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Gatsby's role in the novel is to illuminate the life of the wealthy in the 1920's and the extremes which some took to achieve the American Dream. His ladder climbing had a double-edged sword since he only wanted wealth to impress Daisy and to win her love. However, for all her shallowness and "full of money" voice, she could not love someone whose wealth was achieved in a less-than-honorable profession.
While we do not know for sure that Gatsby gained his weath through the illegal activity of bootlegging alchohol, it is certain that his dealings were somewhat shady since he was in close contact with Wolfsheim. The air of mystery that surrounds Gatsby from the beginning of the novel (rumors of his having killed a man, or being an Oxford man, or spying in the war) doesn't help his case for being a man of honorable means.
His death is fitting then, since he uses illegal means to gain his wealth, but in doing so he loses Daisy. He is killed as a matter of misunderstanding (Tom intentionally misleads Wilson to Gatsby) thus causing even more mystery and shadow to be cast on him as a member of the nouveau riche. This sort of dishonor could never touch Tom from the old-money bunch.
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