This article considers Walter Benjamin’s portrait of the gambler in light of his critique of bourgeois culture and view of modernity. Benjamin’s gambler reveals a distinctive relationship to time, political and economic history, and the pathos of a class society. To illustrate these features of Benjamin’s allegorical image of chance, the article considers it alongside an alternate image found in Benjamin Constant’s portrayal of Napoleonic warfare. Finally, and in connection with the gambler, the article draws out the aleatory elements of yet another of Benjamin’s dialectical images: the destructive character. In these various figures, Benjamin’s political thought—and his approach to political thinking through dialectical images—comes into sharper relief.