In chapter 19, when Tom Robinson is on the witness stand, he says that he feels sorry for Miss Mayella. Why is this such a critical error?

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Tom Robinson is a decent man who is capable of sympathy for Mayella Ewell, who he knows is lonely and isolated. She is also likely being abused by her father, Bob Ewell. However, in the segregated South of Jim Crow days, a black man could not express this kind of sympathy for a white woman. In the racial hierarchy that was enforced at that time, blacks were considered to be always inferior to whites. Therefore, black people could not express sympathy for a white person. Such a declaration would upend the racial hierarchy and imply that black people were superior or equal to whites, and that expression was something whites could not accept.

Therefore, while Tom Robinson's expression of sympathy comes from the goodness of his heart, it is a mistake for him to have said such a thing in court. His words imply his own equality with whites, and that makes the whites on the jury uncomfortable and unsympathetic to him.

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The case of Tom Robinson is decided by the prejudice of the jury, not by the guilt of Robinson. When Tom says that he, a black man accused of raping a white girl, actually feels sorry for the girl because of how bad her life is, it greatly offends the white jury members. Within their society, he was as low as it gets, yet he had the audacity to feel sorry for a white person. His comment riles the audience back up, and removes any sympathy they may have felt for him.

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