In 1959, Ray Carney’s cousin Freddie approaches him with an idea for a heist. The day before this proposition, Carney, a Black furniture salesman who owns a store in Harlem, runs errands in New York City. Freddie sometimes brings “gently used” items for Carney to sell, and Carney tries to suppress his suspicion that they are stolen goods. He takes pride in doing honest business and providing payment plans for the people in his community, even though his family is also financially struggling. Carney is determined to avoid living a “crooked” life like his father, Big Mike.
Carney and his pregnant wife Elizabeth live with their young daughter May in a small apartment. Elizabeth’s parents, Alma and Leland, look down on Carney’s humble upbringing and financial instability—they raised Elizabeth in the affluent neighborhood of Strivers’ Row and believe their daughter settled for Carney. Carney fantasizes about moving into a larger apartment on Riverside Drive. He meets Freddie at a bar and hears his proposition to rob the Hotel Theresa—the most luxurious hotel in Harlem, famous for accommodating Black celebrities. Carney considers the heist, his dislike for crooked behavior at odds with his need for money. He decides to pass on the job.
A few weeks later, Carney hears that the Theresa was robbed. Two men who work for the gangster Chink Montague visit Carney’s furniture store, having heard he sometimes traffics in stolen goods. They are looking for a ruby necklace belonging to Montague, which was stolen in the Theresa robbery. That evening, Freddie appears at the shop, saying his accomplices will arrive soon, since Freddie never told them Carney turned down the job. Freddie and three other men—Miami Joe, Arthur, and Pepper—stole valuable items from the Hotel Theresa’s deposit boxes, including Montague’s ruby necklace. Though the conspirators resolve to wait for the heat to die down before trying to resell the loot, Arthur—who was holding onto the stolen goods—is suddenly killed. Pepper enlists Carney’s help to track down Miami Joe, who he suspects has double-crossed them.
Worried that his association with Freddie will bring harm to his family, a stressed Carney fights with Alma and leaves his apartment to look for Miami Joe. His search is successful, but Joe chases Carney back to his furniture store, trying to shoot him. He has indeed double-crossed them and plans to kill the rest of the team before leaving town. Pepper emerges from Carney’s basement and shoots Miami Joe, killing him. A month later, Pepper sends Chink Montague’s ruby necklace to Carney, who resells it, reflecting that he is a bit crooked after all.
Two years later, in 1961, Carney pays prominent Black banker Wilfred Duke $500 as a bribe for membership in the Dumas Club. Leland Jones—Elizabeth’s father—is a member of the Black social club, which previously only allowed light-skinned members. Since the Theresa job, Carney pays Chink Montague protection money and bribes local law officer Detective Munson to turn a blind eye to his “fencing” side business in stolen goods. Carney hopes the Dumas Club will give him new business opportunities, but Carney’s application is rejected. Furious, Carney hatches a plan to get revenge on Duke for not upholding his end of their deal.
Freddie is now living with a White man named Linus. Freddie takes offense when Carney asks if he is pushing drugs for dealer Biz Dixon. Carney wakes in the early hours to take care of his own crooked business, a time he refers to as “dorvay.” Montague has been sending thieves to pawn their loot at Carney’s shop, meaning business is going well. He sells precious jewels to Harvey Moskowitz, a jeweler who teaches him how to recognize a piece’s worth.
The novel reveals Carney’s plot against Duke in a nonlinear fashion. Pepper follows Duke for Carney and discovers the banker visits a sex worker named Miss Laura twice a week. Miss Laura agrees to betray Duke if Carney gets rid of her pimp, Cheap Brucie. Carney trades information on Biz Dixon’s drug business (obtained by Pepper) to Detective Munson in exchange for Cheap Brucie’s arrest. Miss Laura lures Duke to her apartment, drugs him, and photographs him in lewd positions. When these photos are published in the Harlem Gazette, Duke’s other crimes come to light and he is forced to go on the run. Biz Dixon is also arrested, as is Freddie, who was with him at the time. Pepper is furious at Carney for trading his information to the police. Carney revels in the satisfaction of revenge, embracing his crooked nature more fully.
Three years later, in 1964, Carney moves his family into an apartment on Riverside Drive. Violent riots have broken out in Harlem after an off-duty White police officer murdered James Powell, a Black teenager. Carney’s furniture store was untouched by the violence. Freddie visits Carney’s store and asks to stash a suitcase in his safe. The next day, Chink Montague and his men accost Carney, looking for Freddie. Afterwards, Carney goes to Freddie’s apartment and finds Freddie’s friend, Linus, dead of an overdose.
Two police officers interrupt Carney’s meeting with prospective furniture seller Mr. Gibbs to question him about Freddie in relation to Linus’s death. Carney, now a member of the Dumas Club, consults his friend Pierce about Linus’s family, the historically prominent Van Wycks. The Van Wycks run a powerful real estate empire and are known to silence their detractors with violence. Carney opens Freddie’s briefcase and finds a gigantic emerald necklace along with some papers.
Returning to the furniture store, Freddie tells Carney how he and Linus snuck into the Van Wycks’ apartment but were spotted by Linus’s father, Ambrose, after clearing out the safe. With Linus dead, he fears the Van Wycks are looking for him and their stolen merchandise. Carney hires Pepper to watch the store while he tries to get rid of the emerald necklace. Pepper has dinner with Carney’s family spontaneously, and Carney feels the two sides of his identity are coexisting. Moskowitz refuses to sell the necklace and betrays Carney, alerting the Van Wycks’ lawyer, Ed Bench. Bench confiscates the necklace. Carney runs to the store, where Pepper has fought off two more of Van Wyck’s men. Bench calls Carney to tell him they have Freddie and will exchange him for the rest of the safe’s contents. Everyone meets at an unfinished Van Wyck office building. Seeing that Van Wyck has beaten Freddie severely for supposedly corrupting Linus, Pepper kills Bench’s men. Carney hands over the briefcase and rushes to attend to Freddie, who later dies in the hospital. Eighteen months later, Carney reflects on the Van Wycks’ mysterious motives and their role in the ever-changing face of New York City.