Set in the 1850s and first published in 1899, Charles W. Chesnutt’s "The Passing of Grandison" is a short story about a Southern slave owner's son's attempt to free a slave whose stubborn loyalty foils his plans.
In an era when it is a federal crime to help slaves escape to free states or Canada, Dick Owens, the lazy son of a Kentucky plantation owner, hopes to impress the woman he is courting with a scheme to bring one of his father's slaves on a trip to the free states in the North. When Colonel Owens worries his son's personal attendant will be swayed by "rascally" abolitionists, the slaveholder recommends his son take Grandison, his most-loyal slave. In New York and Boston, Dick presents Grandison with several opportunities to leave his service and become a free man, but Grandison remains immune to the arguments of the abolitionists who try to convince him to escape. On the Canadian side of Niagara Falls, Dick hires several men to kidnap Grandison as a means of freeing him. Three weeks after Dick returns to Kentucky, Grandison arrives in a worn-out state and tells a tale of deprivation in the Canadian wilderness. Dick's father is overjoyed to have Grandison back, but Grandison soon escapes, bringing his family with him this time. The disillusioned colonel tracks the fugitive slaves' progress North, but the Underground Railroad network of refuges whisks Grandison's group to Canada before the colonel can catch up. The colonel last sees his formerly loyal slave on a boat heading across Lake Erie to freedom.
Published in 1899 as part of his collection The Wife of His Youth and Other Stories of the Color-Line, "The Passing of Grandison" is Chesnutt's comedic look back on an era before slavery was abolished. Through the use of multiple points of view and many ironic twists, the pioneering African-American author explores themes of loyalty, duplicity, abolitionism, and freedom. With the enigmatic figure of Grandison, Chesnutt paints a portrait of a slave who exploits his owner's self-aggrandizing belief that slaves prefer the security of life on the plantation to the uncertainty of being free.