Jay Gatsby's dream is to win Daisy, the love of his life. They meet when they are both young, but the wealthy, sophisticated Daisy refuses his proposal of marriage, because Gatsby is from humble beginnings and has no money. Daisy instead marries Tom Buchanan, a wealthy man who is unfaithful to her. Gatsby, whose real name is James Gatz, decides he must win Daisy at any cost, and he embarks upon a concerted effort to amass wealth.
Five years after Daisy refuses his proposal, Gatsby is a millionaire who owns a fancy mansion in the suburbs of New York City. It is hinted at that Gatsby's money is not earned honestly, and he associates with men who are known to be involved in bootlegging and other illegal activities, like Meyer Wolfsheim. It is the height of the Prohibition era, which took place from 1920 to 1933, and Gatsby's parties are lavish affairs where copious amounts of alcohol are consumed: this alone points to his willingness to bend or break the rules.
This seems to point to a certain recklessness of character; but one could also see the romantic appeal of a man so in love that he will do literally anything, including risk going to prison, to obtain the woman he loves. He follows what many might call a dangerous course, but it is one that brings him success, both financially and personally, if one considers that his wealth attracts Daisy to him once again.
When Gatsby and Daisy meet up again, they almost immediately rekindle their romance. She is impressed by his wealth; in one dramatic scene, he shows her his closet full of shirts, tossing them onto the bed and floor, and she holds them, becoming emotional as she contemplates the wealth that can provide such beautiful clothing. Gatsby surrounds himself with beautiful things, because he knows Daisy will like them. He goes out of his way to decorate his house in a way he thinks will please her. Gatsby becomes well-versed in this wealthy and sophisticated lifestyle; despite the poverty of his youth, his obsession with Daisy compels him to become the rich and admiration-worthy man that he thinks she will leave her husband for.
Gatsby gets so caught up in this youthful fantasy that he loses sight of the fact that Daisy is actually very shallow and not really worth sacrificing his integrity. His ability to become so wealthy so quickly in pursuit of a woman who rejected him because "rich girls don't marry poor boys" suggests that he might have indeed been capable of being a great man, if he had been motivated by something more than a desire to impress a materialistic lover. In the end Gatsby achieves great wealth, but not wisdom.
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