Colson Whitehead’s Big Score
I was standing at the corner of Ninety-third and Broadway, scanning an empty storefront for signs of literary activity, when Colson Whitehead texted: “Behind you.” It was a clear May afternoon. Whitehead had invited me to his office but specified only the intersection; spinning around, I spotted a dreadlocked figure in shades and a suède jacket, slouched on a bench in the median. Once I’d crossed, he rose to greet me, revealing, on the seat, a plaque that read “Colson Whitehead’s Office.” He cracked a smile. “Got it for my birthday last November,” he said. “No urine or dead animals yet.”
Whitehead, fifty-six, has a reddish-brown complexion, hooded, inquisitive eyes, and a lightly salted mustache-goatee, which, along with his locs, brings to mind mail-order portraits of Black Jesus. He’s long-limbed but unobtrusive in his movements, like a suave giraffe on the lam, an impression reinforced by his tapering brown Chelsea boots. “It’s a weird culture, people who sit on benches,” he said, laughing with a snort for punctuation. A thief in his latest novel uses them for reconnaissance, watching Broadway traffic “until every vector of every possible getaway was a filament in my web.”
Soon, we were riding the elevator to his apartment, in a prewar building near Riverside Park. Whitehead has enjoyed one of the smoothest ascents in contemporary American literature, from his celebrated 1999 début, “The Intuitionist,” a mystery novel about elevator inspectors, to his back-to-back Pulitzers for “The Underground Railroad” (2016) and “The Nickel Boys” (2019). His ten other, wildly disparate books include two satires of media and marketing and an elegiac zombie novel set in Manhattan.
Like New Yorkers fighting over favorite neighborhoods, devoted readers often reproach one another for their ignorance of the real Colson Whitehead. To some, he’s “America’s Storyteller,” as a 2019 Time cover declared, reckoning with slavery and segregation in novels destined to become fixtures of high-school syllabi. To others, he’s a jaded Gen X ironist, who once began a memoir with the words “I have a good poker face because I’m half-dead inside.” And, to still others, he’s the spiritual cartographer of the city that never sleeps, given to such aperçus as that old apartments are “caretakers of your reinventions.” Whitehead himself identifies, improbably, as a slacker. “I’m a really lazy bitch, but I have a punitive superego,” he told me. “The two go together.”
The elevator doors opened, and we stepped through a vestibule into his apartment. On the walls were art works by Kerry James Marshall, Rashid Johnson, and Ellen Gallagher, and books shelved in colorful modular storage units. In the living room, a tabby cat with a clipped ear lounged on a velvet couch, her front paws propping open an illustrated catalogue of military aircraft. “That’s Jupiter,” Whitehead said. “She gets ten per cent nicer every year.” His wife, the literary agent Julie Barer, who’d dedicated his bench, was out, as was their twelve-year-old son, Beckett, who’s been coaching his father through the video game Baldur’s Gate 3. (Whitehead’s other child, Fig, was off finishing a senior thesis at Vassar.) Video games are Whitehead’s usual palate cleanser between projects, but lately he’s been cutting back. “I was going to take a year off from writing, but then, come December, I was really bored,” he said. “Life is short. How many books do I have left?”
His desk was tucked in a corner at the far end of the room, under windows overlooking neighbors’ rooftops. “Should I report that house?” he said, stroking his beard mock officiously as he pointed out a lavish deck. “Some illegal fun you’re having.” The workspace was decorated with framed covers of the Times Book Review, a vintage sign for knife-sharpening services, a taped-to-the-wall headline from Slate (“Colson Whitehead Is Still Just Doing His Weird Thing”), and a poster for “Rififi,” a film noir about a jewel heist.
For the past seven years, Whitehead has been writing a trilogy of New York crime novels. Their protagonist, Ray Carney, is a furniture salesman with a sitcom-worthy family and a sideline as a fence. He’s “only slightly bent when it came to being crooked,” but, in 1959, his cousin draws him into a spectacular robbery. It was meant to be a one-off—as was “Harlem Shuffle” (2021), the novel in which it takes place. Yet both Carney and his creator kept getting sucked back in. “Crook Manifesto” (2023) finds Carney tangling with arsonists amid New York’s seventies decline. “Cool Machine,” out next month, closes out the series in the eighties, as punks, yuppies, graffiti artists, and mafiosi face off in a city “malformed across the centuries—a monstrous entity powered by innate miseries, operated by brute will, and held together by pluck, fury, and rebar.” You can almost see the skyline blush.
“I don’t think there’s a lot of other crime novels where the main character is a real wife guy,” Whitehead observed. He talks about his work as though he were a humble novelty peddler—quite possibly a symptom of impostor syndrome, and a generational horror of coming off like a poseur. But his disavowed intensity finds expression in the monkish professionalism of his characters, whose jobs are at once means of self-avoidance and keys to hidden patterns in the world. More than twenty years ago, he described New York as a city that “multiplies when you’re not looking,” and, in the trilogy, he pursues this idea on a grand scale. The novels are a time-lapse panorama of a metropolis perpetually reshaped by its inhabitants. Whitehead is one of them, and the trilogy is an archeology of his own foundations.
Whitehead was born in 1969, the year that construction began on the World Trade Center’s South Tower. His mother, Mary Ann, came from a prosperous family of New Jersey undertakers, and taught in New York City’s public schools. (One ancestor, William M. Colson, was a merchant who died in Liberia after a feverish bout of correspondence; in the words of an associate, “His love for writing proved fatal.”) Her husband, Arch Whitehead, came from a less privileged background. Born in Harlem, he put himself through Dartmouth by singing in night clubs, and eventually founded a headhunting firm. Gregarious but stormy, he had frustrated literary aspirations, writing poetry and a screenplay entitled “A Werewolf in Harlem.”
