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In “How to Write,” a parody article published in 2012, Colson Whitehead offers a tongue-in-cheek lesson in creative composition. He mocks the traditional guidance distributed in writing workshops by listing 11 so-called rules (No. 1: “Show and Tell”), which begin straightforwardly and then spin into the absurd. Rule No. 6: “What isn’t said is as important as what is said. In many classic short stories, the real action occurs in the silences. Try to keep all the good stuff off the page.” It’s a bizarre treatise, but the piece ends rather earnestly, reinforcing the notion suggested in Whitehead’s half-silly advice that there are no hard-and-fast rules to writing well and entreating readers to “just be yourself.” That, in short, is the arc of the author’s career: At the start, he deployed humor as a cudgel against sentimentality or contrivance, but in recent years, he’s relented to sincerity, embracing deep feeling and even tenderness. Whitehead tends to use familiar narrative mechanisms (especially those belonging to genres like noir, horror, crime, and adventure) to chart unforeseen sensations or realities. He takes tropes and uses them to rope-a-dope the reader; he springs the traps laid by convention and the strictures of form in order to dictate his own course, to establish new norms.
In particular, Whitehead repurposes ready-made narratives to explore underrepresented areas of Black experience; he consistently commits to the bit and then twists it, finding emotional resonances where you’d least expect them. His first novel, The Intuitionist (1999), a neo-noir, was about a purposefully niche subject: the first Black female elevator inspector in a guild. Apex Hides the Hurt (2006) concerns a “nomenclature consultant” who helped to name a special Band-Aid that blends into the wearer’s skin tone and considers how branding can obscure meaning. Sag Harbor (2009) surfaces a lesser-known Black enclave on Long Island. His 2014 memoir, The Noble Hustle: Poker, Death and Beef Jerky, evolved out of a series of deadpan columns about playing Texas Hold’em during his divorce. The idea for The Underground Railroad (2016), his Pulitzer Prize–winning novel, came from a whimsical childhood question, a cute kids’ joke — “What if the Underground Railroad were an actual train?” — and his other Pulitzer winner, 2019’s Nickel Boys, was inspired by a real-life story in which anthropology students discovered the bodies of Black children killed at the cruel Arthur G. Dozier School for Boys decades after the murders. Cool Machine, out tomorrow, is the final novel in his Harlem Trilogy, and it seems to take the spirit of that sixth writing rule about leaving things unsaid seriously. Along the way, Whitehead celebrates, in deliberately unsentimental fashion, the variety of Black ingenuity and splendor on offer in marginalized circles.
Whitehead is consistently interested in the byways of Black life, and The Harlem Trilogy is no exception. The books’ primary protagonist, Ray Carney, an ambitious furniture salesman with a criminal lineage, has straightened up the family line and mostly flies right. He married Elizabeth, a daughter of Strivers’ Row, that venerable, beautiful district, and graduated from Queens College. In the daytime, he’s an upstanding entrepreneur running a modest store and helping his neighbors furnish their homes with good, dependable pieces on generous installment plans. By night, he’s a fence, helping to convert hot items — jewelry, electronics, rare coins, and medals — along a subversive route. In the first book, Harlem Shuffle, which is set from 1959 to 1964, we learn that “there was a natural flow of goods in and out, and through people’s lives, from here to there, a churn of property,” and he “facilitated that churn.” Carney (the narrator almost exclusively refers to him by his last name), it’s said, is “only slightly bent when it came to being crooked,” but crooked nonetheless. Also in his orbit are a consortium of crooks, including his cousin Freddie, a hip junkie, and Pepper, a taciturn hoodlum who was friends with Ray’s dad, Big Mike, a legendary thief.
Rather than the sparkling monuments of Movement — the dignified sculptures, canonized verses, and righteously remembered works of activism — the trilogy, each comprising three related parts, concerns movement more broadly, movement as a fact of the world, as inviolable as the laws of physics. Whitehead’s criminal coterie is tapped into “the unseen forces that made everything go,” and, like vibrating atoms, these guys carom around the hood: The pimps bounce, the cat burglars slink, and the forgers use ink to transport themselves to other places. The books brilliantly make use of the dual definition of the word caper. Caper: “an illegal or questionable act or escapade.” Caper: “to leap or prance in a playful manner.” This is a world of movers and shakers, and the plots have a frolicking quality that feels complementary to the Bob & Earl song that inspired the title of the first book, Harlem Shuffle. “I am a man!,” the old NAACP signs read. This trilogy asks you to look at the other men in those hallowed archival photos, those slinking away from the camera’s lens; it spurs you to imagine those guys who simply don’t show up in any archive.
