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W. Benjamin’s Moscow Diary is a special kind of “physiognomy” depicting the revolutionary society of the 1920s as well as a text studded with “fragments” of Benjamin’s thoughts which were to configurate his “constellation.” Focusing on the concept of “toys” which Benjamin eagerly collected in Moscow, I attempt to outline its implication in the context of revolution. The problematics of “toys” are related to a key question in his philosophy of history: how should Revolution handle the “(legacy of its) past”? When Benjamin visited Moscow—the transition period (“waiting room of history”) from the age of experimental avant-garde to so-called Stalinism, most representatively social realism—scholars were divided on the issue of the “past.” If avant-garde aesthetics insisted on absolute rupture from the past, namely the “zero degree” of history, Stalinism asserted a privileged right to “use” the legacy of the past in utilitarian ways. The peculiar stance—twofold temporality—toward the past Benjamin’s concept of toys suggests is an example of using the past “differently” insofar as it neither abolishes the past nor limits itself in the concept of history as a linear time chain. Benjamin’s problematics of toys can offer new reflections on the well-known dilemma of Soviet revolution over the issue of “past.”