He worked in the decoration department of the Chicago Exposition, and after moving to New York City in 1897, he was the art critic of Harper's Weekly, the New York Evening Post, the New York Sun (1901–04), the International Studio, and the New York American.
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Stieglitz enlisted Caffin as a writer for his journal Camera Work, for which he wrote appreciations of Stieglitz's photographs as well as those of Edward Steichen, Frank Eugene, Joseph Keiley, Gertrude Kasebier, among others.
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