One passage that relates to money, dishonesty, carelessness, hypocrisy, and the American dream is the scene in Chapter 5, in which Gatsby shows Daisy his house. This scene climaxes in Gatsby throwing his shirts on the bed while Daisy cries.
Throughout the reunion, he points out his obvious trappings of wealth in an attempt to impress Daisy. The shirts are no exception. He finishes the tour of his ostentatious mansion by desperately offering her his clothes:
[He] began throwing them, one by one, before us, shirts of sheer linen and thick silk and fine flannel.… While we admired he brought more and the soft rich heap mounted higher—shirts with stripes and scrolls and plaids in coral and apple-green and lavender and faint orange, with monograms of Indian blue. Suddenly … [Daisy] began to cry stormily.
“They’re such beautiful shirts,” she sobbed.… “It makes me sad because I’ve never seen such—such beautiful shirts before.”
At both the first meeting and the tossing into the air of Gatsby’s shirts, Daisy cries. Gatsby deludes himself into thinking it's because Daisy loves him, but in reality, she is revealing her shallow obsession with materialism. Frankly, for her, it could be anyone she's crying over, as long as he owns "such beautiful shirts."
Although Gatsby is deluding himself here, some part of him knows that Daisy will never be the same for him. An illusion has become reality, and on some level he understand that's not what he wants. He states that she has a green light “that burns all night” at the end of her dock. He directly admits that “the colossal significance of that light had now vanished forever,” for the real Daisy, in contrast to the idealized Daisy, is no longer an “enchanted object.” The enchantment had become his total being, had consumed him—no human could have measured up. Thus his American dream is shattered. He has all the wealth anyone could want, but for what? He has been destroyed by his own dreams.
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