“The Passing of Grandison” demystifies the stereotypical image of a slave in the 19th century. Author Charles Chesnutt uses his personal experience and ability to impersonate a white man to tell a very compelling story. Grandison was more than an uneducated farmhand carrying out his master's orders. “The Passing of Grandison” proves that although society at the time viewed slaves as nothing more than property to be purchased and abused, slaves could be much more than what existed on the surface. In Chesnutt's "The Passing of Grandison," Grandison is a plantation slave in the early 19th century who, through his actions, eventually escapes and gains his own freedom and that of several members of his family. Most people have found themselves in a situation where they wish they could outwit or outwit others. Whether a peer or a superior, many people wish they had the ability or courage to gain the upper hand over others. Is it possible for a subordinate to really deceive his superior and ultimately get what he really wanted? This is accomplished through the actions of a trickster character. A trickster is a literary character who attempts to outwit and outwit his adversaries. The trickster uses any means necessary to achieve his desired goals. As Trudier Harris says, “crooks achieve their goals through deception and the wearing of masks, playing on the credulity of their opponents” (Harris, 1). In "The Passing of Grandison", Chesnutt uses a trickster character to carry out this one-up-man and twists while providing social commentary to present part of his own belief system regarding the treatment of slaves in the 19th century. Two characters in “The Death of Grandis...... middle of paper ......The Death of Grandison. Boston: Houghton Mifflin, 1899. Delmar, Jay. “The Mask as Them and Structure: The Sheriff's Children and the Death of Grandison by Charles W. Chesnutt.” American Literature (1979): 364-375. Dunbar, Paul Lawrence. Norton Anthology of American Literature. United States: WW Norton and Company, 2003. Harris, Trudier. “The Trickster of African-American Literature.” Server of the professor of history of freedom (nd). 05 03 2014. <>.Mitchell, Margaret. Gone with the wing. New York: The Macmillan Company, 1936. Montgomery, Georgene Bess. “Tests and Tips: Elegba in The Goophererd Grapevine and the Passing of Grandison by Charles Chesnutt.” Studies in Literary Imagination (2010): 5-14.Schlosser, SE Brer Rabbit and the Tar Baby. Guilford: Globe Pequot Press, 2012.