Chipp, as Whitehead is known in the family—his full name is Arch Colson Chipp Whitehead—was the third of four children. He arrived after two sisters, Ann and Lynn, and just ten months before a younger brother, Clarke. The family moved constantly, including, once, into the apartment of an upstairs neighbor who’d jumped to his death. “They were still hosing the guy off the sidewalk, and my dad was, like, ‘So, is 11-A available?’ ” Whitehead said. He spent most of his childhood on the Upper West Side and every summer in Sag Harbor, where his mother’s family had a beach house.
“I wouldn’t say nerdy, but he had his hobbies,” Ann said of the young Whitehead, whom she recalls reading comic books and duelling their brother with a toy lightsabre. He and Clarke “were basically the same person until puberty,” Whitehead said, when Clarke emerged as the more “distracted and rascally” of the pair. Lynn told me that Colson shared his father’s moodiness, if not his stifling conservatism. “He kind of stopped in the fifties,” she said. “Not once did I see him in a pair of bluejeans.” He was also prone to fits of rage, especially when he’d been drinking, but he expected stoicism from his children. “Talking about feelings just wasn’t done,” Lynn said. “And we all have a bit of that in us.”
Television was the household’s unifying passion. “Every Saturday on HBO, we’d watch, say, a Sugar Ray Leonard fight or an inappropriate movie like ‘A Clockwork Orange,’ ” Whitehead recalled. “Then, at eleven, George Carlin or Richard Pryor.” Horror was the genre of choice, from George A. Romero’s zombie films to John Carpenter’s “Halloween.” Whitehead fought Clarke for the paperback novelizations of their favorites, and began his study of narrative in the pages of Fangoria.
His ambition was to write for Marvel, or to become “the Black Stephen King.” At Trinity, his illustrious prep school on Broadway, such interests could be isolating, though he eventually fell in with a group of friendly stoners. (In a yearbook photo, he appears in a Joy Division T-shirt under a quote from Joseph Conrad: “We live as we dream, alone.”) Lynn showed him a more expansive New York, turning him on to post-punk and no-wave bands—ESG, Gang of Four, Liquid Liquid—and the Village Voice. “I became this teen-age culture maven,” he told me, regularly going out to see New Wave films or to dance at the legendary downtown club CBGB. In a senior-year English class, he read Gabriel García Márquez’s “One Hundred Years of Solitude” and realized that literary fiction could be as wild as “Carrie” or the X-Men.
In 1987, he went off to Harvard, where he enraged his father by studying English. “ ‘You gotta take economics,’ ” he recalled being told. “I was, like, ‘No, Daddy, I want to sing!’ ” His parents saw him as a future lawyer; instead, he took up smoking and skipped class. Coursework introduced him to Thomas Pynchon, Nathanael West, Samuel Beckett, and Ralph Ellison, all lasting influences. He also improvised his own curriculum of postmodern theory and pop-culture criticism. Whitehead wanted to write, but workshops rejected him and the cliquish undergraduate literary scene put him off. “I’m not really a joiner,” he said. “The idea of auditioning? Screw you.”
Coaxing out his talents fell to a more politic peer. Kevin Young—now The New Yorker’s poetry editor—was a year behind Whitehead, but already a campus prodigy. He’d taken it upon himself to revive a Black student literary magazine, Diaspora, and a co-editor introduced him to Whitehead. “He was wearing a white T-shirt, jeans, and Chuck Taylors, and I was wearing a white T-shirt, khakis, and Chuck Taylors,” Young said of their meeting. “I felt instantly that we were kin.” He published Whitehead’s first short stories, and spent a break living with him in Manhattan, where they saw Afrika Bambaataa d.j.’ing at the Nuyorican Poets Café. Young was fascinated by his ability to find an open diner under any circumstances: “It was like watching a human computer.”
Another classmate was the future director Darren Aronofsky, who cast Whitehead as a zombielike “video junkie” in his senior-thesis film. Whitehead didn’t write a thesis, though a friend who worked for a TV director landed him a gig writing a feature film. “It was a teen sex comedy that was a mix between ‘Risky Business’ and ‘House Party,’ ” he recalled. “The person who hired me, her notes were, like, ‘Can we have a scene where he has to rap his way out of trouble?’ ” After graduation, he spent six months watching television in Sag Harbor, where he, his parents, Lynn, and Clarke—who “drank and drugged his way to getting kicked out of Dartmouth”—were crowded into the same small house. “Basically, it was insane,” he said.
All that television proved useful at the Voice, where he secured a job as an editorial assistant and then, in short order, as a TV columnist. “TV criticism was really frowned upon,” he said. “Only jerk-offs did it.” Still, he threw himself into the role, skewering the “invented New York realness” of gritty police procedurals and the ersatz Harlem of a Bill Cosby-backed series filmed on a Disney studio lot “at the corner of Dopey Drive and Minnie Avenue.” Whitehead also wrote for the Voice Literary Supplement, ridiculing David Foster Wallace’s foray into rap studies, musing about the affinity between cigarettes and spite, and, for a lark, giving a rave review to “Knitting with Dog Hair,” a novelty craft book that he praised as the antidote to “our hyper-cyber times.” His boyishly knowing voice could tip into outright fiction, as with the Prufrockian spin he gave an invented LL Cool J memoir: “I grow old. I grow old. Shall I wear the bottoms of my baggy jeans rolled?”
