Tee Bob Samson is one of the most sympathetic characters in the novel. Even though he is a white man of privilege, being the heir to the Samson plantation, Tee Bob's awakening to the reality of their racist system leads him to kill himself. Even as a children, Tee Bob appeared to be a sensitive child. He followed Jane around in the field checking to see if she was okay. It was upon his request that the Samsons transferred her to the Big House. As a boy, Tee Bob could not understand why his brother, Timmy, was sent away. Tee Bob's ability to relate to and love his brother as children allowed him to develop a genuine relationship outside of race. Tee Bob was supposed to understand as he grew up the basic racist regulations of his society, but his adoration of Mary Agnes demonstrates that he never did. Tee Bob kills himself because he feels that he cannot fit into a society where race defines him and everyone in it regardless of the true content of their hearts.

Although Tee Bob is sympathetic, he still is a member of the white ruling class. His behavior in the novel and even the way that he courts Mary Agnes shows his knowledge of his superiority. As they walk, for example, he rides on a horse—a move that indicates his higher social position. In the moments before his death, though, Tee Bob suddenly sees the way that the history of his family and the South forces him to be something, even if he does not want to be it. Given the history of relationships between Black women and white men, there is no way that Tee Bob can simply love Mary Agnes as person truly loves another. The burden of race and its history always will come between them. Tee Bob's final appreciation of this truth is what finally causes his death.