How Colson Whitehead pulled off one of fiction’s great crime trilogies

New York City gets the final word in Colson Whitehead’s Harlem trilogy – literally. That’s as it should be, for it’s New York that animates the series more than any single character; the constant but ever-changing playground for his cast of occasional crooks and lovable rogues.Would it be fair, I ask, to call these books an 1100-page love letter to his native New York? “It’s a love letter with a lot of beatings,” Whitehead says. “If the love letter includes beatings, then, sure.”We are meeting on a sunny Wednesday morning at an all-day bistro on the Upper West Side, some 40 blocks south of the main spine of Harlem where Ray Carney, the trilogy’s not-quite-hero, keeps his furniture store.Whitehead has just returned from the Netherlands, where he launched the third and final book in the series, Cool Machine, and is about to embark on a North American tour, with dates scheduled until December. He was also profiled by The New Yorker, a process that required so much time he half-jokingly says he would never do it again.But the 56-year-old is accustomed to the demands of a book launch by now. This is his 10th novel, and today he is arguably the most celebrated living novelist in America; his two Pulitzers for fiction, for The Underground Railroad and The Nickel Boys, made him only the fourth person in more than a century to have won the prestigious prize twice.Whitehead is happy to spend some time on the road marketing his latest ware. “I want the book to do well,” he says. “I’m proud of the trilogy, I’m happy to hustle for it.”Hustlers are at the heart of the Harlem trilogy, which follows Carney, his family and his associates over three decades of criminal escapades in and around the Black epicentre of New York. Every book comprises three novellas, each of which tells a distinct crime caper – typically a heist – that sees Carney pulled further and further into the underworld.Where the first instalment introduced us to an upwardly mobile furniture salesman battling 1960s racial segregation, and the second a middle-aged family man caught in the crosshairs of New York’s 1970s malaise, the final book shows us Ray Carney in his 50s, with both kids out of home, eyeing retirement from both his straight and crooked enterprises.Colson Whitehead and his wife, literary agent Julie Barer.Getty ImagesIt is also the 1980s. Ronald Reagan is in the White House, and the “greed is good” mantra has taken over the city. Modern-day gentrification is taking place, much to our protagonist’s disgust: young urban professionals begin commandeering the crooks’ preferred drinking hole, Donegal’s, and by the story’s end it has been replaced entirely. “The yuppies had won,” Whitehead writes. And ruefully: “There hadn’t been a stabbing in years.”Without giving too much away, it is fair to say the criminal exploits grow more daring and complex as the trilogy goes on. They also expand beyond Harlem, traversing midtown, the gritty Lower East Side and even Queens - and all the class markers therein. Machine’s opening tale centres on an ambitious heist at the grand Waldorf Astoria hotel, where the looters are aided by the homeless denizens of New York’s subway tunnels.“The first two books are very low-technology affairs in terms of the crimes,” Whitehead says. “One of my friends said, ‘No, you have to go big. It’s the ’80s, so go big’.”Carney’s enduring sidekick Pepper, now 64, owns the masterful second portion of the book, as he becomes entwined in a particularly gruesome mission involving a rare and valuable African mask. The perils of crime have taken their toll on Pepper’s ageing body – consigned to “spend more time pissing than thieving these days” – and his suffering only builds sympathy for the old man dragged into one last job.Ultimately, though, we come back to Carney, whose grief and regret over his cousin Freddie haunt him and drive him into a dangerous entanglement in the closing section. This duality runs through the whole series – is Carney fundamentally an honest man with an occasional side hustle? Or is he now more crooked than straight? Did he fall into vice because of its ubiquity, or did he get addicted to the rewards that only thievery can pay?Wisely, Whitehead doesn’t want to weigh in. “The reader can judge for themselves,” he says. “At the opening of this book, his store’s a success, he’s a successful fence [someone who sells stolen goods]. The question is, what is next for him at this stage in his life? What does crime mean? What does being a father mean? What’s the sum of all his choices?”Whitehead is matter-of-fact in his responses and, as in his work, doesn’t indulge in purple prose. He is generous with his time, but we’re not here to chit-chat; he forgoes coffee or food, content to sip table water during our hour together.There are some obvious parallels between Whitehead’s biography and that of his creation, Carney. By the end of the trilogy, the character is the same age as the author is now; both men also have a daughter who has left home. Both are utterly products of New York City.Author Colson Whitehead receives the National Humanities Medal from then US President Joe Biden in 2023.BloombergThat is probably where the similarities end. Whitehead left Manhattan to study at Harvard, and returned to the city to work at The Village Voice newspaper in the ’90s before devoting himself to books and becoming a star. Every writer knows how to hustle, but crime was something he had to study.His research is evident in the book’s rich historical detail – what David Hajdu calls the “rightness” and “evocative precision” of Whitehead’s prose – whether that be sketching 1980s New York or deploying the criminal lingo of the era. For those of us unfamiliar with either, the trilogy is a gateway to further reading: I enjoyed learning about legendary East Village dive bar Downtown Beirut, and I’m certain that being “on the lam” will work its way into my regular vocabulary.It is arguably the funniest instalment in the series, whether in Carney’s depiction of his daughter’s do-gooder white boyfriend (“a nice boy, for a yuppie bastard”), or this account of a character’s new squeeze: “He had introduced her to Club Med vacations and, supposedly, orgasms.”Whitehead says he knew while writing book one, Harlem Shuffle, that he wanted to craft a trilogy. Before it was published, he planned the final scene of book three, and had time to drop details into the manuscript that would set up plot points in the later books. Still, he did not publicly describe it as a trilogy at the time.