In chapter 19 of To Kill a Mockingbird, why was Tom's sympathy for Mayella a mistake?

During the cross-examination, Mr. Gilmer asks Tom why he was so anxious to help Mayella Ewell with her chores. Mr. Gilmer then questions Tom why he never asked Mayella for money in return for his services, and Tom instinctively says,

I felt right sorry for her, she seemed to try more’n the rest of ‘em (Lee, 201).

As soon as Tom mentions that he felt sorry for Mayella, he realizes that he has made a serious mistake. Mr. Gilmer repeats Tom's comment and pauses for an extended period of time for Tom's words to sink in. In the prejudiced, segregated community of Maycomb, African American civilians are considered second-class citizens, and it is socially unacceptable for any black person to pity a white person. Essentially, Tom's comment is taboo, and none of the racist white jurors like his comment. Scout mentions that "the damage was done," and Tom loses favor in the eyes of the prejudiced jury. Unfortunately, Tom Robinson becomes a victim of racial injustice after the racist jurors wrongly convict him of assaulting and raping Mayella Ewell.

It is a mistake for Tom Robinson to admit any kind of feelings for Mayella. He should have left out his compassion for her. This gives him a motive to sexually assault Mayella. Of course, Tom was only admitting that he had compassion or pity for Mayella, but this admission puts Tom in a bad light. Now, it appears that he has feelings for Mayella. This is not something Tom should have admitted.

No doubt, the jury is wondering why Tom would have any sentiments whatsoever for Mayella. Why did he feel sorry for her? Who is she to him? Why does he know she has a hard time with the chores around the house? Tom knows too much about Mayella. This puts him in a negative position. Tom passed by Mayella's house each day. He knew she had a difficult time with the chores around the house. Obviously, Tom had had a conversation with Mayella before:

Because he saw she was left alone to maintain the household without any help from her family, he often performed small chores for her. During his testimony, he relates that he felt sorry for the girl. This remark affronts the white men in the jury, who see it as evidence that he is overreaching his social station.

Tom would have been better off to never have admitted any kind of emotions or feelings for Mayella Ewell.

In To Kill a Mockingbird, set in Alabama around 1935, Tom Robinson is an African American on trial for the alleged rape of a young white woman named Mayella Ewell. This is enough to seal Tom's fate, not anything he says. One could say Tom's fate was sealed once Mayella kissed him while her father was looking through the window. Others might argue that the fatal choice was when Tom bolted for the prison fences without allowing Atticus the chance to appeal the conviction. What he says to Mr. Gilmer on cross-examination doesn't do anything more than cause a cringe-worthy and awkward moment. Had someone taken out a gun and shot Tom right then and there for saying he was sorry for Mayella, then one could argue that the comment was fatal. As it is, though, the awkward moment is as follows:

"Mr. Gilmer smiled grimly at the jury. 'You're a might good fellow, it seems--did all this for not one penny?'

'Yes, suh. I felt right sorry for her, she seemed to try more'n the rest of 'em--'

'You felt sorry for her, you felt sorry for her?' Mr. Gilmer seemed ready to rise the ceiling.

The witness realized his mistake and shifted uncomfortably in the chair. But the damage was done. Below us, nobody liked Tom Robinson's answer. Mr. Gilmer paused a long time to let it sink in" (197). 

Even though his comment is not necessarily fatal, this certainly is the wrong thing to say for a couple of reasons. First, the truth hurts. The Southern white people in the courtroom believe that they are better than black people on all accounts, so they were shocked to hear such an uncommonly heard statement. Second, by Tom saying he felt sorry for her, he was pretty much saying he was in a higher position/status in life. It makes one wonder if they were more insulted that he actually was in a higher moral and ethical position in his life than Mayella, or if they were simply offended that he vocalized it. 

