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Harlem Shuffle is a 2021 crime fiction novel by Colson Whitehead. Set in Harlem during the late-1950s and early-1960s, the novel portrays African American life in New York City during a time of social upheaval. The novel is a follow-up to Whitehead’s 2019 book The Nickel Boys, which won him a second Pulitzer Prize for Fiction. This guide uses the 2021 eBook edition published by Doubleday.
In June 1959, an African American furniture salesman named Raymond “Ray” Carney drives his truck around New York City. Ray is the son of a Harlem criminal named Big Mike, whose influence casts a long shadow over his son. Although Ray wants to show the world that he can run a respectable furniture store, he also secretly deals in stolen goods. At home, his wife Elizabeth is pregnant with their second child, and Ray worries about making rent. Elizabeth’s parents are successful professionals who look down on Ray and his family’s reputation.
After a family meal, Ray goes to meet his cousin Freddie. While Ray and Freddie are close, Freddie lacks Ray’s respectable reputation. At a bar, Freddie tells Ray that he is involved with a gangster named Miami Joe in planning a big heist at the Hotel Theresa. He asks Ray if they can use his store to fence the stolen goods, in return for a cut of the profits. Ray promises to think about the offer but plans to decline. Nevertheless, Freddie and Miami Joe rob the hotel. They take an expensive necklace from a safe deposit box which belongs to a local mobster named Chink Montague, who sends his henchmen out to search Harlem for the necklace. Freddie meets with Ray and shows him the necklace, asking him to help sell it. Miami Joe and the rest of the gang meet at Ray’s furniture store. The gang includes a hardened criminal named Pepper and an elderly safecracker named Arthur. They agree to lay low temporarily but insist that Ray sell the stolen necklace as soon as possible.
After Arthur is murdered, Pepper visits Ray and demands to be driven around Harlem. They search for Miami Joe but cannot find him. Later, Ray spots Joe on the street and ducks out of the way when Joe shoots at him. He returns to the store where Joe is already waiting for him. Before Joe can kill Ray, Pepper arrives and shoots Joe. He tells Ray to get rid of the body. Ray does so and then returns home.
Two years later, Ray is selling more stolen goods than ever before and he has expanded his furniture store. He is offered to apply for membership in the Dumas Club, an African American Ray’s father-in-law is a member, but he believes that Ray is too dark-skinned and from the wrong background to join the group. An influential local businessman named Wilfred Duke implies that he can secure Ray’s membership in exchange for $500. Believing that membership will help him to grow his business, Ray gives Duke the money, though Elizabeth warns him that Duke is a crook. The Dumas Club rejects Ray’s application and, after an angry confrontation, Duke refuses to return the money. Ray begins plots his revenge against Duke. Meanwhile, Ray sees Freddie for the first time in weeks. Freddie is currently staying with his new friend Linus, a young rich white man who spends most of his day getting high. Freddie rejects Ray’s suggestion that Freddie is becoming a drug addict.
Ray learns that Duke visits a prostitute named Laura twice a week. He recruits Laura into his plot and hires Pepper to spy on Duke. Ray executes his plan: He uses his police connection to have Laura’s pimp arrested; she drugs Duke and poses him in a variety of scandalous sexual photographs, and then Ray leaks the photographs to the newspaper. Amid the scandal, Duke disappears from Harlem and takes millions of dollars of stolen money with him. The collapse of his business causes financial ruin for many people; Ray’s in-laws are also affected. Even though his revenge cost a great deal of money, Ray is pleased with the results.
Three years later, Ray’s business continues to thrive. He expands his furniture store and his sale of stolen goods, allowing him to move his family into a much nicer apartment. A spate of protests and riots are spreading through Harlem after a white officer killed a young Black boy, but Ray’s business is not looted. The incident is based on real events surrounding the 1964 killing of 15-year-old James Powell by Thomas Gilligan, a white police officer.
Freddie arrives at Ray’s store unexpectedly and asks his cousin to hide a briefcase. The briefcase contains items that Freddie and Linus stole from Linus’s family, the rich and powerful Van Wycks. The next day, Ray is taken to Chink Montague, who asks him about Freddie. Ray denies everything. He goes to the apartment where Freddie is holed up with Linus. Freddie is not in the apartment, but Ray discovers Linus’s dead body. The next day, two police officers interrupt an important meeting to ask Ray about Freddie and Linus. Later, Ray opens the briefcase. Inside is some paperwork and a very large, very expensive emerald necklace.
The house belonging to Freddie’s mother is ransacked, and Ray knows that Freddie is in deep trouble. When Freddie appears at the furniture store, he explains the heist to his cousin. The theft was entirely Linus’s idea, and they were caught in the act by Linus’s overbearing father Ambrose Van Wyck. Ray recruits Pepper to help Freddie escape and to protect his store. Ray tries to sell the emerald necklace, but he is approached and threatened by Van Wyck’s lawyer. The Van Wycks take the necklace, and Ray escapes. He returns to the store to find Pepper hurt, having fought off two of Van Wyck’s henchman. The lawyer calls Ray: They have Freddie and will swap him for the paperwork in the briefcase. Ray examines the documents which give Ambrose power of attorney over Linus. He agrees to the deal. At the swap, a badly beaten Freddie is placed in Ray’s truck. Pepper kills two henchmen, and they leave behind the documents, fleeing the scene and taking Freddie to hospital. Freddie later dies of his wounds. The Van Wyck family considers the matter closed. Ray wanders through Harlem, reflecting on his recent experiences and growing business.