This essay argues that the key to Benjamin’s political thought lies in his appreciation of aesthetic production. Avoiding both uncritical celebration and fatalistic condemnation of the role played by modern technologies within production, Benjamin articulates a nuanced interpretation of the political potential of aesthetic modernism. More than a mere theoretical appreciation of the avant-garde, Benjamin’s work represents a sustained attempt to apply modernist methods of production to the practice of theory itself. Benjamin’s experiments carry the expectation that the reception of theory will be similarly transformed, thereby pointing the way to a radically new manner of pedagogical communication. By way of conclusion, Benjamin’s line of thinking is applied to recent debates on the use of online learning within the contemporary academy.