On its surface, Herman Melville’s short story, “Bartleby, the Scrivener: A Story of Wall Street” (hereafter “Bartleby”) seems to portray a benevolent employer who faithfully puts into practice the spirit of charity, as specified in John Winthrop’s “A Model of Christian Charity.” According to Winthrop, the ideal society of a “city upon a hill” can be established on the basis of the gap between the rich and the poor. He predicts that love or brotherly affection between the two would encourage the rich to exercise charity to the poor while leading the latter gratefully to obey the former in return, thereby accomplishing the vision of a city upon a hill. Following this vision of an ideal society, the lawyer-narrator of “Bartleby” serves to intensify the hierarchical division between the rich and the poor in 19th-century New York City by facilitating the increase of the former’s wealth through his legal documents and by impoverishing the latter through exploitation and foreclosures. In this sense, the capitalist world on Wall Street precisely embodies the economic structure needed to build a “city upon a hill.”As evidenced by Bartleby’s death, however, this city upon a hill disintegrates: mercy, the supposed principle of integration, has degenerated into a principle of disintegration in the reality of the severe market competition of 19th-century American capitalism. To be more specific, mercy, a concept premised on economic stratification, has rationalized the fatal attempts of the rich to drive the poor such as Bartleby to death for their profit. Furthermore, the rich have even been induced not only to ignore and shun but also eventually to remove anybody who voices a refusal to be exploited or demands social reform to improve the working conditions because such individuals undermine the economic foundation of mercy: the gap between the rich and the poor. As a result of this contradiction inherent in the principle of mercy and a “city upon a hill,” Bartleby commits suicide, undeniably abetted by the lawyer. The contradiction also obliterates the latter’s humanity and emotions such as pity and love. Nothing remains for the lawyer except the impersonal system of capitalism, which can desert him at any moment as he himself did to Bartleby. Inherent in the vision of Winthrop’s ideal society, this structural limitation still dominates modern capitalism. The lawyer’s—or our own—hypocrisy as a benevolent employer continues to lead us to overlook or even to exacerbate the frustration of yet another Bartleby. The author, Melville, therefore asks us to confront the “dead wall,” the structural limitation embedded in our city upon a hill, together with Bartleby and him even though it casts a large gloom over us, reminding us of our tenacious failure to overcome it.