Jay Gatsby is morally ambiguous because of the kind of work he does. He's a bootlegger, participating in and profiting from the illegal production and distribution of alcohol during Prohibition. From 1920 to 1933, such activities were illegal in the United States. While Gatsby is a sympathetic figure, who seems to desire money so badly because he feels that he needs it in order to win back his former flame, Daisy, the way that he earns his money makes him problematic. One of the novel's themes is the American Dream: the idea that anyone in this country can start with nothing and, through hard work and perseverance, thrive and become prosperous. Gatsby seems, on the surface, to have achieved this dream; he came from a relatively modest home and made himself a millionaire. However, the fact that he has acquired his fortune by illegal means problematizes both the extent to which one might claim that he's achieved the American Dream as well as his character's morality.
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