If we look at the characters Chestnutt develops in the story we find three major personalities. First is Dick Owens who throughout the story is attempting to win Charities love with a heroic deed. His scheme to liberate Grandison is completely selfishly motivated. He does not care for the well being of Grandison, he merely is looking to win the affection of a woman with deeds. Not only that, but he chooses the easiest possible road to Charities affections by plotting to steal a slave from his own father's plantation. The task is simple, hardly dangerous, and places nearly any risk or consequence on Owens. Young Owen is a selfish and lazy man looking for the easy path in life and remains this way for the length of the novel. Secondly, Chestnutt develops Dick Owens' father, the Colonel. The Colonel lives for the glory of himself and nothing more. While he at least was not lazy like his son, he lives to hear praise from others and is blinded by his pride from the flattery of others. He loves to hear his slaves praise him for the comforts he provides and that they are proud to have him as their master, yet he fails to see through the farce of the praise because of his pride. He too is selfish which is evident as he lies to his slaves, especially Grandison, by explaining how terrible it is to be free. The Colonel comes to his ultimate downfall because of his prevailing pride and selfishness. In contrast to these characters, Chestnutt create the personality of Grandison. Grandison is neither selfish nor prideful is his actions. He serves both his masters faithfully until the very day he sees fit to leave. Also in one of the greatest acts of selflessness, he gives up freedom, which he ultimately wants, and risks his life in order that he might return to the plantation and deliver his entire family to freedom as well as just himself.
Chestnutt turns upside down the social order of that era by portraying the slave as the courageous, selfless hero rather than the well-to-do white plantation owner or his son, the heir to a great fortune. Chestnutt wanted to bring about change in the way his audience saw slaves. The common thought in the South was that slaves were property, but Chestnutt portrays them as humans, and not just humans but true men of courage and honor. Both the Colonel and Young Owens fail in their journey to be men, while Grandison, a slave, succeeds.