Taking canonical literary texts as sources for drawing or poetry-writing, the New York Sketch Club’s meetings seemed to epitomize the notion that its members—writers and artists including William Cullen Bryant, Thomas Cole, and Asher Durand—were “kindred spirits” engaged in a shared project of consolidating national identity through aesthetic practice. This essay, by contrast, describes the club’s obsession with optically and textual uncertainty—including illegible handwriting, sketches based on radically reimagined literary sources, and weakly visualizable artworks—as shaping a literally less-visible register of involvement with the violence of tribal dispossession and African slavery. Racialized forms of power appear in this account as forces underwriting the canon of “American” art that developed through the pictorial and narrative activities of the Sketch Club.