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Jay Gatsby is possibly one of the greatest tragic heroes in American Literature. His devotion to Daisy paired with his desire to “greenlight" his own future and become a member of 1920’s high society is what drives him to become, as the title suggests, “Great." Students who read the novel will identify with Gatsby’s romantic side, hoping against hope that he will once again win Daisy’s love, even as they despise Tom for his affair with Myrtle. They will see Tom, he of the inherited wealth, the beautiful wife, and the place in society as the novel’s antagonist, and the dirt poor, unmarried, bootlegging and stock market-fixing Gatsby as our hero. There is no doubt that Gatsby is the hero of Fitzgerald’s classic novel. However, students do need a better understanding of just how this man earned his ill-gotten gains and furthermore, how he would have earned them today.
In today’s society, Gatsby might very well be a drug lord or even a member of the Mafia; a kind of Tony Soprano character instead of the suave and cool Robert Redford or Leonardo DiCaprio, depending on which movie version one prefers. It is hard to view Gatsby as a criminal because we identify so strongly with his story and admire his devotion to the love of his life. However, a criminal is what Gatsby is and in today’s society, where some law breakers are admired and even praised by our culture, it is an important teaching tool to show students that this “Great Gatsby" character is not all he seems to be.
Download two or three op-ed pieces, such as those provided in the References section of this article from the New York Times and PBS. View clips from Ken Burn’s excellent documentary on bootlegging in the 1920’s. Then, ask students to analyze what effects Prohibition had on the United States. How did it create a new culture of criminal? How did it lead to a rise in the power of the Mafia? How did it add to the downfall of a party going society? These are all questions students should answer while reading the novel and all ideas that they should focus on when they determine just how great Gatsby truly was.