William Carlos Williams discovers significant sources of inspiration in the revolutionary avant-garde movements, in particular, Dada and Surrealism. He tries to pursue the experimentalist innovations in them for his own poetic needs. Williams’s desire to establish an indigenous American poetic work is compatible with his avant-gardist experimentation with objets trouves. Williams puts forth his greatest effort into dedicating himself to hearing the voices and understanding the lives of marginalized people he comes across, and he translates his observations with poetic language freed from their instrumental contexts. His early poetry written from the 1910s to 1930s betrays American social ruination, and his goal to give voice to the conflictual and fragmentary character of modernity is carried out by the Surrealist formulation of montage. In that formulation, the dialectical image not merely becomes a central trope for deciphering the myth of modernity, but it functions as both subject and object in the historiographic narratives of Walter Benjamin and Williams. Objets trouves and dialectical images become the most pivotal tropes that do justice to the diverse facets of social reality Williams attempts to disclose throughout his career as a modernist poet.