The lengthy deliberation and Atticus's comment about it are other pieces of evidence that show Tom's comment wasn't fatal. Atticus says the following when Jem says the jury made up its mind quickly:

"No it didn't. . . That was the one thing that made me think, well, this may be the shadow of a beginning. That jury took a few hours. An inevitable verdict, maybe, but usually it takes 'em just a few minutes" (222).

The jury was going to convict Tom Robinson no matter what awkward comments he said. Atticus even says the conviction was inevitable. Plus, if the awkward comment had been the clincher, the jury would not have taken as long as it did to deliberate. 

Why is Tom Robinson's expression of pity for Miss Mayella in chapter 19 of To Kill a Mockingbird a critical error?

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.

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.

What mistake did Tom make by expressing sympathy for Mayella in To Kill a Mockingbird?

The mistake that Tom made was feeling sorry for a white woman, when whites are supposed to be superior to blacks. 

By feeling sorry for Mayella, Tom put himself above her.  This is the ultimate mistake for a black man in a town like Maycomb.  No matter what, whites are superior to blacks.  This is the way they want to keep things.  Even the poor whites that live in trash heaps like the Ewells are better than respectable, hard-working Tom Robinson.

 Atticus is one of the few people who looks at Tom as a person.  He is fully aware that Mayella Ewell was not raped.  She was beaten up by her father because she kissed a black man.  He is aware that Tom Robinson did nothing wrong except try to help Mayella.  It was Mayella who crossed a line, not Tom.

During his cross-examination, Mr. Gilmer makes a huge victory when he traps Tom Robinson into saying he felt sorry for Mayella.  By that point, everyone felt sorry for her.  Even Scout realizes she is the loneliest person in the world, and can empathize with her despite the misery she has put the Finch family through with her false accusation.

The witness realized his mistake and shifted uncomfortably in the chair. But the damage was done. Below us, nobody liked Tom Robinson's answer. Mr. Gilmer paused a long time to let it sink in. (ch 19)

Mr. Gilmer makes the most of this victory by reinforcing Tom’s low status, raising his own voice and referring to Tom as “boy.”  Sadly, this is enough to convict Tom Robinson of a crime he did not commit.

Atticus was able to establish that Tom was not guilty of raping, or even hurting, Mayella Ewell.  This is why he got the jury to deliberate as long as it did.  However, Tom saying he was sorry for Mayella made him guilty of another crime, feeling sorry for a white woman, which in the eyes of the jury was enough to convict him of the one he did not commit.

The social system of Maycomb doesn't allow for Tom to take pity on Mayella, even if she is derserving. This is because the Ewells, even though they are dirty and sad and inwardly ugly, believe they are superior to Tom and anyone with black skin, and they take it as an insult for someone they believe to be subhuman to take pity on them.

In *To Kill a Mockingbird*, why is Tom Robinson's sympathy for Mayella a mistake?

Tom crosses the boundaries of race and class in an extremely poignant manner.  He, the black man, is supposed to be the lowest of the low, being both black and poor.  Even though Mayella is poor, labelled as white trash, she is still that, white.  Being white puts her above being black in the social hierarchy of the South.  It's the ultimate insult that a black man, whose station in society is as low as it gets, could have the audacity to feel sorry for this white woman.  And to add insult to injury, he is right to feel sorry for her.  It reveals his character, a character which is not allowed for by the rhetoric of his opposers.

Because of the racism during this time, especially in the South, it was degrading for a black person to say he feels sorry for a white person. When Tom says this, he only means he was sensitive to Mayella's situation, but the racist white people took it as Tom putting himself above Mayella. This was not a sentiment that blacks could express about whites since it indicated that the black person was putting himself in a position of superiority over the white person.

Tom's "sin" is that he, a black man, could in any way feel sorry for a white woman.  In the highly prejudicial town of Maycomb, this was akin to saying you were somehow superior. 

You'll find this scene in Chapter 19, when Mr. Gilmer, the prosecuter, cross-examines Tom after Atticus poses his defense, near the very end of the chapter.