What is the importance of Gatsby's implied business connection with Meyer Wolfsheim?

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Gatsby is often considered a symbol of the American Dream. The important thing to remember, however, is that the Dream has changed over time and does not represent the same things to everyone.

Fitzgerald's novel is a picture of the 1920's, a period when, as happened forty years later in...

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Gatsby is often considered a symbol of the American Dream. The important thing to remember, however, is that the Dream has changed over time and does not represent the same things to everyone.

Fitzgerald's novel is a picture of the 1920's, a period when, as happened forty years later in the 60's, past attitudes and assumptions were swept away and replaced by new ones. In spite of our egalitarian ideals, much of American society up to the period of World War I had been governed by an upper class not unlike that of the Old World countries. Most wealth was inherited. In Gatsby and the people who surround him at his parties we see a new leadership class of elites, a "meritocracy" which now, nearly a hundred years later, has completely replaced the old owning class. Many of the essential ideas at the heart of our concept of America have altered. Fitzgerald was prescient in seeing the significance of this change early on. But the implication, shown by Gatsby's association with racketeers like Wolfsheim, is that this "new wealth" of Gatsby and others is in some sense illegitimate.

Gatsby is an ambiguous figure. He is flawed but admirable because, whatever his imperfections and however much of his wealth is "ill-gotten," he believes in something good and strives for it. He cherishes Daisy without understanding her or recognizing her superficiality for what it is. Nick comments that Tom and Daisy were disregarding people who "smashed things up," and this is what happens to Gatsby. Fitzgerald presents him, and the Dream he represents, as massive contradictions. The nature of Gatsby's wealth and his association with criminals is a metaphor for those imperfections and contradictions that exist in America as a whole.

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Wolfsheim is one of Gatsby's bootlegging partners.  This is important because it reveals that Gatsby is not as ideal and "great" as he appears.  He hasn't come across his wealth by acceptable means.  Since he doesn't come from money, Gatsby, in his quest for the American Dream, was willing to do whatever necessary to acquire money.  Thus his connection to Wolfsheim who seems to be a bit of a thug - note his cuff-links made of human molars.  Wolfsheim is just one in a long list of dirty little things that Gatsby is trying to cover up as he tries to steal Daisy from her husband. 

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