How could a real-life person or a character be compared to Jay Gatsby?

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The Great Gatsby by F. Scott Fitzgerald was originally published in the 1920s and reflects the nature of upper class life in New York in that period. To compare Gatsby to a "real life" person means researching the period and milieu to discover historical characters who might have influenced Fitzgerald.

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The Great Gatsby by F. Scott Fitzgerald was originally published in the 1920s and reflects the nature of upper class life in New York in that period. To compare Gatsby to a "real life" person means researching the period and milieu to discover historical characters who might have influenced Fitzgerald.

Gatsby is an example of a type known as the "self-made man" which has very much influenced American culture. The classic self-made men included Benjamin Franklin, Andrew Carnegie, and Horatio Alger, who rose from poverty to positions of wealth and influence. They are often considered exemplars of the "American Dream."

In comparing these to Gatsby, one should focus on how the characters usually cited as examples of the "American Dream" were honest and hard-working, while Gatsby is closer to successful criminal who is not content with simple financial success but wants to remake himself in terms of social class as well. For an academic paper, one might also wish to cite Stephen Greenblatt's Renaissance Self-Fashioning, a work that has been very important in literary studies of the concept.

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A person who jumps to mind as sharing similarities with Jay Gatsby would be Donald Trump. Both are bigger-than-life figures about whom gossip swirls. Both like the grand gesture, the big house, the color gold. Both try to impress people with their wealth. Both have had colorful pasts (though Trump is not associated with criminal enterprises) and both see women as beautiful trophies they can acquire.

While Trump was born to wealth and Gatsby was not, Trump's jump into presidential politics can be seen as daring to aspire to a world to which he was not invited, just as Gatsby's acquisition of wealth was seen by people such as Tom Buchanan as an affront. Trump's rejection by old-line political families like the Bushes can be seen as similar to Gatsby's rejection by old-money, horsey people like Tom and the Sloanes. Both men, Gatsby and Trump, have dared to try to conquer new arenas, to be more than they were when they started out. Both are astonishingly ambitious. Both are seen by some as garish. Both are controversial figures.

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