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The collection consists of correspondence, writings, personal papers, and printed material documenting the career of Clarence Shepard Day. The collection provides insight into Day's work as an author, illustrator, and humorist, who often poked fun at upper class New Yorkers. The collection also documents Day's experience as an undergraduate student at Yale University in the late nineteenth-century. Correspondents include: Alfred A. Knopf and Vira Whitehouse.