Ray grew up in a family of petty criminals but tried to rise above his roots. He opened a furniture store in Harlem that catered to the local African American neighborhood. He is mostly an honest businessman, but he occasionally purchases items that he knows might be stolen. He is drawn into association with various criminals and crooked cops and tries to balance an honest life as an upstanding family man, while protecting himself from the unsavory elements of the community.
"Harlem Shuffle" consists of three medium-length stories, set about two years apart, each involving a crime that happen around Ray. It is less about the crimes themselves than about Ray's reaction and his reluctant involvement. We get a taste of Harlem during a turbulent decade, including riots sparked by the police shooting of a black youth. I imagine Whitehead writing about these riots as he listens to news of the public reactions to George Floyd's killing.
"Harlem Shuffle" lacks the heavy social commentary of Whitehead's preceding two works. Instead of slavery and abuse, we get small-time hood Cousin Eddie and a couple of gangsters. But we also get a solid character study of a man trying to survive in an immoral world. Ray is a flawed protagonist striving to balance a double life - walking the line between his climb into respectable society and his appeasement of the criminal elements in his life. He struggles because, although he is college-educated and upwardly mobile, society's rules are different for him than for the rich and powerful and white people of New York City.
As Whitehead puts it, Ray is "only slightly bent when it came to being crooked"