Montage as an aesthetics of fragmentation, initiated by modern paintings of reflecting the modern disintegration of organic community, has been explored by a wide variety of art, including literature and cinematography. Especially by Russian film-makers such as S. Eisenstein, V. Pudovkin, and D. Vertov, the aesthetics of montage has been evolved into the montage of “linkage” and “collision,” then reaching its maturity in the montage of dialectics, although it was the American D. W. Griffith who initiated “the parallel montage” and then inspired the Russians. Literary writers, both European and American, also embodied the aesthetics of montage into their fictions, as was clearly shown in the novels of John Dos Passos. As “contemporary chronicles,” the narrative structures of Dos Passos``s major novels from Three Soldiers and Manhatttan Transfer to the U.S.A. trilogy creatively hire the aesthetics of montage in order to portray the modern historical landscapes of American capitalism during the early decades of the 20th century. By the architectural use of montage, the critically-acclaimed novels have successfully achieved their literary goal of delivering the historical consciousness of dialectical radicalism in order to expose the inhumane contradictions of modern American capitalism. Therefore, the main purpose of this essay is to clarify how much the montage itself, not only as an aesthetic technique but also as a way of thinking, contributes to their historical consciousness. Most of critical discourses about the aesthetics of montage seem to have been limited to the analyses of its formal and technical aspects. However, this essay proposes that the aesthetics of montage has in itself historicity, therefore prefiguring a certain historical consciousness of cairology, which defies the modern concept of chronological time. W. Benjamin’s montage as “dialectical image” brings up the constellation between the past and the present, inspiring the utopian solutions of history, while the montage of G. Deleuze as the image of time, not the image of movement, induces the interaction between the past and the present in accordance of “the whole.” The novels of Dos Passos also employ, in their narrative structures, the dialectical montages to portray the modern history of American capitalism with the image of time, consequently inspiring the utopian moment of the dialectical totality of history.