The fourth chapter of F. Scott Fitzgerald’s novel The Great Gatsby provides undeniable evidence of Jay Gatsby’s involvement in New York’s shady underworld. Before this episode, few clues are provided regarding Gatsby’s nature and past. Although many questions remain at the end of the chapter, Gatsby’s close association with the dangerous character of Wolfsheim shows that he has many secrets to hide.
Even before Wolfsheim begins telling the story of Rosy Rosenthal, Nick suspects that Gatsby may have illicitly earned his wealth and reputation. In the car en route to the lunch with Wolfsheim, Jay desperately tries to provide Nick with a credible, respectable explanation for his fortune. Gatsby claims to have been raised in a wealthy Midwestern family who were “all dead now,” attended Oxford in England, and spent years in the capitals of Europe “collecting jewels.” Gatsby claims that he inherited his riches from his family and became a war hero during the fighting in Europe. Nick is incredulous but struggles to reconcile his skepticism with the medal from Montenegro and the photo from Oxford that Gatsby offers as evidence of his stories.
When they finally meet Wolfsheim for lunch, Nick is immediately struck by the sinister appearance of the man. As he savagely devours his meal, Wolfsheim launches into a story about the shooting of Rosy Rosenthal. Wolfsheim’s presence at these murders and the casual tone with which he discusses the violence proves his intimate familiarity with the criminal underworld and links Gatsby to it by association. Later in the meal, during Gatsby’s phone call, Nick notices that Wolfsheim is wearing an odd form of ivory cufflinks, and Wolfsheim proudly announces that they are the “finest specimens of human molars.” Although Nick initially mistakes Wolfsheim to be a dentist, this detail immediately signals that Wolfsheim is a man to be feared.
Jay Gastby’s close personal relationship to a man like Wolfsheim deepens the mystery of his past and hints that his story of inheriting his wealth is unlikely.