This article explores F. Scott Fitzgerald's drawing of the character Jay Gatsby in conjunction with Pierre Bourdieu's theory of the habitus. It seeks to explain why Jay Gatsby has failed at his attempt to maintain wealth, love interest, and even his life. It describes the social and economic realities that make up the conditions of class status and character behavior that lead to Gatsby's lack of survival. The article argues that the social structures and relevant practices of economic status in literature and everyday life are products of inculcated sociopolitical structures and substructures. Characters like Jay Gatsby are governed by, and sealed within, an unchanging class structure regardless of upward mobility. Much in the fashion of Bourdieu's habitus, Fitzgerald's Jay Gatsby plays out his failure though the author's own unconsciously inculcated disposition. Gatsby cannot help but fail. Fitzgerald renders the class habitus through ideologically based cultural goods in the form of physical bodies and the trappings of wealth, showing these through the leitmotif of the American Dream. As such, Bourdieu's theory of the habitus and the social economy of cultural goods is deeply written in the discourse of Jay Gatsby's conflict just as surely as it reveals Fitzgerald's own struggle with class status.