‘There does seem to be a feeling of optimism in the city. But as a lifelong New Yorker, I always know that the crash is coming. So enjoy it while you can.’“It’s just my personality, I thought, ‘What if I get bored?’” Whitehead says. “I don’t want my obituary to say, ‘He never finished that crime trilogy he talked about in 2019’. I told my friends, but I didn’t tell interviewers.”He did not get bored by it in the end. But seven years is a long time to dedicate to one project. I ask Whitehead whether he received any pushback in the literary world over his commitment to a heist series – the old prejudices against crime fiction. Not in the US, he says, though he detected a little scepticism in Europe. “I think they’re more snobby about that kind of stuff.” Not that Whitehead would care: as he points out, he is the proud author of a zombie novel (2011’s Zone One).There are some subtle echoes of today’s political environment in Cool Machine. Carney fires a sales associate after he admits voting for Reagan twice. Pepper mentions his difficulty keeping track of crises in the Middle East. “They never got solved, they just stacked on top of one another.”How does Whitehead personally parse the social and political times we are in? “The world’s in a pretty terrible place. I hope we survive,” he says. He mentions the destruction of the transatlantic alliance, ignoring climate change, rolling back environmental protections, ICE agents shooting American citizens and mistreating immigrants, and Trump trying to rewrite history by editing history at the Smithsonian – a story that was in the Times that morning.Whitehead sees Trump as both an outlier – a rich celebrity who didn’t have to bend the knee to the Republican Party – and part of the natural cycle of American politics, one that will shift back to the centre. “We never had a left-wing president,” he says. “We’re not a left-wing country, we’re sort of a centrist country.”We move on to the subject of New York, which is in the midst of what might be described as a Hot Girl Summer. It hosted the World Cup, Taylor Swift and Travis Kelce got married at Madison Square Garden, the Knicks are NBA champions for the first time since Nixon. And Mayor Zohran Mamdani is enjoying an extended honeymoon.Colson Whitehead can see himself moving out of New York in the future.Getty Images“People love the mayor, he’s getting things done, he’s much better than our old mayor,” Whitehead says. “There does seem to be a feeling of optimism in the city. But as a lifelong New Yorker, I always know that the crash is coming. So enjoy it while you can.”At 56, Whitehead has lived long enough to witness the boom-bust cycle that underlines the Harlem trilogy and continued thereafter: the 1990s recession, the dotcom boom and crash, September 11, COVID-19. For him, those cycles are an essential part of the city’s nature and charm. Throughout, the vitality of New York as a magnet for artists has never wavered, even if it feels like the endless march of gentrification is making it harder than ever for creatives to eke out a living.“There’s still great, talented people coming to the city, working in the city,” Whitehead says. “They may not be in the West Village or East Village or downtown Brooklyn, [but] they’re in Bay Ridge, or they’re in Bushwick. Some of them are the great-grandchildren of German and Irish immigrants who moved to Harlem, then went to the middle-class and left Harlem, and now 100 years later, their descendants are coming back to Harlem. I love that cyclical nature of the city.”The notion that “the old New York” has been lost – a regular refrain from some jaded city types – is nonsense, Whitehead argues. “If you’re my age and you’re complaining that things aren’t the same, that’s sort of your role as someone who’s getting older. And the fact that you’re not up on what is new and interesting is a testament to its newness and how out of touch you are. And you should be out of touch. I think youth culture is for the kids.”Does Whitehead ever see himself leaving New York? It feels shocking when he says yes, but it shouldn’t be. He and his wife, literary agent Julie Barer, own a home in East Hampton on Long Island, and he envisages basing himself there once his son, now 12, goes to university.“At this point in my life I’m a homebody, I work at home, I make dinner, hang out with my family. I’m not going to the opera every night or availing myself of our plentiful museums and concert venues. I’ve done a lot of time here.”I suggest – somewhat facetiously – that he could write one of those Goodbye to All That essays about leaving New York, a la the great Joan Didion. And I know the answer before he opens his mouth. “I’m a little too cliché wary,” he says. “But that’s definitely a genre.”Before we part, I’m keen to ask Whitehead about artificial intelligence. Earlier this year he penned an opinion piece for The New York Times, decrying the rise of AI and the proliferation of enabling data centres – “gigawatt-sucking, pollution-spewing slop houses of mediocrity”. He was especially cutting about artists who use chatbots in the creative process. “Art is the business of making up stuff,” Whitehead wrote. “Go make up some stuff.”So, does he use AI at all? No, he tells me. Not even a little bit. “I’m not sure what I would use it for.” Indeed, Whitehead is so against AI that he has stopped using Google. If he needs to look something up, he uses DuckDuckGo, a search engine that allows users to turn off its AI component.We share a disdain for having to second-guess whether something was created by a human or by a bot. Whitehead puts it this way: “Does it suck because it’s incompetent or does it suck because it’s AI? That’s the question you have to ask yourself now when you see something that sucks.”This might be the end of Ray Carney’s story, but Whitehead fans can be assured he is already working on his next novel (he told The New Yorker it will centre on the city around the time of World War I).For now, though, he is content to bask in the satisfaction of the trilogy’s completion. “It was a big undertaking,” he says. “I think I stuck the landing.”Cool Machine by Colson Whitehead is published by Fleet ($35).