Ray Doesn't Want to Become His Father (Dramatic Irony)
At the beginning of the novel, the narrator explains that Ray tries very hard to avoid being like his father, a known criminal who missed large parts of Ray's upbringing. However, he shows a clear ability to think through complex problems and leverage information and money to his advantage. Little by little, he becomes an increasingly powerful player in New York's criminal world. In this example of dramatic irony, the reader understands that despite his stated aims, Ray actually ends up resembling his father a great deal, showing great skill at his trade.
Pepper Helps Arrest Biz Dixon (Dramatic Irony)
Pepper does several stakeouts at Ray's request. He keeps an eye on both Cheap Brucie and Biz Dixon. He later sees that both of them have been arrested and realizes that Ray was using him to do fieldwork for the cops. In this instance of dramatic irony, the reader sees that Pepper, a hardened criminal, has inadvertently assisted law enforcement.
Wilfred Duke Is An Embezzler (Situational Irony)
When he is first introduced, Wilfred Duke is a high-status banker who runs the Dumas Club. He is viewed, by characters like Leland, as a central pillar of the Black community in Harlem and a figure of great respectability. However, following his fall from grace, it becomes known that he took a great deal of money from the people around him on the promise of various business deals. In this example of situational irony, Duke's respectable appearance quickly gives way to his illicit scams and money-making operations.
Ray Is Betrayed By Moskovitz (Situational irony)
Earlier in the book, Ray changes middlemen. He initially uses a man named Buxbaum to move stolen goods in the downtown area of New York. However, he later moves on to Mr. Moskowitz, a jeweler who works in the diamond district of midtown. He views this as an upgrade, as Moskowitz is less talkative than Buxbaum and also gets him better prices for his items. Buxbaum later gets caught, and goes to prison, but does not give up any information about Ray, while Moskowitz turns him over to the Van Wycks at the first sign of trouble. In this moment of situational irony, the seemingly more "professional" criminal is quicker to hand over Ray to his enemies.
