In chapter 4 of The Great Gatsby, what does Wolfsheim's story about the night they shot Rosy Rosenthal tell you about him?

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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...

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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.

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It shows us that Meyer Wolfsheim is a very unsavory character indeed. That he should brood like this over the death of a notorious gangster clearly indicates that Wolfsheim is of much the same stripe. It's notable that he talks about the friends he used to know, and who used to hang out at the old Metropole, the place where Rosenthal was assassinated. Once again, Wolfsheim is revealing his true nature as a member of New York's extensive underworld.

What's even more revealing is that he's a business associate of Gatsby. Once Nick discovers the close connection between Wolfsheim and Jay, he sees a whole different side to Gatsby, one he'd never seen before. This is his first indication that the phenomenal wealth that this ostensibly urbane, sophisticated millionaire has accrued has come by illicit means.

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In chapter four, Nick discovers more about Jay Gatsby's true identity when he travels with him into New York City and joins him for lunch, where he meets Gatsby's shady business partner Meyer Wolfsheim. When the party initially sits down to drink some highballs, Meyer comments that he enjoys the restaurant but likes the old Metropole across the street better. Wolfsheim proceeds to comment that the old Metropole is "Filled with faces dead and gone" and reminiscences about the night that his friend Rosy Rosenthal was shot and killed outside the restaurant at four in the morning. Nick recognizes the tragic story and recalls that four of the men responsible for Rosy Rosenthal's death were executed. The fact that Meyer Wolfsheim was close friends with Rosy Rosenthal reveals that he is a member of the criminal underworld. Jay Gatsby's affiliation with a criminal like Meyer Wolfsheim, who was friends with Rosy Rosenthal and fixed the 1919 World Series, are clues that Gatsby amassed his fortune through illegal means.

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In Chapter 4 of The Great Gatsby, we are introduced to Wolfsheim. He is a shady character, who seems to be close with Gatsby. We get the first taste that Gatsby may not be as innocent as he wants other people to think he is. Wolfsheim tells Nick the story of the night he was present at the killing of Rosy Rosenthal, a known gangster, showing us that Gatsby has been surrounded by these kind of people. 

"Filled with faces dead and gone. Filled with friends now gone forever. I can't forget so long as I live the night they shot Rosy Rosenthal there."

This is the first time we begin to see Gatsby as having a secret. There have been rumors flying around about how he got his money, but now we see that he may have dealings with gangsters. We are introduced to this idea early, and the questions follow throughout the novel. We are never really aware of how Gatsby has made his fortune, but by this one event, we begin to think that it may not be in a honest way. The mysterious life of Gatsby pulls us in from the very beginning and we want to think the best of him. We are now seeing a side to him that may not be so forgiving, after all.

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The story that Wolfsheim tells Nick about his presence during the shooting of Rosy Rosenthal, a famous gangster, clearly links him to the arena of underworld crime and presents him as a shady character. Of course, the real purpose of Wolfsheim is to taint the shining purity of Gatsby in the same way. Wolfsheim's involvement in the "making" of Gatbsy clearly suggests that Gatsby has made his wealth through illicit means. When he is so closely related to a character who is familiar with famous gangsters, has fixed the world series and uses human molars as cufflinks, we as readers, just as Nick does, suspect that Gatsby's meteoric rise to wealth and fame is due to some form of illicit activity.

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