The Passing of Grandison allowed Chestnut to show the complexity of the relationship of the slave to the master and the view of the free black by the Southerner. Before his trip to the north with Dick Owens, Grandison was the most loyal of slaves according to the Colonel, and could not be swayed by the aboiltionist. That is the only reason why he was sent with Dick to New York instead of Tom. The loss of Grandison was more of a crushing blow to the ego of the Colonel as he thought that he could never abandon his masters.
Dick was right in assuming that even the most fervently loyal slaves would value their freedom above the happiness they thought they had while enslaved. Throughout the story Grandison was given many chances to flee by Dick, but he never took his opportunity. In retrospect, his freedom was probably not something that he wanted to be given, rather, he wanted to earn it on his own terms. Dick and Grandison's sentiment were probably shared by many people during the end of the Antebellum, with slaves believing they were content with their lives, and some young slave owners feeling indifferent towards owning slaves and freeing them.
Dick's lack of motivation was also shared by some in the North and South. While there were radical abolitionists who worked diligently to free slaves and help them establish themselves, many were not motivated to action. Dick was motivated only to impress Charity and probably was not against freeing slaves. He even says that his family can afford to lose one slave and that they have plenty.