“The nerve of this kid,” Jeff Salamon, his editor at the Voice, fondly recalled thinking. “Sometimes he’d say, ‘I’m writing about this show,’ and what would come in was basically a fictional character’s experience of the show.” Whitehead was a regular in the smoking lounge of the newspaper’s Cooper Square office, often arriving in a porkpie hat or an “E.T.”-themed beanie. “Everybody was just fucking cool, really on top of it,” he said. “It was before pop-culture criticism broke into the mainstream, and these incredible knights”—Robert Christgau, J. Hoberman, Greg Tate—“were writing about comics and Foucault and Toni Morrison and Run-DMC.” Whitehead started dating a colleague, Natasha Stovall, who wrote about punk music, and they moved in together in Fort Greene.
There were crackheads in the neighborhood, and, once, his landlady’s dog was injured by gunfire. But rent was cheap, and Whitehead had ample time to write fiction between columns. His literary aspirations had solidified on a solo trip through Brazil in the summer of 1994. “I had copies of the Odyssey and Joyce’s ‘Ulysses’ and read them back-to-back, sitting on the beach in my Converse and my cutoff jeans,” he said. “I was, like, ‘O.K., I’m twenty-five. Maybe I should start.’ ”
His first attempt was a satire about a former child actor inspired by Gary Coleman, the star of “Diff’rent Strokes,” imagined as the target of a sinister media company. It was largely an exploration of stereotypes and Black masculinity, Whitehead recalled, and “more theory than story.” An agent was interested, but dropped him when she couldn’t find a publisher. “A lot of people thought I was on a fool’s errand,” he said of his ambitions. “But there’s nothing else that was going to make me whole.”
Vocational commitment was the subject of his début novel, conceived after he spotted a study guide to the elevator-inspector exam at the library. The topic was irresistible: surely no one else had built a mystery around elevator inspection. It also gave him a way to link the rhetoric of Black uplift to the rise of skyscrapers and to millenarian dreams of ascension. His protagonist was Lila Mae Watson, the first Black woman elevator inspector in an unnamed metropolis, who is framed for a catastrophic fall. She belongs to the Intuitionists, a controversial faction of inspectors who communicate with elevators “on a nonmaterial basis.” They await a wondrous “black box” that will bring about the “second elevation,” while their rivals, the Empiricists, scheme to bring them back to earth.
Whitehead drew on Thomas Pynchon, with his infrastructural conspiracies; Ishmael Reed, whose “Mumbo Jumbo” also turns on a racialized metaphysical schism; and Ralph Ellison, with his vision of a marginalized figure illuminating the modern metropolis. “I think my words to him were ‘You’ve written “Invisible Man,” ’ ” Young, who was the first to read it, recalled. He was impressed by the novel’s noirish atmosphere, its deadpan approach to the fantastical conceit, and its wit, which stopped short of cynicism. “All his books have a layer of irony, but that’s to get you there at the table,” Young explained. “He’s always feeding you more.”
Whitehead recalled his father’s gruff skepticism: “How many elevator inspectors are there in the world? Who’s gonna buy it?” Yet the novel found a publisher quickly. A friend encouraged him to send it to Nicole Aragi, a young agent who also represented Junot Díaz, and she placed it at Doubleday. (He’s remained with both agent and publisher ever since.) In 1997, Stovall had persuaded Whitehead to move to San Francisco, where he found a dot-com-boom job writing copy for CNET. But California didn’t agree with him, and they moved back to Fort Greene just before the novel appeared. It was so successful that Whitehead had to improvise an extended book tour. Back in San Francisco, he said, “the only friend I had left was a dominatrix, so I slept in her dungeon.”
“The Intuitionist” arrived amid a new critical appetite for so-called literary genre fiction. That same year, Doubleday published Jonathan Lethem’s “Motherless Brooklyn,” another mystery novel whose deeper subject was the soul of urban life. “What binds us together is that we both remember specific, sacred, weird details about New York in the seventies and eighties,” Lethem said of Whitehead. “Sometimes I feel like our books are messages to each other.” The two were often paired at readings and became fast friends, frequently seeing each other at a poker night of Brooklyn writers that also included Nathan Englander and Heidi Julavits. Whitehead’s cool, exacting voice reminded Lethem of Rod Serling hosting “The Twilight Zone”: “The real Colson is there but standing to one side.”
His second novel was as encyclopedic and freewheeling as his first had been enigmatic. “John Henry Days” (2001) was inspired by the myth of the Black railroad worker who’d died after beating a steam drill in a race. The folk hero makes a few elliptical appearances, along with the bluesmen, scholars, and Tin Pan Alley tunesmiths who shaped his legend. But the main action takes place at a John Henry festival in mid-nineties West Virginia, where J. Sutter, a hack journalist who lives in Fort Greene, has been sent by a content-hungry website. Sutter is trying to break his friends’ record for consecutively attended publicity events, the idea being that he, too, is locked in a death match with technology. The novel sprawls, sometimes awkwardly, but its media satire is mordantly hilarious, and it cemented Whitehead’s wunderkind status. In 2002, he received a MacArthur Fellowship, a windfall that prompted him and Stovall, who had married at the turn of the millennium, to start trying for a baby.
Not everyone was taken with his cleverness. Infamously, the novelist Richard Ford spat on Whitehead at a party, as payback for a pan in the Times Book Review. (Whitehead had mocked the older writer’s adulterers as less sinful than whiny.) Whitehead himself was panned by James Wood in The New Republic, who described “John Henry Days” as “full of noise and irrelevant intensity” and corrupted by “the mad fluency . . . of email.” Eight years later, Whitehead answered him in Harper’s, parodying the critic’s fastidiousness in an essay that declared “He lifted the cup” a perfect sentence: “Aha! cries the famished reader. This is minimalism at its well-marbled finest.” But Wood had also charged Whitehead with avoiding introspection, echoing an assessment that the novelist—who’d developed a self-protective reserve in childhood—was also beginning to reach. Whitehead had been toying with a fabulist reimagining of the Underground Railroad but decided that he wasn’t yet mature enough to do it justice. Before he could write about slavery, he would have to risk something of himself.
