While “passing” often refers to a person of color being accepted as white (the author of the story, Charles W. Chesnutt, was commonly thought to have light enough skin to “pass”), the passing in the story’s title is open to a different interpretation. Grandison passes for a content and loyal slave and continually seems to pass on freedom when allowed to flee. Grandison’s acts of “passing” ultimately allow him to free both himself and his entire family.

Finally, as with the character of Grandison himself, the whole story seems to “pass” as something it is not. Scholar Martha Cutter notes that, throughout the story, Grandison “passes” for a loyal slave, confirming Dick and Colonel Owens’s ideas of what a content slave should say and do (Cutter, Martha J. “An Intricate Act of Passing: Strategies of Racial and Textual Subversion in Charles Chesnutťs “The Passing of Grandison’” CEA Critic, vol. 70, no. 2, 2008, pp. 46). Dick’s initial pick to accompany him North is his attendant Tom, who is Grandison’s cousin. When Dick asks Tom to go North, Tom immediately realizes the opportunity for freedom, which he had thought about often but never put into concrete plans. Tom realizes that he cannot let Dick know about his intentions and that he must “dissemble his feelings” (61).