Initially among the Bolshevik Revolution's most ardent supporters in the United States, anarchists rapidly became its most outspoken left-wing critics. This article focuses on the transnational exchanges of information, analyses, and individuals that caused this about-face and its repercussions. Hundreds of Russian-born anarchists returned from the United States in 1917 and participated in the revolutionary upheavals in Russia, only to subsequently face repression and disillusionment. Their experiences in turn provided the basis for their American comrades' understanding of Soviet Communism as a betrayal of the popular revolution originating “from below” and an inherently authoritarian system. Anarchists' new anti-Communist imperative decisively shaped their activities in 1920s and 1930s, while simultaneously leading to their increasing marginalization within the labor movement and the Left. Conflict between anarchists and Communists erupted within the Industrial Workers of the World and the International Ladies' Garment Workers' Union, to the detriment of all. It also spilled over into the anti-Fascist movement and, subsequently, into anarchist understandings of, and participation in, the Spanish Civil War. The Bolshevik consolidation of power, the advent of the Popular Front, and the fall of Spain simultaneously provided anarchists with important insights into the nature of Soviet Communism, cemented their antiauthoritarian beliefs, and rendered them ineffective by placing them outside of the emerging Cold War dichotomy of the Stalinist “Left” and anti-Stalinist “Right.”

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