There’s Colson Whitehead up ahead, minutes before our arranged time, dawdling on the corner of 126th Street and Fifth Avenue, dressed in slim jeans and Chelsea boots, his dreadlocks cutting a clean line across his back. I’m content to nurse a half-block distance between us and observe. Whitehead’s walk, by the way, is not what the youngsters would call swaggerific. Swagger is imitative, and the way Whitehead moves evokes less a simulacrum of a strut than it does acceptance of his stature and physiology, most notably that he’s long and lean and a little knock-kneed. He stops on 127th Street, and since I’m a few paces behind him and don’t want him to glance back and peep me trailing, I call his name. He snatches wired headphones out of his ears and reaches out for a handshake — our first. “Nice to meet you,” I say. “I think we’re headed in the same direction.” He smiles, and the sun hits the blue of his glasses. “Yes, I think so,” he says, and in tandem, we mosey the half block it takes to reach our destination: the Langston Hughes House.

Whitehead is on his way to a landmark place in African-American history in more ways than one. Three years ago, he published a novel, The Underground Railroad, that shot him to literary stardom. With it, he became only the second writer of color and sixth writer ever to win both a National Book Award and a Pulitzer Prize for the same novel. The book, which imagines an actual railroad for the transportation of enslaved people in search of freedom, was also an Oprah’s Book Club selection, sold over a million copies and earned the praise of President Obama. Barry Jenkins, the Oscar-winning director of Moonlight and If Beale Street Could Talk, is adapting it into a limited series.

Where do you go after that? For Whitehead, it’s the era of Jim Crow. His next novel, The Nickel Boys, out July 16, follows two boys struggling through their sentences at an abusive reform school under the specter of segregation in the 1960s. It’s a book that will further cement his place in the pantheon of influential American writers.

He has written seven books of fiction and two books of nonfiction over a 20-year career. And even before The Underground Railroad, he had earned accolades and become a best seller. Explorations of race and history have been a through line from his early works — his first and second novels, The Intuitionist and John Henry Days — to the present. But Whitehead is unwilling to be boxed in by any school of thinking, any mode of creating. He has also written satire (Apex Hides the Hurt), zombie horror (Zone One) and a hilarious nonfiction book on poker (The Noble Hustle). George Saunders, an acclaimed contemporary, writes to TIME: “He is a splendidly talented writer, with more range than any other American novelist currently working — he can be funny, lyrical, satirical, earnest — whatever is needed by the work.”

Though it’s dialed up or down in each book, I read a constant thread of humor in his work, that he’s having a damn fine time creating it and, furthermore, that he’s in command of both his subject and the conventions of any given genre, which allows him to transform them.

Whitehead’s two most recent novels stand apart in that they most directly satisfy a mandate set out by W.E.B. Du Bois, co-founder of the NAACP, for black writers to create work in service of justice. Books about the past have always helped us understand our present; Whitehead’s in particular feel crucial to understanding our current cultural and social climate. In a moment when Senate majority leader Mitch McConnell has made headlines for discrediting the need for slavery reparations and former Vice President and current presidential candidate Joe Biden is under fire for excusing his past work with segregationists, Whitehead’s books are a vital reminder that American racism is far from bygone. “I had never read anything with an enslaved person as a main character where I really felt that sense of dread, claustrophobia and the narrowing of choices,” recalls two-time National Book Award winner Jesmyn Ward, who served on the jury the year The Underground Railroad won. “I felt the book could be a breakthrough experience for some people.”

As we approach the home of one of the most famous black writers ever, I tell Whitehead that it now houses the I, Too, Arts Collective, a nonprofit dedicated to nurturing voices from underrepresented communities in the arts — one I’ve worked with as an author. The program director greets us at the door. She offers us a tour of the home that today smells of the polish used to buff the dark wood floors to high gloss. Whitehead obliges, but not before hanging his coat in the hallway (“I didn’t want to disrespect Langston’s house,” he’ll say later), and follows her through the old brownstone. She walks us past a front room adorned with a grand piano and Hughes’ typewriter perched on the ledge above a fireplace. Whitehead asks questions, idles for a moment in each room, taking it in. He seems to reflect on the importance of Hughes’ legacy, of him moving through the space of a writer who made space for him.

