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Through Caesar, Cora’s companion for the first portion of the novel, Whitehead demonstrates how slavery and the legal systems that supported it destroy people regardless of how smart and careful they are. Unlike most of the enslaved people on the Randall plantation, Caesar lived the first part of his life in circumstances that encouraged his intellectual development. Mrs. Garner, who enslaved him and his parents, preferred to let them run the house and farm nearly as their own, promising them freedom at her death. Although her false promise ruins his family’s life when they are separated and sold south after her death, growing up with the expectation of future freedom gives him the boldness necessary to attempt escaping Randall, and his literacy and skill at woodworking connects him to Fletcher and therefore to the Underground Railroad.
Caesar is constantly learning new things. While other enslaved people at Randall use the abandoned schoolhouse primarily to meet lovers, Caesar uses it for learning, coming there to read the copy of Gulliver’s Travels he has insisted Fletcher give him, regardless of the fatal danger of an enslaved person being caught reading. For Caesar, reading is a form of freedom. He learns from the book, noting Gulliver’s “guile and pluck” and also his error of forgetting what he has. Caesar learns from the other enslaved people at Randall as well. He chooses Cora for a traveling companion based on what he has learned about her character and her mother’s escape. The knowledge he gains from the hunters allows him to lead Cora and Lovey safely through the swamp. In South Carolina, he adjusts easily to a new life. However, Caesar’s courage, intelligence and determination are no match for the power of slavery. He is worthy of freedom and prepared to seize it, but ultimately, he cannot escape a system built to keep him in bondage until death. Whitehead uses his story to demonstrate the near impossibility of attaining freedom, even for someone like Caesar, who seems well equipped to succeed.
