For a few years before and after 1900, Day rivaled Stieglitz as a promoter of Pictorialism, as turn-of-the-century artistic photography was called, with Boston rather than New York as its geographic center. Day was a largely self-taught photographer, connoisseur, and collector; a great admirer of Keats, Yeats, and Wilde; a publisher in the mold of British Arts and Crafts leader William Morris; and, like Stieglitz, an elected member of the Brotherhood of the Linked Ring, a Pictorialist breakaway from the Royal Photographic Society. In 1900 Day organized a massive exhibition, "The New School of American Photography," containing some 375 photographs by forty-two American Pictorialists. Sensing a threat to his international stature as the dominant photographic tastemaker, Stieglitz not only declined to participate but actively used his influence to block Day’s show from being presented at the rooms of the Linked Ring. Zaida Ben-Yusuf, who opened a fashionable portrait studio in New York in 1897, was among the photographers included in Day’s blockbuster show, which eventually took place at the Royal Photographic Society and, in 1901, at the Photo-Club de Paris. Unlike Day’s more formal portraits and figure studies, his portrait of Ben-Yusuf gives the impression of spontaneity and accident, with the subject off-center and backlit by a sunny window in the next room.
