Charity is smart enough to want a man who has accomplished something and smart enough, too, to marry a man over whom she might exercise some power. In agreeing to marry Dick, she gets both, yet only by acting within the confines of Southern womanly behavior. In addition, Chesnutt uses her to expose the hollowness of the ideology of the “purity of southern womanhood.” On the one hand, Charity tells Dick that her “Quaker blood that came from [her] grandmother assert[s] itself when she hears about cruelty in slavery,” and she wishes that “all Sam Briggs’s negroes would run away.” However, when Dick proposes that he would help one of his father’s slaves do just that, she finds the idea “merely absurd,” and when he returns after leaving Grandison in Canada, she only worries that Dick might be sent to the penitentiary and denies having encouraged him to begin: “Why, Dick Owens!...You know I never dreamed of any such outrageous proceeding.” Chesnutt seems to be saying that her “Quaker blood” accepts slavery just fine as long as the masters are not overtly cruel and are instead as patronizingly “kind” as Dick’s father is toward his slaves.
Colonel Owens provides a stark contrast to anyone who has read Uncle Tom’s Cabin, which many of Chesnutt’s original readers probably had. Arrogant and patronizing in the extreme, he mouths every stereotype of the “good slave holder.” In characterizing this slaveholder as foolish rather than harsh, Chesnutt expands the criticism of slavery and racism, for he shows that cruelty exists not just in the physical punishment that might be the lot of slaves but in the system of slavery itself. Furthermore, it is Owens’s “enlightened” view of slavery that enables Grandison to make a fool of the colonel. By the end of the story, this wealthy, educated slave owner is reduced to mere silliness.