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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