Later in May, I met Whitehead in East Hampton, where he and Barer have a house. It has two white cubical wings connected by a sky bridge, where I could see his silhouetted figure setting the table for lunch. “It’s not officially a gumbo, because there’s okra, tomatoes, and no roux,” Whitehead explained upstairs, tying back his locs to stir a pot of piquant-smelling stew. A passionate cook, he makes most of his family’s meals, specializing in smoked ribs, pork vindaloo, and fried chicken of every nationality, a dish to which he once devoted an essay. Grilling was his father’s métier, and a highlight of their summers in Sag Harbor, though Arch approached it more austerely. “He literally only made chicken,” Whitehead said, and took offense at requests for barbecue sauce.
A Pavement song played as he dished out two servings, apologizing for an excess of salt I struggled to detect. He seemed more guarded than before, and I changed the subject from his father to his son. “I thought if we named him after someone depressive and serious, he might become a happy-go-lucky jock or a stockbroker,” Whitehead said. Yet Beckett seems to be taking after his father, immersed, as Whitehead once was, in the worlds of “Star Wars” and D. & D. He’s also a military-history buff, and this summer the family will celebrate his bar mitzvah with a trip to see the D Day beaches in Normandy. “We’re going to rent a shuttle bus,” Whitehead said, “and I picture it as a sort of ‘Little Miss Sunshine’-type thing, where everyone has an arc over the course of five days.”
For now, there was another fraught beach to revisit. After lunch, we set out for Sag Harbor in Whitehead’s black BMW X5, which he carefully piloted, hands at ten and two, down empty roads half hidden by scrubby Long Island pines. (He earned his driver’s license during the pandemic, in a Zoom class where all the other students were teens.) There was little to see until we reached Azurest, one of three historically Black enclaves on Sag Harbor’s outskirts. Whitehead took a right at a sign depicting a dozing fisherman, continuing up a shady road toward the bay.
Sag Harbor, an old whaling port, was once known as the “Unhampton,” for its relative quaintness. In the nineteen-forties, it became one of the first towns in the area where Black families could acquire beachfront property. Whitehead’s maternal grandfather, T. Colson Woody, bought in early, and generations of his family have vacationed there since. Mary Ann came there as a girl, then with her schoolteacher friends on summer breaks, and then with her husband and children, who played with her friends’ children on the beach or in the woods between developments. “Chipp and Clarke and their gang of boys would build forts on the beach and shoot off bottle rockets,” Lynn recalled. “We had free rein.”
Whitehead wrote his 2009 novel, “Sag Harbor,” to memorialize those bygone days, largely erased by the area’s “Hamptonization.” Its colorful mid-century houses have increasingly given way to metal-roofed McMansions and, with them, a much whiter population. Seven years ago, a group of Black families had the old developments inscribed on the National Register of Historic Places, hoping to hold back the tide. By contrast, Whitehead was fatalistic. “That’s just the way of things, the ebb and flow of populations,” he said. “I love this place, and, also, I don’t have to live here.” In East Hampton—which his teen protagonist envisions as a land of “pterodactyls wearing ascots”—there’s more privacy, he said, and fewer of the “ghosts and toxic emanations” that he wrote “Sag Harbor” to exorcise.
It was a novel he wasn’t ready to write until he was almost forty. After “John Henry Days,” he began another satire, “Apex Hides the Hurt,” about a “nomenclature consultant” tasked with renaming a small town out West. Yet he felt unable to continue after the Twin Towers fell on 9/11, which he watched from Fort Greene Park. Like millions of New Yorkers, he felt that something had been torn not just from the skyline but from his psyche. “I thought they’d always be there standing over me,” he recalled telling his therapist, who brought him to tears by responding, “Like your parents?”
He pivoted to a book of essays, drawing its title, “The Colossus of New York” (2003), from one of the sci-fi monsters of his childhood movie nights. They’re playful, intimate sketches, each sentence an errant transmission from the city’s collective consciousness. In the essay “Port Authority,” Whitehead eavesdrops on the dreams of eager new arrivals; in “Morning,” on the unspoken indignities of the daily commute. “You are a New Yorker when what was there is more real and solid than what is here now,” he writes in the introduction. Later, he adds, “New York City does not hold our former selves against us. Perhaps we can extend the same courtesy.”
The slim volume marked the beginning of a transformation, though several years passed before it ramified. In 2004, Fig was born, and Whitehead took the first of several teaching jobs to provide for his family. He struggled to finish “Apex,” which appeared in 2006 to a lukewarm reception. Tired of being a remote puppet master, he began to consider the traditional novel of origins his younger self had eschewed.
We pulled up to a cherry-red bungalow on an exposed cinder-block foundation, with a deck overlooking the bay’s placid expanse. It was the house of Whitehead’s adolescent summers. He climbed its peeling steps to the deck and stared at the water, his back to the door. “Do you want to go inside?” he asked a minute later, with a resigned, knowing look. I felt like one of the hacks from “John Henry Days.” (But of course I said yes.)
Dated brown couches huddled in musty silence. A slender kitchen island, once his father’s liquor cabinet, stood near a refrigerator laden with sun-bleached photo magnets. No one has lived there since Mary Ann died, three years ago; in 1990, she and Arch left New York and moved in full time—for her, the beginning of a glorious retirement, for him, the acknowledgment of a professional setback. His firm had never recovered from the Wall Street crash of 1987, and his heavy drinking continued.
