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One of the major facets of the American dream centers around money and the acquisition of wealth. Gatsby has managed to transform himself into an incredibly wealthy man but apparently has done so in a relatively shady manner, perhaps suggesting that one cannot actually amass that kind of wealth in an honest way, creating one assault on the idea of the American Dream.
A second problem is the fact that, despite having this insane amount of money and being able to spend lavishly, Gatsby cannot actually break into the world of Tom Buchanon and Daisy, he is still kept out because he is suspect and he is "new money."
A third way that Gatsby symbolizes corruption of the American dream is his connection to the gamblers that fixed the world series and the idea that one cannot manage to rise from a relatively humble background without making those kinds of connections to crime and dishonesty.
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