Abstract
Portals: Windows, doors, black holes, white holes and worm holes serve as nodes for transport between different systems of organization in the works and writings of Marcel Duchamp, and in Thomas Pynchon's novels _Gravity's Rainbow_ and _Vineland_. These portals enable pivoting between different forms of cognition, in the realm of the social and political with respect to subject positions with reference to chess, and in the realm of the individual with respect to subject formation and human creativity. Drawing on the philosophy of Gilles Deleuze and Felix Guattari, and on the cognitive science of Francisco Varela and Edwin Hutchins, a connection is made between an avant-garde modernist, and a post-modern novelist, in their attention to a war between top-down (control) and bottom-up (emergent) processes in society and self. This investigation becomes a way to rethink the terms modernism and postmodernism.