Explain how "The Passing of Grandison" plays with the idea of passing. Talk about how Chesnutt is using the term passing in a different, even more complex way than its general usage in this brilliant story. Typically, passing would refer to people of color with a lighter skin tone passing as white. How is passing different in this short story? Who is pretending to be something they are not, and why?

"The Passing of Grandison" plays with the idea of passing through the title character's apparent acquiescence to the demands of enslavement. By pretending to be loyal to the slaveholders, Grandison eventually achieves freedom, not only for himself but also for his family. Their passing included physically moving out of the South and the United States and, conceptually, out of bondage.

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In his story "The Passing of Grandison," Charles Waddell Chesnutt explores the attitudes and actions of Grandison, an enslaved African American man living in pre-Emancipation Kentucky. During much of the story, Grandison is portrayed as passive and accepting of the institution of slavery. His behavior engenders such a high level of trust in the plantation owner, Colonel Owens, that Owens trusts Grandison more than his son, the irresponsible young master Dick. The white characters also believe that Grandison and all African Americans are of limited intelligence. It does not occur to them that he would be concocting a clever scheme that would play out over a long period of time.

Grandison, however, is very well positioned to observe and understand the nuances of the white people's attitudes and behavior. He fully exploits their underestimation of his intelligence and skills—one of which is exercising tremendous patience. Not only does Grandison accompany Dick on his Northward journey, he repeatedly thwarts the young man's efforts to free him. Grandison is far more capable than Dick is to understand the motivations and implications of his actions. While Dick thinks he is using Grandison, the reverse is true: Grandison uses him as a guide to the escape route he will later retrace. Furthermore, his greatest concern is for his family, not himself—and certainly not the Owenses. Through long-term planning and assuming a façade of loyalty, Grandison ultimately succeeds in liberating his family.

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