Any study of Willem de Kooning is inevitably speculative. As an artist he was more concerned that the viewer "never know" and in provoking questions rather than presenting answers. The diverse and disjointed de Kooning literature bears witness to his success in this regard and to the opaque nature of his achievement. Recognizing the obdurate character of de Kooning's work, this essay, rather then directly pursuing meaning, has instead tried to address the question of how de Kooning's interest in eluding definition manifested itself in one of his most important collage paintings, Asheville of 1948. The first part of the thesis reconstructs the collage painting process of Asheville presenting it as a descriptive enterprise in which de Kooning consciously pursued the more chaotic "unknowable" aspects of his visual life by illusionistically recording fragments of objects and momentary glimpses of events. Recognizing de Kooning's interest in depicting fragmented phenomena as the underlying source for the visual chaos of Asheville illuminates the painting's relationship to long established traditions of description and illusion in Western art exemplified by the letter rack paintings of 19th century American art and 17th century Dutch art. Finally, as the contentious debate over meaning in Dutch painting illustrate, descriptive works of art, because of the ambivalent way they engage disordered aspects of visual experience, are particularly difficult to interpret. In his conscious allegiance to older descriptive and illusionistic traditions in Asheville de Kooning had found an especially effective way to obscure meaning.