“His anger was a ruling force in my life for so many years,” Whitehead told me, recalling “volcanic” fights over everything from his writing career to the profanity in Prince’s “Sexy M.F.,” which Whitehead dared to play at Christmas. “One day, he was unloading on me, and I was, like, ‘I’m thirty-two. I don’t live here anymore.’ I just walked out.” They stopped speaking.
We walked a few blocks inland to the family’s other house, a stolid white saltbox built by Mary Ann’s father in the nineteen-forties. In the mid-two-thousands, Whitehead periodically rented the house from an aunt, hosting friends on nostalgic trips that spurred him to write about the place. “It used to be much more secluded,” he said en route, as we stepped aside for contractors’ trucks and vans. Once there, he led us to the back yard, pointing at a trio of windows above a porch mottled with lichens. It was the bedroom where he and Clarke had stayed in as boys. “He had his blue bike, and I had my yellow one,” he said. “We’d set off in the mornings and not come back till the lights came on.”
Their childhood’s twilight is at the core of “Sag Harbor,” which he wrote at the house in 2008. On the surface, it’s a Gen X coming-of-age comedy, satirizing the postpubescent neuroses of “black boys with beach houses” in the street-obsessed eighties. Benji, the protagonist, who narrates from adulthood, is fifteen and determined to distinguish himself from the brother who’s always been his double. He roams the developments with a group of boys whose priorities include girls, cars, BB-gun fights, and mastering the “assorted field exercises of black boot camp.” (“Everybody was faking it,” Benji triumphantly concludes after watching two friends fumble a handshake at the beach.) Yet the book is also about the disappearance of time and places, with summer’s end presaging more permanent losses. “Ask, How long are you out for? and a cloud wiped the sun,” Whitehead writes. “The question trailed a whiff of autumn.”
Another cloud is adult dysfunction. Benji’s father is a volatile patriarch who grills during blizzards and hits him for failing to manfully respond to a classmate’s racist slight. The father is occasionally charming, even tender, but also an alcoholic, whose afternoon cocktails portend such upheaval that Benji learns to play dead when he hears the click of the kitchen island’s magnetic lock. When the novel was published, in 2009, Whitehead called it semi-autobiographical. Seventeen years later, he didn’t mind admitting that he’d changed little other than the names.
Arch died less than two months before the book’s publication. He’d spent a bucket-list year writing in Ecuador, then returned to enter hospice, sick with a cancer that he’d hidden from his children. “I didn’t want to be the jerk who didn’t talk to their dying dad,” Whitehead said, but when he visited his father he was angrily rebuffed. “He said, ‘It’s too late to apologize,’ and I said, ‘I’m not here to apologize. I just wanted to say goodbye.’ ” Mary Ann signed off on the novel, and Clarke—who, after a series of odd jobs, had just earned a master’s in teaching—was touched by how much his brother had remembered. “For me, that book was ‘I’m gonna let it all hang out, and it’ll be good for me as a writer and as a person,’ ” Whitehead said, adding that he probably couldn’t have written it if he and his father hadn’t been estranged. “It was part of becoming a grownup.”
He was relieved to have written a character so like himself without readers “recoiling in terror.” But one person had reacted differently than he’d hoped. For years, he and Stovall had been divided over their future. They split up a few months after “Sag Harbor” was published, and though neither was anxious to discuss the circumstances, an aside in Whitehead’s fried-chicken essay hints at the final straw. “I sent Sag Harbor to someone who’d read a lot of my previous work, and she was taking her time getting back to me,” he writes. The reticent reader turns out to be his wife, who, when confronted, admits that she prefers the protagonists of his other books. “ ‘You know the main character is basically me, right?’ ” he asks her. Then, en route to a reflection on collard greens, he adds, “We’ve gone our separate ways.”
We ended the afternoon with a walk to Sag Harbor’s downtown, a stretch of restaurants and boutiques which terminates in a long wharf. There was the ice-cream shop where he’d worked as a teen, and the century-old grocery store that inspired a novel by John Steinbeck. Whitehead sat down on a bench in front of the Five and Dime, a general store with a red-and-yellow awning. He draped his arm over the backrest and stretched out his legs, looking relieved to have cleared the day’s gantlet. “There’s a lump on my back, and I thought, Maybe it’s my last interview. Do I have any famous words to impart?” he’d said on the walk. “But then I went to the doctor, and he was, like, ‘It’s just a lump of fat.’ ”
Whitehead’s family would be joining him the next day in East Hampton, and he was awaiting an Uber when a man in a hat and shades introduced himself as a photographer. “I’m doing a project on the famous authors of Long Island,” the man said, scribbling down his number. “Maybe we can take some frames?”
Five hundred people had signed up to see Whitehead speak at the Teton County Library, in Jackson Hole, Wyoming, and a few dozen had gathered backstage in its auditorium for a reception.
“Two Nobel Prizes!” an elderly woman exclaimed, clasping the author’s hand in hers. She evidently meant his Pulitzers, but he smiled gamely, telling her that he was “working on the peace one.”
“Congratulations on your literary successes!” another woman said.
“Thanks!” he replied. “I have no hobbies.”
He floated among the tiny tables, nursing a lime LaCroix and picking at finger foods. Some fans wanted to tell him where they’d once lived in New York City. Others expressed surprise that the author of such harrowing novels seemed to radiate inner calm. The vast majority were older white women. (So was the reader who, a week earlier, had seen me on the subway with a copy of “The Nickel Boys,” and demanded to know why I wasn’t in tears.)
