“The Passing of Grandison” by Charles Chesnutt dispels the stereotypical image of the slave in the 19th century. Author Charles Chesnutt uses his personal background and ability to pass himself off as a white man to tell a very compelling story. Grandison was more than an ignorant farm laborer who did his master's bidding. “The Passing of Grandison” provides evidence that while society at the time thought of slaves as nothing more than property to be purchased and abused, slaves could be much more than what was on the surface. In Chesnutt's "The Passing of Grandison" Grandison is an early 19th century plantation slave who through his actions ultimately manages to escape and gain his own freedom as well as that of several family members. Most people have been in a situation where they wish they could outwit or outsmart another. Whether it's a peer or a superior person, many wish they had the ability or courage to get the better of others. Is it possible for a subordinate to actually deceive his superior and ultimately get what he really wanted? This is achieved through the actions of a trickster figure. A trickster is a character in literature who attempts to outsmart and outmaneuver his opponents. The cheater uses any means necessary to achieve whatever goal he desires. , says Trudier Harris, “cheaters achieve their goals indirectly and by wearing masks, playing on the gullibility of their opponents” (Harris, 1). In “The Passing of Grandison,” Chesnutt uses a trickster figure to get that unique vessel and plot twists, providing social commentary to present part of his belief system as it relates to the treatment of slaves in the 19th century. Two characters in “The Disappearance of Grandis…… in the center of the sheet……The Disappearance of Grandison. Boston: Houghton Mifflin, 1899.Delmar, Jay. “The Mask Like Them and the Structure: The Sheriff's Sons and the Disappearance of Grandison by Charles W. Chesnutt.” American Literature (1979): 364-375. Dunbar, Paul Lawrence. Norton Anthology of American Literature. USA: WW Norton and Company, 2003.Harris, Trudier. "The Trickster in African American Literature." The service of the teacher of the history of freedom (n.d.). 05 03 2014. <>.Mitchell, Margaret. Off with the Wing. New York: The Macmillan Company, 1936. Montgomery, Georgene Bess. “Testing and Deception: Elegba in Charles Chesnutt’s The Goophererd Grapevine and the Passing of Grandison.” Studies in the Literary Imagination (2010): 5-14.Schlosser, S. E. Brer Rabbit and the Tar Baby. Guilford: Globe Pequot Press, 2012.