Gatsby's personality

Though Nick was first taken with Gatsby's seeming purity and optimism, Gatsby remains enigmatic and not entirely trustworthy. Gatsby's own account of his illustrious past seems comically exaggerated. His readiness to provide evidence to corroborate his story is itself suspect; an honest man, one imagines, would be insulted by Nick's skepticism.

The introduction of Meyer Wolfsheim serves to increase Nick's ­ and the reader's ­ doubts concerning Gatsby's virtue. Nick begins to suspect that the rumors of Gatsby's involvement with organized crime and bootlegging may not be entirely false.

Jordan's story about of Gatsby, by contrast, portrays him as a romantic, forced to worship his lover from afar. Although Jordan implies that there was something in Gatsby's background that caused Daisy's parents to oppose their marriage, it is clear that the young Jay Gatsby was a man of unimpeachable virtue. Fitzgerald draws upon a few centuries of romantic cliché to present Gatsby as the ideal lover: a soldier going off to war, brave and handsome, young and pure. Nick's ambivalence toward Gatsby, in which he finds himself constantly oscillating between admiration and distaste (recall that Nick found the excesses of Gatsby's party repellent), is emphasized in this chapter. The contradiction inherent in Gatsby's character between his guileless optimism and putative moral corruption is also reinforced.

It is important to note that Wolfsheim, the novel's symbolic representative of the "criminal element," is obviously Jewish: Fitzgerald gives the character a number of stereotypical physical features (a large nose, a diminutive stature) that were a staple of racist caricature in the 1920s. During this period, anti-Semitism in America was at an all-time high: Jews, as a result of their "characteristic greed," were held responsible for the corruption of the nation as a whole. Fitzgerald seems to uncritically draw on this racist ideology in his presentation of Wolfsheim; the character is nothing more than a grotesque stereotype.