A professional slight kicks off Colson Whitehead’s third crime caper. Harlem merchant Ray Carney has just wrapped up an interview with a furniture magazine he adores when he’s called downtown to meet with an, ahem, associate. Carney, who moonlights as a fence, assumes the rendezvous will engender some new criminal opportunity, but it’s a trap. His colleague is a hostage, and the armed captors don’t initially recognize Carney as a fellow crook. “Don’t want to beat up the janitor,” one says after Carney is identified—a baldly racist remark. The quick-thinking salesman manages to wiggle out of the setup and save his partner, but the encounter nettles him. “He had rebuilt his store at considerable financial and psychological cost, received an industry honor, and in five minutes these white men had wrung all pleasure from his victory,” Whitehead writes. “He was fucking Regional Dealer of the goddamn Month,” Carney thinks to himself, setting the record straight.
Vocational pride plays a large role in the conclusion to Whitehead’s Harlem Trilogy. After two decades of crooked escapades, many nearly fatal, Carney has a chip on his shoulder. He had “grazed upon the feasts of middle-class comforts, and had lately acquired a paunch.” His accomplishments in furniture sales don’t capture his overall arc though. Carney’s a successful regional dealer of both couches and contraband, and neither career could exist without the other. But he can’t put “Fencing Since ’59’” on his rebuilt 125th Street storefront, an omission that is slowly eating at him. Hence his rather funny response to being mistaken for a janitor while held at gunpoint. In Cool Machine, he seeks a unified theory of himself, executing schemes for the loot and the laurels as 1980s New York City rumbles around him.
This existential current adds a new dimension to the historical trilogy’s themes. Under the guise of breezy pulp, Whitehead has written a sprawling systems epic attuned to the racialized churn of New York City commerce and real estate. Each novel has focused on a decade in the lives of Carney and New York City, beginning with Harlem Shuffle, which spans 1959 to 1964, and Crook Manifesto, which stretches from 1971 to 1976. The first book took the Civil Rights Movement as a backdrop for a grubbier form of striving, Carney and crew working odd angles as the city stunted Black mobility. The second used the political, financial, and drug crises of 1970s New York to dramatize the difficulty of getting by. Carney and Pepper, his wily bruiser, navigated shifting criminal and cultural landscapes, their hardened views in tension with the metamorphic city. In both novels, Whitehead presented “jobs”—that classic euphemism for criminal schemes—as sweaty, taxing affairs. His crooks endure grimy workspaces, long hours, annoying bosses, and ambient violence, their fortunes attainable only through labor and pluck.
That focus continues in Cool Machine, set between 1981 and 1986. But Whitehead spotlights careers rather than jobs, tracing the long tails of his characters’ grifts, and the city’s. While maintaining the streetwise sensibility of the series’ earlier installments, he revisits key metaphors, analogies, and incidents, layering Cool Machine with both the material history of New York and the personal revelations of his characters. The book is haunted and pondering, the narrative constantly posing questions about community and working life from the perches of middle and old age.
What value does a lifetime of striving, both crooked and straight, produce? Do the skills criminals master prepare them for retirement? Are they even fit to retire given their bloodied hands and strained relationships with regular folk? Their city is subterranean, dark, and lawless, and in it the seismic forces of capitalism, racism, and public corruption are unmitigated. How does such a place become a home?
Carney isn’t the real target of the trap he walks into. The men who lured him, two gruff Bostonians named Buzz and Orson, seek Uncle Rich, a famous Harlem thief who double-crossed them and made out with a sapphire that Carney ended up fencing. Carney had no clue he’d met the legendary bandit, but the jewel connects him to the feud with Buzz, and he needs to work quickly to extricate himself. Buzz, liver-spotted and round of belly, strikes him as violently unforgiving. Carney likens him to a plumber “who comes back when you aren’t home to strangle your parakeet if you stiff him on the bill.”
Carney ends up getting more involved in the beef, stumbling into a kind of criminal internship. Despite the heat from Buzz, Uncle Rich, who’s nearing the end of his career, brings the furniture dealer in on his final jobs. The Harlemite is one of Whitehead’s most memorable inventions. He’s subverted tropes throughout the trilogy, and Uncle Rich epitomizes that enduring sense of play. The final score is often a Hail Mary play in heist stories, concocted by the desperate and almost guaranteed to incur heavy losses.
Uncle Rich, a kooky trickster in his sixties who once faked his death, plans to pull two final jobs. He’s got none of the fatalism of the standard noir criminal mastermind though, and is often jovial. He’s a worldly aesthete and a working man who appreciates a good hot dog, both manager and coworker, hands-on despite his age and expertise—the Godfather as cool unc. In Carney, he recognizes a kindred spirit: “You don’t ask about the stones, or the man who beat your friend. You want to know the lore. It’s nice to see,” he says when Carney fills him in on Buzz’s pursuit.