Whitehead took the stage at around seven, rocking at the hips like a boxer readying himself to deliver a quick knockout. “Howdy-do,” he began, to immediate laughter, then embarked on a mock recitation of his life story. “I was born a poor Black child,” he said. “I remember the days sittin’ on the porch with my family, singin’ and a-dancin’ down in Mississippi. Or maybe that was someone else. Steve Martin in ‘The Jerk.’ ”
He continued in that spirit for the next forty minutes. Whitehead has long cultivated a faux-naïve persona in book talks and opinion pieces. At one point, he brought up the Gooch, an A.I. assistant he’d invented for an essay in the Times—who pings him, he claimed, whenever he loses his butt. He might have made a good comedian, and he briefly considered writing a novel about Richard Pryor, whose portrait he keeps behind his desk. But humor also helps him evade the projections people make about his work. Whitehead has been labelled a “genre bender,” an embodiment of Obama-era “post-Blackness,” and an emissary of “literary Brooklyn.” He has deftly escaped these pigeonholes, in part by insuring that each of his books is radically different from the last. That got harder when he won American literature’s most prestigious awards for back-to-back novels about slavery and segregation.
Afterward, he was asked about race and politics almost exclusively, a narrowing of his work that often chafed. Onstage, he preëmpted such expectations with a joke. “ ‘I thought you said they were bringing that slavery guy,’ ” he said, pretending to be a member of the audience. “ ‘He’s up there talking about Gary Coleman and Neanderthals!’ ”
Whitehead always knew he’d eventually write a “slavery book,” he’d told me earlier. “Everyone does.” But he postponed his for many years. During his divorce, he wrote “Zone One” (2011), a novel that is set in the shaky aftermath of a zombie apocalypse and follows a crew of bored, traumatized “sweepers” as they purge Manhattan of the remaining undead. Next was “The Noble Hustle” (2014), a comically abject memoir about competing in the World Series of Poker. In 2013, he was about to embark on a novel about a Brooklyn writer’s midlife crisis when he told Barer, then his fiancée, about an idea he’d had for a literalized Underground Railroad.
Kevin Young had introduced the pair in 2009, at a tenth-anniversary conference for the Portland literary magazine Tin House. Two years later, they crossed paths again when a mutual friend’s change of plans left them alone together at drinks. “It was clear that he was interested,” Barer told me. They bonded over growing up between the Upper West Side and Long Island. Whitehead was also struck by Barer’s seriousness about her work as an agent—commitment to one’s calling being the signature quality of his protagonists. The trait was on display when he mentioned his idea. “I was, like, ‘Please drop everything and write that book!’ ” she said. By the end of the year, they were married, Beckett was born, and Whitehead was writing “The Underground Railroad.”
The joy of new marriage and renewed fatherhood helped him through the darkest story he’d ever told. Cora, the novel’s heroine, is a slave on a Georgia plantation, where she’s stigmatized because her mother escaped when she was a child. After her master dies, she, too, runs away, and the heretofore realist narrative takes a speculative turn. She travels via subterranean tunnels and train stations to the Carolinas, Tennessee, and Indiana. Each state evokes a different phase of white supremacy and the unending battle against it, folding events as disparate as the Tuskegee syphilis experiment and the Exoduster movement into a panoramic allegory patterned on “Gulliver’s Travels.”
The prose had more fleetness and gravity than anything he’d previously written, while the structure conveyed the ironies of history without the showy encyclopedism that had bogged down “John Henry Days.” In one scene, Cora is hired to reënact her enslavement at a living museum. “Old Colson would have been, like, ‘Who’s the curator? What’s the theory?’ ” he said. “But I no longer had the need to catalogue so thoroughly.” The novel’s success was seismic. Oprah selected it for her book club; at her compound in Montecito, Whitehead was so nervous that her staff insisted on blow-drying the damp patches of his dress shirt before they were introduced. A few months later, he won the National Book Award for Fiction. The ceremony was just eight days after Trump’s election, which, uncharacteristically, moved Whitehead to issue a rallying cry from the lectern: “Be kind to everybody, make art, and fight the power.”
Whitehead has never avoided politics; he joined Zohran Mamdani’s inaugural committee, and he has weighed in on everything from the way A.I. threatens human creativity to the mistreatment of pro-Palestine activists. Yet he’d always kept political agendas from determining the course of his imagination. Even so, America’s latest white-supremacist turn propelled him toward another dark history: the discovery of a mass grave on the grounds of a shuttered Florida reformatory called the Dozier School for Boys. Surviving former residents alleged that rape and torture had been routine there for decades, especially under segregation, when Black boys bore the worst of the abuse.
“The Nickel Boys” fictionalizes their unspeakable experiences. As in “Sag Harbor,” Whitehead’s subject is a community of adolescent boys, a pair of whom illustrate divergent paths—not, this time, out of paradise but through an inferno. Elwood is a promising, almost unbelievably innocent young man whose pastimes include reading the encyclopedia and listening to Dr. Martin Luther King, Jr., on vinyl. He aspires to join the civil-rights movement. Then, after hitching a ride from a stranger in a stolen car, he’s sent to Nickel Academy, where he befriends Turner, a boy of similar age whose misfortunes have left him more worldly-wise. Their entwined struggles pose questions about the utility of righteousness in a system of inhuman cruelty, which come to a head, years later, in a dramatic reversal.
