Nick lists all of the people who attended Gatsby’s parties that summer, a roll call of the nation’s most wealthy and powerful people. He then describes a trip that he took to New York with Gatsby to eat lunch. As they drive to the city, Gatsby tells Nick about his past, but his story seems highly improbable. He claims, for instance, to be the son of wealthy, deceased parents from the Midwest. When Nick asks which Midwestern city he is from, Gatsby replies, “San Francisco.” Gatsby then lists a long and preposterously detailed set of accomplishments: he claims to have been educated at Oxford, to have collected jewels in the capitals of Europe, to have hunted big game, and to have been awarded medals in World War I by multiple European countries. Seeing Nick’s skepticism, Gatsby produces a medal from Montenegro and a picture of himself playing cricket at Oxford.
Gatsby’s car speeds through the valley of ashes and enters the city. When a policeman pulls Gatsby over for speeding, Gatsby shows him a white card and the policeman apologizes for bothering him. In the city, Gatsby takes Nick to lunch and introduces him to Meyer Wolfshiem, who, he claims, was responsible for fixing the 1919 World Series. Wolfshiem is a shady character with underground business connections. He gives Nick the impression that the source of Gatsby’s wealth might be unsavory, and that Gatsby may even have ties to the sort of organized crime with which Wolfshiem is associated.
After the lunch in New York, Nick sees Jordan Baker, who finally tells him the details of her mysterious conversation with Gatsby at the party. She relates that Gatsby told her that he is in love with Daisy Buchanan. According to Jordan, during the war, before Daisy married Tom, she was a beautiful young girl in Louisville, Kentucky, and all the military officers in town were in love with her. Daisy fell in love with Lieutenant Jay Gatsby, who was stationed at the base near her home. Though she chose to marry Tom after Gatsby left for the war, Daisy drank herself into numbness the night before her wedding, after she received a letter from Gatsby. Daisy has apparently remained faithful to her husband throughout their marriage, but Tom has not. Jordan adds that Gatsby bought his mansion in West Egg solely to be near Daisy. Nick remembers the night he saw Gatsby stretching his arms out to the water and realizes that the green light he saw was the light at the end of Daisy’s dock. According to Jordan, Gatsby has asked her to convince Nick to arrange a reunion between Gatsby and Daisy. Because he is terrified that Daisy will refuse to see him, Gatsby wants Nick to invite Daisy to tea. Without Daisy’s knowledge, Gatsby intends to come to the tea at Nick’s house as well, surprising her and forcing her to see him.
Though Nick’s first impression of Gatsby is of his boundless hope for the future, Chapter 4 concerns itself largely with the mysterious question of Gatsby’s past. Gatsby’s description of his background to Nick is a daunting puzzle—though he rattles off a seemingly far-fetched account of his grand upbringing and heroic exploits, he produces what appears to be proof of his story. Nick finds Gatsby’s story “threadbare” at first, but he eventually accepts at least part of it when he sees the photograph and the medal. He realizes Gatsby’s peculiarity, however. In calling him a “character,” he highlights Gatsby’s strange role as an actor.
The luncheon with Wolfshiem gives Nick his first unpleasant impression that Gatsby’s fortune may not have been obtained honestly. Nick perceives that if Gatsby has connections with such shady characters as Wolfshiem, he might be involved in organized crime or bootlegging. It is important to remember the setting of The Great Gatsby, in terms of both the symbolic role of the novel’s physical locations and the book’s larger attempt to capture the essence of America in the mid-1920s. The pervasiveness of bootlegging and organized crime, combined with the burgeoning stock market and vast increase in the wealth of the general public during this era, contributed largely to the heedless, excessive pleasure-seeking and sense of abandon that permeate The Great Gatsby. For Gatsby, who throws the most sumptuous parties of all and who seems richer than anyone else, to have ties to the world of bootleg alcohol would only make him a more perfect symbol of the strange combination of moral decadence and vibrant optimism that Fitzgerald portrays as the spirit of 1920s America.
On the other hand, Jordan’s story paints Gatsby as a lovesick, innocent young soldier, desperately trying to win the woman of his dreams. Now that Gatsby is a full-fledged character in the novel, the bizarre inner conflict that enables Nick to feel such contradictory admiration and repulsion for him becomes fully apparent—whereas Gatsby the lovesick soldier is an attractive figure, representative of hope and authenticity, Gatsby the crooked businessman, representative of greed and moral corruption, is not.