What lessons does Holling learn that are directly related to Shakespeare and the stories he reads in Gary Schmidt's The Wednesday Wars?

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Two important lessons that Holling learns are the ambiguity of interpretation and the importance of freedom. These lessons come through clearly in his reading of The Tempest , which becomes particularly intensive as he prepares to play the part of Ariel. On his first reading, Holling is sure that Caliban...

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Two important lessons that Holling learns are the ambiguity of interpretation and the importance of freedom. These lessons come through clearly in his reading of The Tempest, which becomes particularly intensive as he prepares to play the part of Ariel. On his first reading, Holling is sure that Caliban is the antagonist and that he deserves the harsh treatment he has received from Prospero. But Holling develops more sympathy for Ariel as he prepares to play the character. He distinguishes between the two characters in terms of their deserving freedom. Ultimately, he realizes that everyone has the right to freedom and that seeing Caliban only as a villain would require denying him that right. More generally, Hollis applies the idea of resolution to life in general, noting that in real life, a magician such as Prospero is not always available to resolve a crisis. Therefore, we must get used to things not ending happily.

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Throughout Gary Schmidt's The Wednesday Wars, Holling applies multiple lessons found in Shakespeare's plays to his own life. Two of those lessons concern better understanding his father and betrayal.

One of the first plays he reads with Mrs. Baker is The Merchant of Venice. After reading the play, Holling decides that Shylock "isn't really a villain"; he is instead a person trapped by his circumstances ("October"). Holling decides that Shylock had wanted to be a different person but could not because others in society around him "wouldn't let him. They decided he had to be a certain way, and he was trapped" ("October"). Later, Holling applies the lesson to his own father. Though Mr. Hoodhood acts like a villain by ignoring his children's needs and placing his business above all else, Holling begins to see that his father may not really be a villain after all. After his father gets the contract to design the new junior high school, Holling observes that his father gleefully thinks of how Kowalski and Associates will surely go out of business, which will place him in a good position to be given the Chamber of Commerce Businessman award next year too. He sees his father greedily rubbing his hands together, like Shylock, and stops to think if he is this way simply because it's what others expect of him:

I suddenly wondered if my father was really like Shylock. Not because he loved ducats, but because maybe he had become the person that everyone expected him to become. I wondered if he had ever had a choice, or if he had ever felt trapped. Or if he had ever imagined a different life. ("February")

Later, Holling challenges his father by saying that becoming a man has to do with becoming whom you choose to be.

Similarly, studying Romeo and Juliet helps Holling better understand human nature. Soon, Holling feels betrayed by Meryl Lee because her father presented to the school board the design Holling had shown her, the design his own father was working on. At first, Holling decides Shakespeare is trying to show through Romeo and Juliet that it is a part of human nature not to be trustworthy. However, he comes to realize that Meryl Lee had innocently shown her father Holling's drawing because she was proud of it, and her own father had betrayed her. This realization also helps Holling understand that Shakespeare's real message in the play is to show how much human beings struggle when they find themselves "car[ing] about two things at the same time" due to human nature being so very fragile ("February"). Human nature is so fragile that we struggle to figure out where to place our loyalties and trust, and incorrect choices concerning loyalty and trust can lead to tragic consequences. 

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