Paul Auster’s The New York Trilogy has been hailed as a postmodern novel that comprises the world of uncertainty inhabited by fragmented subjects, and has also been acclaimed as one of the canonical postmodern fictions. Recent criticisms, however, tend to rethink the equation between Auster’s novel and postmodernism, suggesting that, for example, the subjectivity represented in City of Glass seems less like the decentered postmodern subjectivity than a figure based on the desire to reconstitute the modern self. This paper attempts to reassess Auster’s novel in view of its reconfiguration of the dialectics of modernity and postmodernity, focusing on its topographical representations of New York City as utopias and heterotopias. In City of Glass, Daniel Quinn’s de Certeaurian urban practices of lacking a place construct his textual subjectivity by producing counterspaces of heterotopias against Stillman’s project of appropriating Manhattan as a (pre)modern utopia. The (dialectical) outcome of Quinn’s postmodern spatial practices that work as a counter-commentary against Stillman’s search for totalizing visions of a utopia in a unitary, thus implicitly negative, way turns out to be not synthesis, but only loss. Ghosts, the second part of the novel, is also preoccupied with the dialectic relationship between modernity and postmodernity, the interrelationship among subjectivity, space, and textuality, and the uncanniness of doubling subjects mirroring each other. In the conclusion, this paper reconsiders the possibility of Jamesonian “cognitive mapping” as an inevitable way of trying to recognize the impossible totality as possible in this era of the impossibility of representation.