One of Hughes’ most famous poems is “Harlem” — named for this neighborhood that birthed African-American literature’s most storied renaissance. The poem begins with the verse: “What happens to a dream deferred?/ Does it dry up/ like a raisin in the sun?” Hughes was referencing the dreams of African Americans in Jim Crow America, but his question could also be asked of an author’s dreams. The most grand of those feature critical acclaim, awards, strong sales and, for an uncommon few, a place in the zeitgeist. For most writers, those kinds of dreams are deferred, sometimes forever. For Whitehead, who is just 49, they are a rare reality.

If greatness is excellence sustained over time, then without question, Whitehead is one of the greatest of his generation. In fact, figuring his age, acclaim, productivity and consistency, he is one of the greatest American writers alive.

Photograph by Wayne Lawrence for TIME

Arch Colson Chipp Whitehead went by Chipp as a kid, then deeming the name too “preppy,” switched over to Colson at 21. He learned only a few years ago that Colson, the name of his maternal grandfather, was also the name of an enslaved Virginia ancestor who purchased his and his daughter’s freedom.

Whitehead was the third of four children, with two older sisters and a brother 10 months his junior. His parents owned an executive recruiting firm, a business that allowed them to send their children to elite private schools, travel and — as he writes about in his most personal book, Sag Harbor — spend summers in the Long Island village that serves as a vacation spot for affluent blacks. But his home was not without trials. “My dad was a bit of a drinker, had a temper,” Whitehead says. “His personality was sort of the weather in the house.” Whitehead’s father wasn’t close to his extended family; however, he was vocal about his views on freedom as it pertained to his people. “He was apocalyptic in his racial view of America,” says Whitehead. He adds that his father held the outlook “for good reason,” suggesting it also informs his point of view.

Whitehead explains that in response to his father’s moods, he and his brother, who died last year, retreated into comics, books, music and TV. He played a lot of Dungeons and Dragons and the video game Wizardry — he still turns to video games in his down time — and for a short period practiced in a band called Jose Cuervo and the Salty Lemons. (Go figure, they only staged one show.) Gen X-er that he is, he loves Sonic Youth’s “Daydream Nation” and Prince’s “Purple Rain,” so much so that he listens to them while writing the final pages of his books.

Around high school, Whitehead was also reading fiction that would influence his decision to pursue writing — Gabriel García Márquez’s One Hundred Years of Solitude and Jean Toomer’s Cane; also Shirley Jackson’s story “The Lottery” and a chapter of Ralph Ellison’s Invisible Man. Whitehead recalls thinking he might one day do what Ellison did.

A self-described “diligent student,” he went to Harvard. Imani Perry, now a Princeton professor of African-American studies, attended Yale and remembers seeing Whitehead at a gathering for black Ivy League students in their college days. “He was definitely engaged socially but also kind of above the fray,” recalls Perry. “He seemed reflective and interior.”

Whitehead thought he’d become a “super experimental writer.” The Harvard English department, which he describes as “conservative” in those days, didn’t teach many classes on the modern American novel, so Whitehead studied it on his own, reading books by innovators like Thomas Pynchon and John Barth as well as black absurdists like Ishmael Reed.

After college, he returned to New York in 1991 and, jobless, lived with his parents for a time. He started writing for the Village Voice. Meanwhile, he completed his first novel manuscript, about an ill-fated child star, and landed an agent. More than 20 rejections later, she dropped him. “I became a writer not through wanting to write comic books or being a journalist,” he explains. “But just saying I’m going to do it again. No one else is going to write it for me, so I might as well start.”

Nicole Aragi, now his longtime agent, sold his second attempt at a novel, The Intuitionist. Whitehead’s debut, about a black female elevator inspector, was a critical success and drew the attention of a future collaborator. “Pre-Moonlight, pre-Beale Street, I had dreams of turning his first book into a movie,” says Jenkins. “And there was no way that was gonna happen because you know Colson’s always been big-time, and it’s taken me awhile to catch up to him.”

