionage network. These included the murder of dissident Spanish communist Andreas Nin (1938), a participation in the assassination of Leon Trotsky (1940), posing as a Costa Rican ambassador (1949–1952), and an abortive project to assassinate Joseph Bros Tito (1952). In contrast to conventional espionage studies that are usually informed by diplomatic, political, and military history approaches, I employ a cultural history angle. First, the paper examines the formation of Grigulevich’s communist and espionage identity against his background as a cosmopolitan Jewish “other” from the interwar Polish-Lithuanian realm. Second, it explores his role in the production and invention of intelligence knowledge, which he later used to jump start his second career as a prominent Soviet humanities scholar and a bestselling writer of revolutionary non-fiction.