In my opinion, It's depend on the way Steve answer and show his emotion with the judge . And Mrs. O’Brien’s feelings toward Steve is very serious, she asked a question that what do you mean "win" so that is a trick question because in this case, I think "win" mean to go to jail not to die. She is a little bit funny too when she asked that question!
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One can infer that Mrs. O'Brien is very stern with Steve, and believes he is guilty. She is aware of what is to happen, and one can tell that she isn't the fondest of him. She uses a very harsh, business-like tone when speaking to the criminal, and when he asks if she thinks they're going to win, her response is, "It depends on what you mean by 'win.'" This dialogue implies that O'Brien feels that he is guilty, and that the fiery redhead is merely trying to evade the death penalty.
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