Whitehead doesn’t present like somebody who believes he’s big-time. Matter of fact, in the several hours we spend together, I don’t detect an air of self-importance. To his credit, he also hasn’t chased the commercial success possible for writers who when their work finds a large audience make more of the same. Instead, he’s chosen the tougher route, following the imperatives of his interests and imagination to produce singular work. Then wagered the same risk again.

Lest you think Whitehead spends his days alone in his study, he lives a family-oriented day-to-day. Raising his 14-year-old daughter and 5-year-old son with his wife, literary agent Julie Barer, he writes while his kids are at school and is the go-to parent for cooking dinner. Picture him dropping his boy off at pre-K and then writing one of those great monologues for Ridgeway, the slave catcher in The Underground Railroad: “I prefer the American spirit, the one that called us from the Old World to the New, to conquer and build and civilize. And destroy that what needs to be destroyed. To lift up the lesser races. If not lift up, subjugate. And if not subjugate, exterminate.”

Whitehead doesn’t dawdle. "I only have so much time," he says. "I should probably start another book before I’m struck by lightning or something." Wayne Lawrence for TIME

Oh, I have my theories on the critical reception to creative work exploring the institution of slavery. Without writing a mini dissertation, I’ll say it’s the perfect subject for at once affirming white privilege and assuaging white guilt. Still, subject alone does not make a great book. It’s what the writer does with that subject: in this case, tell a story that calls for a reckoning with the lasting ills of America. And it’s a testament to Whitehead’s talent that he turned a subject of national turmoil into an indelible work of art, one that could’ve only been made by him.

If The Underground Railroad told of how whites asserted their privilege and power over blacks through slavery, then in the new novel, The Nickel Boys, Whitehead turns his focus on the trauma its descendants have inherited. Set at the Nickel Academy reform school in the ’60s, the novel centers on two pupils, Elwood and Turner, who debate the possibilities for surviving a racist America. The school was based on the real Arthur G. Dozier School for Boys in Florida, notorious for its mental, physical and sexual abuses, which was closed in 2011; dozens of bodies have been found buried on the school’s grounds. Whitehead intended to visit but never made it. “The further I got into the book, the more depressed and angry I got about going to the place, until I would only go there if I had a can of kerosene and a match,” he says.

Whitehead saw himself in the disparate views of Elwood, an optimist who treats Martin Luther King Jr.’s words as gospel, and Turner, a cynic who evokes a rage and disillusionment that will resonate with many readers. He drew on that tension to bring the characters to life. “A piece of art really works when you see yourself in the main characters and you see a glimpse of yourself in the villains,” Whitehead says. “You see yourself in the minor and major characters where, but for a quirk of fate, you could be in there with them — that could be growing up as an African-American male in America.”

De jure Jim Crow ended with President Lyndon B. Johnson signing the Civil Rights Act of 1964 and the Voting Rights Act the following year, but even a slight probe of the United States — its neighborhoods, school systems, criminal-justice policies, re-emergent brazen hate crimes — turns up evidence aplenty that the evil heirloom of Jim Crow endures.

Whitehead knows what every black person should: that no amount of accomplishment or wealth can exempt one from that legacy. “I carry it within me whenever I see a squad car pass me slowly and I wonder if this is the day that things take my life in a different direction,” he says. “It’s there with most young men and women of color. It’s with us when politicians can appeal to people’s most base prejudices and against their economic interests because their fears, their irrational weaknesses, are more powerful than doing what’s right for them. It’s with us when scheming men are trying to figure out how to gerrymander their state to deprive brown people of their vote, to figure out which polling places to close so that people have a difficult time getting time off and traveling to register or vote. A lot of energy is put into perpetuating the different means of controlling black people under slavery, under segregation and now under whatever you want to call this contemporary form.”