At first, Carney scrapes by, participating in small-time jobs — and occasionally larger ones, like a heist of the legendary Hotel Theresa, “the Waldorf-Astoria of Harlem” — to save up for better housing and to help the reckless Freddie, who has no qualms about his hustle. In the second book, Crook Manifesto, which takes place between 1971 and 1976, Carney gets deeper into the black market, as does Pepper, who does security for a Blaxploitation film being financed by a mobster, all while fires rage uptown and across the embroiled city. Cool Machine, which thrums from 1981 and 1986, sees Ray and Pepper in their mid-50s and -60s, respectively. The men contend with age and the bruising impact of harnessing “the secret energies that move the world.”
In the opening part of the final book, Carney encounters a criminal mastermind who makes him wonder what, beyond money, is the motivation for all of his malfeasance. Instead of operating only for financial gain, this expert acquaintance has higher-minded aims, namely the reclamation of a prize once bestowed upon a famous athlete. In the second story, Pepper is tasked with finding a pilfered Ngil mask belonging to the Fang people of Gabon. He’s become an old man, guzzling Pepto-Bismol to aid mysterious stomach trouble and looking forward to the entries in his word-of-the-day calendar, which have become “his morning vitamin, nourishing interior systems even as it famished others. Language was a secondhand jigsaw puzzle. The more words he added, the more he became aware of the missing pieces.”
Here Whitehead’s work of subverting one expectation has paid off, like a lucrative heist: By the time we arrive, it should come as no surprise to attentive readers that Pepper, the lumbering muscle, the clichéd “man of few words” we meet in book one, actually has a deep reverence for language. Readers have come to know that there’s a quiet philosophy under all of that grunting and talking with his hands. Even as one of Whitehead’s occasional jokes threatens to distract in this middle part (there’s a character called “Dee Void,” for example), Pepper’s search for the mask essentially coincides with a search for himself and the African heritage he isn’t connected to. He may not be an intuitionist in the way of Whitehead’s first protagonist, but he tries to trust, and test, his gut reactions. Mayor Ed Koch’s catchphrase “How am I doin’?” becomes a refrain throughout the book, timestamping the plot and mocking the gimmicks of self-serving politicians. But the saying also slyly sets the stage for the men’s existential inquiries; in Cool Machine, Pepper and Carney ask themselves the same thing. Someone tells Pepper that the missing mask inspires deep introspection and, perhaps, revelation: “You put it on and become something different. You see things differently through it.”
This moment is redolent of another from earlier in the series. In Harlem Shuffle, Freddie tells Carney about the heist of the Hotel Theresa. Once the caper had begun, he’d worn “a rubber Howdy Doody mask” he bought from a discount shop to hide his identity. As the job goes on and dawn creeps on the thieving crew, Freddie gets uneasy: “The eyeholes in the mask made him think something outside his range of vision was about to clobber him.” He’s lost significant perspective. By the end of Cool Machine, Carney and Pepper come to realize that focus on a singular object — in their case crimes and capers, as fun and profitable as they may be — camouflages other insights. In The Colossus of New York, Whitehead’s 2003 collection of essays about the city, he writes that “twilight is a mask factory.” In the twilight of their lives, the Harlemite partners in crime are now more self-critical than ever before. Like a master of three-card monte, a recurring pastime in the trilogy, Whitehead unfolds the trick: Harlem Shuffle laid out the players and the game, Crook Manifesto raised the stakes, and Cool Machine shows Pepper and Carney have focused on the wrong target, conflating money and adventure, the byproducts of their crimes, with the greater rewards of self-knowledge and contemplation.
