What is Gatsby's tragic flaw and how does it condemn him?

Gatsby's tragic flaw is his lack of transparence and his naivete. He believes that he can buy love and friendship, but it is all superficial. He tries to mold his character/personality around the image that he thinks others want to see.

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Gatsby tries to believe in the image he has created - of himself first, then of others. He has become wealthy through dubious means (bootlegging whiskey and gambling) but manages to keep up a clean "preppy" look just the same. He maintains his status by throwing lavish parties but does not seem to really care to much (on a personal level, that is) about the 'friends' he invites. He remains detached from the essential - developing true relationships with "real" people. He is a loner in the crowd:

Only Gatsby, who was relatively unselfish in his life, and whose primary flaw was a naive idealism, could be construed as fulfilling the author's vision of the American Dream. Throughout the novel are many references to his tendency to dream, but in fact, his world rests insecurely on a fairy's wing. On the flip side of the American Dream, then, is a naivete and a susceptibility to evil and poor-intentioned people.

- from http://www.enotes.com/great-gatsby/themes

Gatsby's fascination with Daisy is also on a superficial level. He accepts rather nonchalently her fickle nature as if it were an inherent part of her femininity. He thinks he can somehow buy her out through his money, at least for a while, and does  not even lament the fact that they both reciprocally use each other. His willingness to "take the rap" for manslaughter to cover for Daisy reveals a certain naïve belief that he can beat the system one more time by just playing the role of 'the nice guy.'  In the back of his mind, he might have even entertained the idea that this act would make Daisy indebted to him. Such lack of transparence unfortunately ends up costing him his life. He is murdered by revenge for a "crime" he did not commit.

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