James finally stands up to his father at the end of Act II.  After being alone with Annie, Helen's behavior has improved considerably, but with the return of her indulgent parents Helen reverts to her tyrannical ways. At the dinner table, the child throws a tantrum when she cannot get her way; her parents are inclined to mollify her, but Annie insists that Helen behave.  After Helen spills a pitcher of water, Annie grabs her with the intention of taking her outside to make her fill it back up, and Mr. Keller moves to stop her.  This is when James stands up to his father, telling him firmly, "Let her go...she's right and you're wrong".

James is a troubled young man and is described as being "indolent".  He is the son of Mr. Keller from his first marriage, and he hides behind a flippant and sarcastic attitude.  James is also intelligent and pragmatic, however, and recognizes what works; he watches the methods Annie uses with Helen, and appreciates the fact that her tenacious firmness succeeds with the child where the permissiveness of his parents fails.  James also admires the quality of obstinancy in a person, as shown in his discussion with his father in Act II about General Grant, who would never give up.  James, despite his faults, is a good person at heart, and when he sees that Annie's methods are effective while his father's are not, he finds the courage to stand up to him, and in so doing, gains his respect.