Harlem Shuffle (novel)

In 1959, Ray Carney lives in Harlem with his wife Elizabeth, with whom he is expecting a second child. Although descending from a criminal family, Ray makes his living working as an upstanding furniture salesman on 125th Street. However, he occasionally fences stolen goods through his furniture store, including those from his cousin Freddie. Whereas Ray has steered his way toward an honest living, Freddie is descending into Harlem's criminal underworld. Freddie volunteers a reluctant Ray to fence the stolen goods in a robbery of the Hotel Theresa he and his associates, Arthur, Pepper and Miami Joe, are planning, to Ray's fury. However, the heist goes wrong after Miami Joe kills a hostage, leading the group to run afoul of Chink Montague, a mob boss whose territory includes the hotel. The group discovers they stole a necklace intended for Montague's girlfriend and force Ray to fence the stolen goods, to his displeasure. Initially unsure of what to do, Ray decides to tell on Arthur to Chink and warn the former. However, Freddie later tells him Arthur was murdered. Pepper and an unwilling Ray search for a missing Miami Joe, who pursues the latter to his furniture store after being caught and reveals his intentions to betray and kill his team. Pepper kills Miami Joe and leaves Ray to dispose of his body. A month later, Pepper gives Ray the necklace, which he sells a year later and begins accepting his illicit activities.

In 1961, Ray has been paying protection money to Chink and bribes police detective Munson to overlook his fencing since the Hotel Theresa heist. Freddie lives with Linus, a white man and Ray speculates he is involved with Biz Dixon, a drug dealer. Ray unsuccessfully bribes Winifred Duke, a banker, to join the Dumas Club, a prestigious Black social club, to his anger. Plotting revenge against Winifred, Ray schemes to have Winifred photographed in lewd positions with a sex worker, Miss Laura, and distribute the photos to a newspaper. Miss Laura agrees on the condition Ray eliminates her pimp, Cheap Brucie so he informs Munson about Biz Dixon in exchange for the Cheap Brucie's arrest. This leads to Freddie, Biz Dixon and Cheap Brucie getting arrested. A newspaper publishes the photographs and Winifred's past wrongdoings become public knowledge, causing him to flee. Pepper discovers Ray's exploitation of him in his revenge plot, enraging him. Ray begins embracing his criminal behavior more fully.

Three years later, during the Harlem riot of 1964, Freddie visits Ray's store and asks him to hide a suitcase in his safe. Chink's men accost Ray, demanding Freddie's location, prompting Ray to go to his apartment where he discovers Linus has fatally overdosed. Police officials interrogate Ray about Freddie's relation to Linus' death. Ray, now a member of the Dumas club, learns from Pierce, another member, Linus' family, the Van Wycks run a real estate empire and use violence against perceived enemies. Ray opens the suitcase from Freddy and discovers an emerald necklace alongside papers. Freddie explains he and Linus sneaked into the latter's father's mansion but were caught and that he fears their retaliation following Linus' death. Ray enlists Pepper to watch his store while he gets rid of the emerald necklace but gets betrayed by the jeweler who alerts the Van Wyck's lawyer, Ed Bench. Bench possesses the necklace and negotiates the safe's contents for Freddy's freedom. The exchange occurs in an unfinished Van Wyck office building. Pepper kills Bench's henchmen after seeing they brutally beat Freddy for negatively influencing Linus. Ray hastily completes the exchange and rushes Freddy to the hospital where he succumbs to his injuries. Eighteen moths later, Ray reflects on the Van Wycks' motives and the nature of New York City.