He gives Carney the lore and a raison d’etre as they outmaneuver Buzz in preparation for the big scores, one of which involves nabbing a Jesse Owens Olympic medal. Under the tutelage of Uncle Rich and his crew, the furniture salesman slowly sees himself and the city anew. He admits that money isn’t his true motive, nor is stability for himself and his family, which he risks every time he churns a stolen good.
Standing on a train platform, Carney ponders a racy ad for Triumph cigarettes, a poster for Escape From New York, and a mural riffing on The Spirit of ’76 that he’d wanted for his store before it was firebombed:
Instead of a straight re-creation of the famous painting, his three musician-soldiers strode out of the ghetto. Worn down, beaten down, but playing on, past the ruined lots and burned-out tenements, fife and drums mixing with the screams and musket fire of battle. The arson job had put the kibosh on that idea, but Carney liked to turn it over in his head occasionally, wondering how many of the Harlemites who turned the corner of 125th Street recognized their own striving in that scene. Escape from New York? There was nowhere to go. Better make the best of it.
Carney’s previously been keen to compartmentalize these tangled urges: “More crooked in one direction and more legit in the other—careful you don’t split yourself in half Carney,” Whitehead wrote in Harlem Shuffle. But this triptych of advertising, pop culture, and homespun patriotism offers a vision of reconciliation, Carney’s divided selves in harmony. As Buzz bears down on Uncle Rich’s crew, Carney, typically the guy who gets involved after the job goes down, gets his first taste of the frontlines and loves it. His diligence doesn’t go unnoticed either. Uncle Rich silently praises Carney as they execute their plan, acknowledging his craft and focus: “Yes, the fence was working out fine. A cool machine.”
Like its predecessors, Cool Machine is divided into three novellas that each take place in a different year. The structure makes the books episodic, with one scheme and its particular players driving each section, but also can stunt the momentum as the story repeatedly resets. That’s still somewhat the case in Cool Machine, which follows Pepper in its middle novella, but the framework is more rewarding this time, as Whitehead actively threads together the stories. If crime is a canvas for Uncle Rich and Carney, a means for self-expression and actualization, for Pepper it is toil, and following him after the high of the first novella offers a sobering contrast.
A World War II veteran who ran with Carney’s late father Big Mike, Pepper is Whitehead’s wry and subtly moving take on the hardboiled hood. First introduced in Harlem Shuffle, he resides cozily in the underworld, and Whitehead often uses that immersion for comedy. Pepper, constitutionally intimidating and alert, always sticks out. He calls normal people “civilians,” and in one exchange, in which a character asks if he’s a mass murderer, he replies, “What’s mass?”
In Cool Machine, Pepper, previously a source of bottomless might, is introduced as severely overworked. “He had gutted, garroted, grappled with his enemies, and been brutalized, bludgeoned, and manhandled in turn,” Whitehead writes. “Shot and stabbed, half strangled and wholly concussed. Beaten with bats, chains, and a hardware store’s worth of ad hoc weapons; thrown out of cars, thrown out of many types of moving vehicles, tossed into pits, ditches, and ruts; and one time even subjected to a modern update of an ancient Aztec torture ritual (this was in Delaware).” The irony is as grim as it is humorous: Work has been steady for Pepper, but so has pain. He’s got no paunch for all his efforts, just aches.
His biggest ailment is an undiagnosed stomach issue, which stalks him as he gets embroiled in a shady art deal on the Lower East Side. He’s hired by a friend of Carney’s wife Elizabeth as a bodyguard, but when the guy is robbed, the role quickly expands into private eye, interrogator, and funnily, art appraiser.
The New York of 1983 is foreign to the veteran goon, the streets strewn with graffiti and refuse, the youth decked out in freaky hairdos and clothes, the music unsettling. The demographic breakdown at his favorite bar skews “maybe seventy-thirty yuppie-crook” and it no longer serves his favorite beer. But Pepper finds his way through the alien city, teaming up with LJ, the mohawked and combat-booted assistant to an art collector, to track down a man, a suitcase full of money, and a Fang mask.
That classic chase-the-Macguffin setup is a con. The novella turns out to be the most experimental in the trilogy, full of psychedelic textures and jagged juxtapositions of text and narrative. Pepper has been expanding his vocabulary via a “Word-a-Day” calendar, and the terms pop into his head as he rummages around the Lower East Side with LJ. Whitehead writes the words in all caps, and they’re typeset outside of paragraphs, making them eye-catching as graffiti. Meanwhile, sardonic “headlines” from a SAMO-like street artist named Daily Newz are plastered across Manhattan, and also get typeset outside of the paragraphs. As do words from assorted signs, wheatpastes, and eventually a film. The result is a kind of psychogeography of Pepper and downtown New York, man, culture, and matter smearing together, clashing.
