When it is said that it was done to please a woman, there ought perhaps to be enough said to explain anything; for what a man will not do to please a woman is yet to be discovered. Nevertheless, it might be well to state a few preliminary facts to make it clear why young Dick Owens tried to run one of his father’s negro men off to Canada.
The opening line of "The Passing of Grandison" simultaneously lays out the background to Dick's self-serving motivation to release one of his father's slaves and establishes the story's comic tone. Although the subject of slavery is often treated with utmost seriousness in literature, Chesnutt's 1899 look back on the 1850s takes a lighthearted approach. It is significant to note that Chesnutt's satiric humor doesn't come at the expense of the enslaved characters in the story, but rather at that of the hapless white characters whose racist biases make them fail to see what the clever Grandison is really up to.
"I’ll never love you, Dick Owens, until you have done something. When that time comes, I’ll think about it."
After discussing the heroism of the young Ohio man who went to prison for trying to free a slave, Charity disparages her boyfriend by accusing him of being too lazy to do anything meaningful himself. In this passage, she raises a barrier to Dick and goads him into trying to overcome it. While the comment may have been flippant to her, Charity doesn't realize that Dick is poised to accept her challenge by freeing one of his father's slaves.
"I should just like to know, Grandison, whether you don’t think yourself a great deal better off than those poor free negroes down by the plank road, with no kind master to look after them and no mistress to give them medicine when they’re sick and—"
"Well, I sh’d jes’ reckon I is better off, suh, dan dem low-down free niggers, suh! Ef anybody ax ’em who dey b’long ter, dey has ter say nobody, er e’se lie erbout it. Anybody ax me who I b’longs ter, I ain’ got no ’casion ter be shame’ ter tell ’em, no, suh, ’deed I ain’, suh!"
In this exchange, the colonel has invited Grandison inside to answer a series of questions designed to confirm their relationship as master and slave, superior and inferior. Grandison’s dialect-laden eloquence is an example of how Grandison is clever enough to present himself as inferior to his owner because this recurring humiliation is key to as good a life as he can have on the plantation. While the colonel beams at Grandison's performance of loyalty, he remains unaware that Grandison is merely telling him what he wants to hear.
DEAR FRIEND AND BROTHER:—
A wicked slaveholder from Kentucky, stopping at the Revere House, has dared to insult the liberty-loving people of Boston by bringing his slave into their midst. Shall this be tolerated? Or shall steps be taken in the name of liberty to rescue a fellow-man from bondage? For obvious reasons I can only sign myself,
A FRIEND OF HUMANITY.
Having failed to emancipate Grandison in New York despite many opportunities, Dick tries a new approach in Boston: contacting local abolitionists through an anonymous letter. With this letter, Chesnutt again emphasizes the comic irony of the situation. In order to achieve his goal, Dick cynically adopts the language of abolitionists to disparage himself so that his slave will be kidnapped. The abolitionists receiving this letter would never suspect that the "wicked slaveholder" is the real source of the anonymous tip.
"Oh, Dick, what have you done? If they knew it they’d send you to the penitentiary, like they did that Yankee. ... But I presume I’ll have to marry you if only to take care of you. You are too reckless for anything and a man who goes chasing all over the North, being entertained by New York and Boston society and having negroes to throw away, needs someone to look after him."
Surprisingly, Charity’s response is not what Dick expected. Instead of showering praise on him for his heroic deed, Charity seems upset with him for actually risking his own liberty for that of a slave. Nonetheless, Charity fulfills her coded promise by agreeing to marry Dick—if only to save him from doing something reckless again.
A week after the wedding they were seated, one afternoon, on the piazza of the colonel’s house, where Dick had taken his bride, when a negro from the yard ran down the lane and threw open the big gate for the colonel’s buggy to enter. The colonel was not alone. Beside him, ragged and travel-stained, bowed with weariness, and upon his face a haggard look that told of hardship and privation, sat the lost Grandison.
Dick's rash strategy of paying people to kidnap Grandison comes back to haunt him when the worn-out figure of Grandison reappears at the plantation. In this passage, Chesnutt draws out the suspense—and comedy—of the moment with syntax that saves the mention of Grandison's name for the final word in the final clause of a multi-clause sentence. With this stylistic decision, Chesnutt creates the literary equivalent of the drumroll sound that announces a big reveal.
About three weeks after Grandison’s return the colonel’s faith in sable humanity was rudely shaken, and its foundations almost broken up. He came near losing his belief in the fidelity of the negro to his master, — the servile virtue most highly prized and most sedulously cultivated by the colonel and his kind. One Monday morning Grandison was missing. And not only Grandison, but his wife, Betty the maid; his mother, aunt Eunice; his father, uncle Ike; his brothers, Tom and John, and his little sister Elsie, were likewise absent from the plantation; and a hurried search and inquiry in the neighborhood resulted in no information as to their whereabouts.
Grandison's reappearance restores the colonel's faith in his most-loyal slave, and the slaveholder rewards Grandison with the opportunity to marry Betty and by giving him a more dignified position as a house servant. However, his trust is soon broken when Grandison flees the plantation with his family in tow. With this instance of situational irony, Chesnutt shows that Grandison was merely acting servile all along. He didn't want to find freedom when traveling with Dick because freedom would have meant nothing without his loved ones close.
