Jesus Christ: A great man. Adolf Hitler: Not a great man. George Washington: A great man. George W. Bush: Not a great man. Indeed, the lines of greatness seem to be very clearly drawn. Some men can be undoubtedly cast into either a positive or a negative light. But every once in a while comes a prominent figure that one cannot place. Napoleon Bonaparte, Martin Luther, Charles Darwin in a historical sense, and men like Salinger's Holden Caulfield and Lee's Atticus Finch in the realms of literature. Such is F. Scott Fitzgerald's Jay Gatsby. "Great", according to title, but upon closer inspection, one begins to wonder. Jay Gatsby is not a great man, through his flaws such as obsession, naiveté, and the fact that he is merely a shadow of a man.

Jay Gatsby carries three fundamental character flaws. The first is obsession. Gatsby has two loves: money...