As the plot ramps up, coming to involve a sadistic hired gun from out of town, a figure from Pepper and Carney’s past, and worsening stomach pains, the old crook considers bailing. “He wasn’t the thief he used to be,” Whitehead writes plainly. But in a pivotal scene that wryly takes place on a toilet where Pepper seeks refuge from his punishing cramps, the words on the streets and in his head swirl into a revelation that leads him to the mask. His New York is threatened, cruel, dilapidated. But for downtown weirdos and uptown killers alike, opportunity still lurks.
In 2021, before the release of the first book, Whitehead pitched the trilogy as a reprieve from The Underground Railroad and The Nickel Boys. “After the darkness of the last two books, the levity, Carney’s humble charm, is fulfilling a psychological need for me,” he told The New York Times. “I could explore the world in a different way, that’s not tied to these terrible systems of capitalism and institutional racism.” This has been true in a way. The narrative voice of the Harlem Trilogy novel is slicker and wackier than those Pulitzer-winning books, more deadpan and acerbic. But Whitehead has not truly changed his tune.
The third novella of Cool Machine, set in 1986, centers on several institutions: family, the mob, City Hall. Robert, son of Carney’s cousin Freddie, who died in Harlem Shuffle, has gone missing. He was the last person to see his dead employer, a lawyer plugged into the city’s political machine, and the cops and the Cosa Nostra start sniffing around. Carney catches déjà vu: Freddie was also once in the crosshairs of cops and gangsters, and he didn’t make it out. Even worse, Carney played a role in Freddie’s fall despite them being close as brothers. He considers Robert his nephew, and finding the young man his duty.
That mission sends Carney on his own psychogeographic odyssey through the city. As he hunts for Robert, he dreams thrice of past apartments and has conversations with Freddie’s ghost, à la A Christmas Carol. He visits a chicken place that burned down in Crook Manifesto and has been reopened by the late owner’s less accomplished niece. It smells of “leftover oil.” He meets Pepper at their old crook bar, which has now been completely yuppified. “The kitchen,” Whitehead writes, “formerly reserved for after-hours beatings of snitches and double-crossers, was back in operation and serving burgers, buffalo wings, and stuffed potato skins.”
The change is jarring, but not unwelcome: Pepper’s girlfriend Blossom compliments the improved environment, as does Pepper, who no longer drinks. “Inflammatory,” he responds when Carney offers a beer. Pepper doesn’t even live in the city anymore; following a much-needed stomach surgery, he’s decamped to despicable Delaware, and comes to town only to help Carney find his nephew. Without becoming an apologist for gentrification, Whitehead admits its fringe benefits, among them a sharpened eye and the capacity to form new connections to old spaces.
Even the mobster antagonist, a retired killer nicknamed the Rabbit because of how quickly he fled the scene of his first hit, finds himself struck by the altered city. His nephew Junior is the killer of Robert’s employer, and because the hit was not authorized, the Rabbit should give him up per mob rules. But as “an old man who’d do anything for his nephew,” he decides to help Junior find Robert, who witnessed the murder. He largely resents ’80s New York. The bulletproof glass at restaurants makes shaking down Black people “like a fucking dessert cart, you want to grab one but you can’t,” he scoffs. Tompkins Square Park, where he once cooled off after breaking a man’s jaw, is a “real shithole now.”
In these competing impressions of and journeys through the city, Whitehead resists a single narrative of New York. It is a cauldron of miseries and a homeland, a hunting ground and a cool machine, a place where even killers and crooks can retire, can commiserate lives lost and enriched. This multiplicity is a pet theme for Whitehead, who once wrote an essay collection on the city, and has set other novels in it. But the Harlem Trilogy has paired the rhapsody with the grit in ways he’s only hinted at before, the romance always followed by a slug to the chin.
In the final act, having located Robert and realized how much institutional might is aimed at the young man, Carney pitches the mob: He’ll give up all his ill-gotten cash in exchange for Robert’s freedom. He gets the idea after recalling a question from Uncle Rich—“What do you value?”—and his answer is family, a layered concept for Carney. He was once ashamed of crime being the family business, reluctant to let his crooked and straight lives overlap, and desperate to unravel them whenever they did. But the pitch draws on both backgrounds. It’s his own final job, the culmination of his furniture store being launched with blood money he found in Big Mike’s truck and Carney truly loving sectionals and coffee tables. It’s a harebrained scheme only he, father, uncle, and veteran salesman and fence could make.
That bespoke sense of finesse is the heart of the Harlem Trilogy. Whitehead doesn’t depict the trait as only cool or guile. He presents it as craft: skill and experience put into action, knowledge applied by hook or by crook. Carney refuses to be called a janitor because he’s dirtied his hands another way. In that last parley, the consummate professional finally gets his flowers.
