Dick Owens, the wealthy young protagonist of Charles Chesnutt’s “The Passing of Grandison,” is the pampered only son and heir to a plantation and all its enslaved workers. Indolent and entitled, Dick seems never to have faced serious opposition to whatever he wants—until the woman he loves dismisses him as unserious and the one man who can help prove her wrong acts in a mysteriously stubborn way. As he deals with frustration and obstruction, Dick perseveres, learning to see past superficial appearances and understand others’ motivations more fully.

Born into privilege and wealth, Dick is also “intelligent, handsome, and amiable.” He has everything going for him but doesn’t care to do anything with his advantages. He lacks, the judge who tries to teach Dick law says, “the whip of necessity” and “the spur of ambition,” at least until the woman he loves, Charity Lomax, finds a way to simulate whip and spur. The story’s inciting incident happens when Dick discovers that Charity romanticizes a “heroic” man who aided a fugitive slave fleeing north. He failed, was imprisoned, and died—but he tried. Charity can’t love a man until he has “done something,” and Dick, she claims, never will. Dicks begs his sweetheart to put him to the test and decides to emulate the Ohioan, but to more successful ends.

He wastes no time as the story’s rising action begins. Easily obtaining his indulgent father’s permission to travel north for several weeks, Dick takes with him Grandison, an “abolitionist-proof” slave whom Colonel Owens trusts and has given permission to marry Betty, a maid Grandison is “sweet on.” They travel first to New York, where a series of standoffs begins between the placid Grandison and the increasingly irritated young man who assumes that any slave would gladly take the chance to flee north. It’s almost as if they are playing a game of chess: when Dick makes a move that opens the way for Grandison to win, Grandison’s countermove resets the board in Dick’s favor. Dick sees Grandison as an affable and perplexingly loyal servant, and because he can’t get past his own biased perspective about the slaves who work on the plantation, he doesn’t think hard enough about why Grandison keeps passing up opportunities to win the game of freedom. While keeping Charity’s “clear blue eyes” in mind, Dick completely forgets that Grandison may be thinking, from time to time, of Betty.

In New York, Dick chooses a hotel where free Black men work. He makes sure Grandison has pocket money. To slip away would be easy. Yet Grandison not only stays but claims to think himself better off than the free men. Stymied, Dick moves on, with Grandison in tow, to Boston, which at the time was a hub of abolitionist activity. There, he throws Grandison into the path of abolitionists. Yet Grandison refuses the easy move again, saying he must restrain himself from hitting these would-be helpers. Grandison’s stubborn refusal to take the win has Dick fantasizing about “assassinating” the man, but he tries another play instead. He leaves Grandison alone with a stack of cash with the advice to “enjoy your liberty while you may.” When he returns, there is Grandison.

Dick has removed one barrier after another to allow Grandison to leave and can’t guess why Grandison stays. He then draws an interesting conclusion: Grandison really is just that loyal. He knows “his true place in the economy of civilization.” This conclusion is mystifying to Dick, who can’t see Grandison as an ordinary man motivated by the same desires and hopes that motivate him—at least not yet.

Dick’s final play is to take Grandison to Niagara Falls, ostensibly to view the grand scenery but really to set Grandison’s feet on the free soil of Canada. Yet Grandison refuses to run, choosing to nap by the Falls instead. Since Grandison won’t play his game, Dick takes matters into his own hands and, readers can infer, pays two Canadian men to take Grandison and keep him in Canada, while he abandons the scene.

What Dick hasn’t yet realized is that Grandison has been playing all along, but according to his own rules. That is, he has countered Dick’s moves as a way to buy time and develop a more ambitious plan.

As the story moves toward its climax, Dick overcomes Charity’s opposition and is honeymooning with his beloved on the day that Grandison arrives home, exhausted and near starved, to make his final gambit. Dick immediately feels suspicious of his “improbable” story and suggests that a “more likely explanation” should be sought. But his father, vindicated by Grandison’s escape from freedom, cuts his intelligent son off. A few weeks later, when Grandison and his family are nowhere to be found, the story reaches its climax. Grandison has escaped after all, but he’s also ensured the safety of his entire family. Interestingly, Dick disappears from the story at this point. He has drawn his conclusions about how and why Grandison finally embraced the chance to be free, and it is left to the outraged colonel to chase his “vanishing property,” during the story’s brief falling action, to Lake Erie, just in time to see their escape completed and the story’s conflict fully resolved.