Both “The Underground Railroad” and “The Nickel Boys” inspired screen adaptations, by Barry Jenkins and RaMell Ross, respectively. Jenkins had been pursuing Whitehead since he first read “The Intuitionist,” in 2010. “I was, like, ‘A Black woman is basically Luke Skywalker?’ ” he told me. “ ‘Sign me up.’ ” Years later, the success of “Moonlight” emboldened him to try for “The Underground Railroad,” and this time he managed to earn the author’s trust. Jenkins lavished attention on the cinematography of his series, which came out in 2021: “We created an entire lighting scheme around the way he described the Great Spirit.” Ross’s film, which came out last year, was shot from the boys’ points of view in colorful hues that belie their situation’s brutality. Whitehead, who’d praised Jenkins’s adaptation at the podium in Wyoming, was evasive when asked about Ross’s. “For me, ‘The Nickel Boys’ is a story of psychological realism, and the adaptation was a little ethereal,” he said. A woman in my row turned to her companion and hazarded a translation: “He hates it!”
Obscured by the film’s unusual perspective is the novel’s third-person remove, which gives space to the question of why one boy makes it out alive and the other doesn’t. Midway through writing “The Nickel Boys,” Whitehead lost his brother, Clarke, who was only forty-eight. Like Arch, Clarke had become an alcoholic, and was unable to shake his addiction even after he found a stable career in teaching. In the years before his death, he was in and out of rehab, relapsing despite his siblings’ efforts to keep him sober.
“Around Thanksgiving in 2017, his landlord called and said, ‘Your brother’s dead,’ ” Whitehead had told me. “I was in shock.”
It fell to Whitehead to enter Clarke’s apartment, above a pizza parlor in Bay Ridge. Since “Sag Harbor,” he had been processing their drift apart through his fiction, and he had already begun to give something of their bond to Elwood and Turner. But, once the medical examiners had left and the necessary calls had been made, Whitehead, alone in his brother’s bedroom, could see that Clarke had never really left their tandem youth. “We did everything together,” he told me, laughing softly as his eyes welled. “And he still had all of our childhood totems, like the poster for ‘Escape from New York.’ He never outgrew them.”
Light filled the uptown 1 train as it climbed onto the elevated tracks. “They were green in the seventies,” Whitehead said of the seats, unlike the orange and yellow of today’s car, itself soon to be retired. As children, he and Clarke liked to press their noses to the windows and look down the tunnels: “Soot would powder us.” In the nineties, he remembered late-night trains where everyone—including him—would smoke, until a police officer put an end to the “cocktail party.” Best of all, he said, was finding himself in a car that was completely empty, as though headed for “some weird ghost-map alternative universe.”
From theoretical elevators to abolitionist undergrounds, Whitehead has always drawn metaphors from the mysterious mechanics of transport. The subway is his urtext, and a key inspiration for his trilogy was the 1974 heist film “The Taking of Pelham One Two Three.” Four men hijack a subway and demand a million-dollar ransom, setting off a chain of events that touches every stratum of city life. Passengers swear and cry in multiple languages; at Gracie Mansion, an unpopular mayor hesitates to address the public for fear of being booed. “Everybody is just, like, an angry New Yorker,” Whitehead said. “They’re sweating and bickering in great outer-borough accents, and there’s a schlumpy existentialism, too.”
His trilogy is, likewise, a straphangers’ gallery of metropolitan oddballs, from Zippo, a pyromaniac turned blaxploitation filmmaker, to Uncle Rich, a master criminal who stages a daring raid on the Waldorf-Astoria from a disused train tunnel with the help of a homeless army. Like “Pelham,” the novels map New York through the endlessly ramifying consequences of crime, which illuminate its workings like radioactive tracers in a monster’s bloodstream. At its heart is one relentless imperative—to rise.
From the 1 stop at 137th, we made our way to Strivers’ Row, a stretch of limestone- and terra-cotta-fronted town houses known since the Harlem Renaissance as the most elegant block in the area. Whitehead remembered attending a Jack-and-Jill event in one of the houses: “Considering how run-down the rest of the neighborhood was in the seventies, it was really stark the way they glowed.” In the trilogy, Ray Carney and his wife, Elizabeth, raise their two children on the block, just steps from her own childhood home. “After what I put Cora and the Nickel boys through, having someone who could scheme and win and not be totally defeated by racism and capitalism was intoxicating,” Whitehead explained. Yet Carney’s journey is fraught with Odyssean dangers, which he faces with uxorious determination: “What else was an ongoing criminal enterprise complicated by periodic violence for, but to make your wife happy?”
Carney is not only a clean-cut and charismatic salesman—“If that sofa you’re resting on is familiar, Mrs. Williams, that’s because it was on ‘The Donna Reed Show’ ”—but the son of a violent criminal. His spectre haunts Carney, particularly because his father’s ill-gotten gains were his store’s seed capital. His sideline as a fence compounds this unsteady compartmentalization; a bridge between legitimate and illegitimate worlds, he sees his job as facilitating “churn,” or the “natural flow of goods in and out and through people’s lives.” At the start, he limits himself to helping Black thieves in Harlem sell stolen electronics to the merchants of Radio Row, in the Financial District. But his wayward cousin Freddie constantly inveigles him into more serious mischief. At the end of “Harlem Shuffle,” Freddie aids the junkie scion of a corrupt Manhattan Dutch real-estate dynasty in pilfering the family safe, forcing Carney to deal with the aftermath.
The caper unfolds amid the Harlem riot of 1964, dramatizing the differential treatment of impoverished looters and the bigwigs who “notarized their misdeeds or engraved them into bronze plates for building façades.” Its climax is a thrilling chase through midtown; skilled at wringing texture from tension, Whitehead makes every close shave an excuse to animate the city, at one point inventing an entire Broadway show—critical reception included—in the time it takes Carney to sprint through its exiting audience. But the novel’s spiritual conclusion is the demolition of Radio Row to clear the way for the World Trade Center. “The buildings of the old city loomed over the broken spot, this wound in itself,” Whitehead writes. “If you bottled the rage and hope and fury of all the people of Harlem and made it into a bomb, the results would look something like this.” The passage echoes Whitehead’s response to 9/11, as Carney mourns the neighborhood that the Twin Towers would supplant.
