Rather than establishing literary relations with Russian intellectuals or securing the affections of his Latvian love interest, Walter Benjamin spends most of his 1926–27 Soviet sojourn shopping for toys. Benjamin’s habits present an interesting counterpoint to his communist surroundings; he is collecting while Russians are collectivizing. Through the lens of his toys, this article examines the conflicted practice of collecting, locating a tension between Benjamin’s theory of historical materialism and his appreciation for objects as artistic, auratic, and transformative. Drawing on contemporary criticism of ethnography, it proposes that precisely in its inability to reconstruct the context of its objects, Benjamin’s Russian toy collection becomes a site of artistic transformation rather than a forum of historical preservation. The article reads his toy collection as a critical autobiographical moment that stages the complex childish, antiquarian, and playful dimensions of collecting more clearly than Benjamin’s later scholarly reflections.