In her 2010 article “Aesthetic Wit(h)nessing in the Era of Trauma”, Griselda Pollock lamented the aperture between psychology, particularly that of PTSD, and esthetics in the search to bear witness to traumatic experience. This article explores the gray area that exists when the esthetic and the traumatic converge, arguing that such areas exist not only as direct representations of the difficulty of narrativizing trauma as described by such theorists as Cathy Caruth, Onno van der Hart, and Bessel van der Kolk, but also simultaneously as windows into the moments of what Dominick LaCapra calls “the sublime object of endless melancholia and impossible mourning”. Postmodernism is argued to be the organic choice of voicing traumatic retellings, and close readings of John Hersey’s proto-postmodern Hiroshima (1946), Tim O’Brien’s The Things They Carried (1992), and David Foster Wallace’s Infinite Jest (1996) work to highlight the intersections of trauma, postmodern literature, and esthetics; or, in Wallace’s case, theoretical discussions of traumatic tropes as facilitated by the postmodern tradition. In drawing attention to this tripartite convergence, this article hopes to continue in the vein of scholarship that reaffirms the need for evermore research in the field of trauma studies as well as substantiate a claim of the heightened importance of postmodern literature in the 21st century—an epoch indelibly marked by trauma, as noted by Pollock.