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The purpose of this paper is to investigate the self-contradiction in Alexander Pope’s attempt to fashion himself as a gentleman born of the literary market. For this purpose, this paper examines the cause of Pope’s desire to detach himself from the emerging eighteenth-century literary market that brought him huge commercial success and thus his independence from patrons, publishers and even politicians. Through the analysis of “An Epistle to Dr. Arbuthnot,” it examines how Pope fashions himself as a new ‘manly’ elitist distinguished from the mob of the literary market and corrupt traditional aristocracy. Pope creates himself, it is argued, as the champion of traditional masculine elite culture as opposed to the emerging feminized commercial culture. In the reading of the 1743 Dunciad, it analyzes how Pope criticizes and feminizes the literary mob of the Grub Street; how Pope deplores the diffusion of commercial and feminized culture in the presentation of the final triumph of the goddess Dulness; how, in so doing, Pope manages to fashion himself as a lone gentleman born of the market in a nation subsumed by vulgar and thus corrupting literary culture. Finally, this paper identifies the innate contradiction in Pope’s fashioning of himself as a gentleman through the analysis of contemporary counter-attacks on him that expose the commercial motive of his attacks on Grub Street, condemn his femininity, and celebrate the commercial literary market as a new mode of literary production.