Loyalty
As a story about an enslaved man who refuses to choose freedom, "The Passing of Grandison" depicts—or at least would seem to depict—Grandison's extreme loyalty to his white owners. The theme first arises when Dick and his father discuss Dick's trip North. Believing that Tom, a younger slave, may be swayed by those who tempt him to escape, Colonel Owens recommends that Dick take Grandison, an older slave who says all the right things to make the colonel believe he is "abolitionist-proof." Grandison gives this impression by parroting his master's lines about the misfortune of freemen who have no one to take care of them or provide the relative luxuries of the plantation. Colonel Owens is so taken in by Grandison’s ability to tell him what he wants to hear that he believes Grandison actually prefers slavery to freedom. When Grandison refuses to leave Dick's service during the trip, and acts frightened at the possibility of being abducted, it seems to Dick that Grandison's stubborn loyalty will thwart his plan. At the end of the story, Grandison returns to the plantation only so he can sneak his family out and bring them with him to Canada. With this action, Chesnutt shows that Grandison is a sincerely loyal man. His loyalty is to his family, however, and not the white slave masters.
Duplicity
Alongside loyalty is the complementary theme of duplicity. The theme first arises when Dick develops his plan to release one of his father's slaves while in the North. To achieve his goal, Dick lies to his father, claiming to wish to travel so that he may restore his health. This duplicity creates dramatic tension, because the reader knows Dick's true intentions. Chesnutt's dramatic irony also injects humor into the story, as Grandison is oblivious to how much consternation he is causing Dick by remaining loyal. Having run out of options, Dick deceives Grandison while in Canada by hiring men to kidnap him. The most significant act of duplicity comes at the end of the story when Grandison flees the plantation with his family. It is at this point that Colonel Owens understands his 'most-loyal' slave had been deceiving him all along. Rather than sincerely believing that life on the plantation was preferable to freedom, Grandison had been lying to the slave master as a survival strategy.
Abolitionism
Another of the story's most significant themes is abolitionism—the belief that the institution of slavery should end. Set in the 1850s, "The Passing of Grandison" takes place at a time when anti-slavery sentiment was popular in the United States, and the Underground Railroad was helping tens of thousands of enslaved Black Americans to flee the South. The theme enters the story when Charity Lomax says her Quaker heritage is activated inside her whenever she hears of a master treating a slave cruelly. As the first organized religion in the U.S. to condemn slavery and forbid its members from owning slaves, the Quakers were active in the abolitionist movement. A less-favorable view of abolitionism arises when the colonel rants to his son about the "rascally" abolitionists who have been filling people's heads with ideology and interfering in what he considers a mutually beneficial relationship between master and slave. In response to growing resistance to slavery, slaveholders like Owens petitioned judges and politicians to impose harsh penalties on those caught helping slaves escape. Abolitionism eventually wins out over the slaveholders, but not until after the American Civil War.
Freedom
Freedom is among the most important themes in "The Passing of Grandison." Chesnutt establishes the theme in the narrative commentary on the trial of the young Ohio man who is severely punished for trying to help a slave attain freedom in the North. Chesnutt builds on the theme with Dick's scheme to release one of his father's slaves in Canada. His personal attendant, Tom, is eager for freedom, but the colonel correctly guesses there is too much risk in letting Tom go. Grandison, however, says things that make the colonel believe he prefers life on the plantation to the alternative of freedom. Grandison continues to act as though freedom is a frightening prospect while traveling with Dick. However, it becomes clear at the end of the story that Grandison values freedom as much as anyone else; he simply knows his individual freedom means nothing if his family is still in bondage.