A major project of Black American literature has been illustrating the richness of Black experiences. Stories of outlaws have been crucial to drawing out the fullness and intricacy of that picture. In the early 20th century, W.E.B. Du Bois’s sociological studies (including The Philadelphia Negro and its investigation into “the Negro problem” and “the Negro Criminal,” the accounts of “badger thieves” and larceny) gave way to the modernism of the Harlem Renaissance, where writers like Zora Neale Hurston, Jean Toomer, Ralph Ellison, Richard Wright, and Chester Himes crafted narratives of Black characters living out of stride with the respectable designs of political leaders. Prominent crime writers of the 1970s, Iceberg Slim and Donald Goines, continued this exploration, as did writers of literary fiction like Toni Morrison, Gayl Jones, and Toni Cade Bambara. Nettie Jones and Walter Mosley turned their attention toward transgressors in the 1980s and 1990s, as did the self-published scriveners of “street lit” and “urban fiction” in the aughts, though less successfully and with diminishing returns. Percival Everett’s Assumption (2011), a crime novel about a cop who isn’t what he seems, also told in three parts, uses instinct and deductive reasoning, the tools of a good gumshoe, to comment on both racial and narrative presumptions. Saidiya Hartman devotes Wayward Lives, Beautiful Experiments, her 2019 book of “critical fabulation” and “close narration,” to the “wayward” Black women of the ghetto at the turn of the 20th century, who reside in places like Philadelphia and New York and challenge doctrinaire attitudes about appropriate ways of living.
The Harlem Trilogy, and Cool Machine in particular, seem like the latest tribute to this kind of off-the-beaten-path selfwork done by people given short shrift in official histories and books that prioritize the fast and forward arrow of upward mobility. Cool Machine, in places, is a detective novel for men on the other side of the law, who check hunches and double back on evidence and places of interest, chasing leads — and running themselves ragged. Instead of wayward, Whitehead’s watchword might be thataway, the phrase used to gesture at wandering thoughts (Harlem Shuffle: “Sometimes he slipped and his mind went thataway”) or the general direction someone has fled in, as in “He went thataway,” the line uttered by a guy Pepper confronts. This term connotes, among other things, the zig-zag method of running to evade bullets or the trajectory of a getaway driver wending through traffic. In another place in Cool Machine, Whitehead uses the expression to mean “somewhere else,” as in, “If you look over here, the city was a gigantic mess, but look thataway and there’s its new face, emerging from the grime. Both things at once, in the same space.”
In place of standardized hardboiled crime fiction, with its emphasis on formula and procedure, Cool Machine is a sophisticated meditation on Black masculinity, aging, and unsanctioned political resistance (Du Bois defines crime as “the open rebellion of an individual against his social environment,” which could apply to revolutionaries or gangsters). Rather than standard thievery, this novel considers another kind of seizure — what it means to lose time, and thus the potential to change, even as everything around you is being constantly reframed. Witnessing their development is the gift of getting to know characters on layaway over nine easy installments. But the insurance afforded by a series can also expose its inherent flaws. As in the first two novels, Carney and Pepper are put through the wringer, but I never felt like they were truly in trouble. The tropes of the crime novel wear thin, with its grim foreshadowing and prodigious exposition. The three-part structure is sometimes predictable, with its movie-of-the-week rhythm, which requires resolution every hundred pages or so. But these are misdemeanors, easy to overlook.
The less obvious thing you have to stare down. This book demands holding at least two truths at the same time: (1) that Carney and Pepper and their cohort are shady dudes, offenders who cause harm to their community, and (2) that they’re also innovators. Like Basquiat, a.k.a. SAMO; the influential Bronx dance-punk band E.S.G.; the early hip-hop musicians; and the unnamed graffiti artists — all mentioned in the novel — these men are alchemists, turning what they had into something else and not just converting goods into cash along the crook’s errant path from hot hand to hock shop. In this book, they use the very crimes that have shaped them, the work they have been handed and clutch late into middle age, to facilitate some new development within themselves.
At one point, Carney walks up 125th Street tuning into the frequency of the neighborhood’s main drag: “Black Israelites waved at passersby. The emissaries from the latest nationalist faction delivered updates on the coming race war, years overdue, as the ghetto blaster at their feet broadcast obscure counter-histories and potluck conspiracies.” Although it’s a novel, I’m beginning to think of Cool Machine as a counterhistory of Harlem’s underworld, one that surprises because it prioritizes human frailty and imagination. Regarding the fate of one mislaid item on the move in this final novel, we learn that there is a crucial two-week period that goes unaccounted for between what happens to the object and the revelation of its fate. The mystery of what exactly occurs in the interim belongs to one character alone — not even the reader knows what went down with real detail, though we can imagine. Here, Whitehead’s joking writing instruction comes in handy. Indeed, what isn’t said is important. In this case, some of the really good stuff happens off the page, in the minds of readers and in the hearts of rogue personalities we can’t quite pin down.
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