Historian Nell Painter, a professor emeritus at Princeton, describes a “purposeful ignorance” about the most painful aspects of our history. “Many Americans can’t say the word black without sort of stumbling over it first,” she says. “So, it’s a challenge that so many American readers avoided, forever, and that many are now ready to face.” The Nickel Boys dramatizes the truth of Jim Crow and its reverberations, while at the same time presenting a story that’s hopeful, or at the least honest, about the human capacity to outlast the terrors of injustice.

Whitehead has proved his mastery over his craft. Yet it’s taken time for him to accept his own place in the literary world. About a decade ago, he ran into Toni Morrison — who he says is the Great American Writer — on the Princeton campus. She invited him for coffee. “I was like, ‘I don’t deserve to have coffee with Toni Morrison. That’s ridiculous,'” he says. He never went through with it. “I was too embarrassed that she invited me. It’s like getting someone else’s mail.”

Would he have accepted the invitation today? “I’m less self-conscious now,” he says. “I have fewer hang-ups.”

A couple days after meeting him in Harlem, I head to Whitehead’s new second home in East Hampton, which I will learn is 4,000 sq. ft. and sits on two acres of land. Pulling up, I can see him through the floor-to-ceiling windows that look into the kitchen. There he is standing over the stove. He waves and hustles to the orange front door. He’s dressed in a T-shirt, blue jeans and red Chuck Taylors — all the right amount of worn in. Whitehead is making jerk smoked pork (his smoker is beloved) and potatoes and offers to share the recipes. Lunch won’t be ready for a while, but he’s got snacks.

Hours later, he serves me a plate. He warns of spiciness and pours me a glass of water. While he busies himself elsewhere in the house, I eat the meal alone in his kitchen, feeling thankful for his graciousness and culinary skill. If you’re wondering, the food is scrumptious.

I’d seen Whitehead around New York a few times at literary events, and because we hadn’t conversed, hadn’t exchanged a handshake or dap or the universal black man’s acknowledgment known as “the nod,” I’d judged him a certain type. But our conversations have been easy, and his current hospitality feels real, and well, call me a softy, but this fast, it’s almost as if he’s a literary-big homie I ain’t seen in some Sundays.

Some writers impress critics and win accolades; others tally robust sales. Whitehead is the rare writer who’s accomplished both. “I was definitely broke,” he admits. “Most of my life I’ve been living check to check.” But please believe he ain’t living check to check no more. He tours me around the house, a stunner. Upstairs, he shows me a master bedroom as big as my old Harlem apartment, and out back there’s an in-ground swimming pool. His home is what I was hoping it would be because, as far as literary careers go, he’s a paragon, and I for one welcome proof that what he’s achieved can earn such a life.

We sit down to chat in his office, and he offers to show me an outline from The Underground Railroad. He opens the file, and points to the beginning. There are no roman numerals or numbers or letters, only sentences, many of which describe things I remember from the book. “I know the beginning and the end,” he says. “Then it gets fuzzy, and things drop in and out.” He’s already working on his next project, one he started before writing The Nickel Boys: a crime novel set in Harlem in the 1960s.

As we talk, I notice markings on one of the moldings. He later tells me they’re dated height measurements of the children of the home’s previous owners. It strikes me that Whitehead didn’t erase them but rather has added an entry for his son. That small decision might explain some of his writing practice, the act of taking old forms or subjects and filtering them through his imagination, of holding the confidence that one needn’t try to erase what’s come before to make something new.

Whitehead steps away, and while he’s gone I lift medals to feel their weight, pull a framed award certificate off the shelf and read its small print, flip through the stack of framed posters. I wonder what it must feel like for him to work in this space, to look over at the trappings of his accomplishments, to glance out the window at the forest that is his yard. It strikes me that it might’ve been tough for Langston Hughes and Whitehead’s other forebearers to fathom his achievements, that he just might be beyond their dreams.

Jackson is the author of The Residue Years and Survival Math. His Twitter is @MitchSJackson.

This appears in the July 08, 2019 issue of TIME.

Contact us at letters@time.com.