Earlier, we’d cut across St. Nicholas Park, with its steep stone stairs and outcroppings of exposed bedrock. “Atop the unchanging schist, the people replaced each other, the ethnic tribes from all over trading places in the tenements and townhouses,” Whitehead writes in the second installment, “Crook Manifesto.” It’s the nineteen-seventies. New York is bankrupt and Harlem is aflame, as slumlords torch buildings for insurance money in cahoots with politicians pushing “urban renewal.” Paralleling this fiery drama is a slower accretion of changes to the city’s fabric, which convey an almost tectonic sense of time’s passage. For research, Whitehead trawled the front pages of every New York Times from the period, read mayors’ memoirs and the autobiography of a mobster’s widow, and watched strangers’ digitized 8-mm. footage on YouTube. “Were they wearing hats?” he said. “How much was a tongue sandwich? For me, that’s gold.” Realism and fantasy go hand in hand, he told me: “Being precise allows you to make things up.”
We passed the Harlem Y.M.C.A. at 135th and Seventh—across the street from its original site, where Langston Hughes once lived. (Whitehead’s next novel, which centers on New Yorkers before, during, and after the First World War, features a character who stays there, though Whitehead declined to say more about the book: “Right now, it’s just mine.”) The trilogy also follows in a long tradition of Harlem fiction, including Chester Himes’s detective novels and the more recent mysteries of Walter Mosley. But they’re even more indebted to Donald E. Westlake, whose Parker novels, under the pseudonym Richard Stark, persuaded Whitehead to write about criminals rather than detectives.
“If Elmore Leonard had been alive, he would’ve fucking loved them,” Graham Yost, the showrunner of an FX series based on a Leonard novella, said of Whitehead’s trilogy. He’s working on a “Harlem Shuffle” adaptation for Apple TV, to be produced by Barry Jenkins, and praised Whitehead’s decision to focus on a small-time criminal. (At one point, Carney struggles to hold a gun.) The pilot will dramatize the trilogy’s opening heist at the Hotel Theresa on 125th, a thirteen-story tower with a striking white façade once known as the Waldorf of Harlem.
“It was really glamorous seventy years ago,” Whitehead said when we reached the building, now an office complex with a White Castle on the ground floor. A neighborhood history marker detailed its glorious past, under the ominous heading “While We Are Still Here.” The eternal question of who belongs in New York comes to the fore in “Cool Machine,” as the slicker but no less corrupt city of the eighties rises from the ashes of burned tenements. The book’s relatively gentrified heists involve the art market, the profitable advent of cable television, and various criminals’ suburban retirement plans—underscored by repeated allusions to John Carpenter’s dystopian thriller “Escape from New York.” The movie’s eye-patched protagonist, Snake, lands a glider atop the World Trade Center, tasked with rescuing a kidnapped President from a city that has descended into anarchy.
Not everyone can “make it here,” at least not forever. The book’s second novella—each installment of the trilogy comprises three—is told from the perspective of Carney’s accomplice Pepper, a stoical enforcer and friend of his father’s of whom we had been told, “Any smile that broke out on his face was a mutiny swiftly put down.” A brooding sideman in the first two books, Pepper emerges as the most sympathetic character of the third, aging in a city he no longer recognizes. He swigs Pepto-Bismol for relief from what might be stomach cancer. Yuppies have taken over his favorite bar. On the hunt for a stolen African mask, he falls in with a young restitution activist whose arty downtown world seems to him like a foreign country. “What the hell was a Liquid Liquid?” he wonders after a punk concert. “Sounded like the complaint of an angry janitor.” It’s the New York of Whitehead’s CBGB youth, seen through the eyes of a relic from the days of street preachers and dream books.
At last, we reached the northeast corner of 125th and Morningside, where a streetwear store occupied the ground floor of a four-story apartment building. “So here we are,” Whitehead said grandly—Carney’s Furniture, his hero’s hard-won slice of the city. Last year, after a “Harlem Shuffle” walking tour, he happened to pass by the shop with extra copies. “I was, like, ‘Here, I wrote about this address in my crime book,’ ” he said, doing jazz hands and affecting a needy-author voice. At the register, two “twentysomething dudes on their phones” gave him blank, pitying stares. “They were a little wary, like, ‘Is this a religious pamphlet?’ ” He laughed-snorted at the memory. Then he rounded the corner to the building’s other side, where a door’s outline was faintly visible under thick red paint. It was Carney’s side entrance and portal to the underworld, whose inexorable gravity is described as a “sickness drawing everything into itself.”
At least in their professionalism, Whitehead’s protagonists have always had an element of self-portraiture. But in Ray Carney—a man whose relentless striving brings him only closer to the past—he’s invented an unusually perfect double. What’s a novel but a big score of details burgled from the world? And what’s a novelist but a fence, furnishing imaginary scenes with choice pieces of reality while obscuring their provenance? Over the years, it becomes clear that he does what he does not just for the money, or even for the thrill, but because it makes him part of the churn, a safe for the secrets of a city so quick to change that, as Whitehead writes in “Colossus,” “we can never make proper goodbyes.”
Near the end of the trilogy, Carney and Elizabeth dine at Windows on the World, the luxury restaurant that once looked out from the North Tower’s uppermost floors. It’s another reference to “Escape from New York,” which Whitehead watches annually in honor of Clarke: “If I don’t do it, who will?” ♦