As pointed out by a number of scholars, Henry James frequently uses monetary images to describe his characters and their relationships to society throughout his fictional works. In The Wings of the Dove, Milly Theale, one of James’s major phase protagonists, tends to be treated according to her financial background and tragic situation by her worshippers and those who envy her wealth. However, Milly’s great fortune does not necessarily imply vulgarity but rather a strength that shows the supreme spirituality of her presence. The treatment of the power of wealth is more elaborately depicted in multiple ways as compared to James’s early phase fictions such as Daisy Miller and The Portrait of a Lady. James also seems sympathize with Merton Densher, an English journalist in The Wings of the Dove, because of his indifference to moneymaking and an appetite for success despite his lack of masculinity and passivity. Through the characterization of Densher, one can see that James in his later works seeks fresh possibilities and solutions for the conflict between two different concepts that James finds in a class-oriented English society and financially developed America in the early twentieth century.