Colson Whitehead’s ‘Underground Railroad’ led him to Jim Crow Florida

Elwood and Turner, the adolescent protagonists of Colson Whitehead’s new novel, The Nickel Boys, become fast friends at a brutal, segregated reform school in Jim Crow-era Florida, but they are opposites. Elwood is bookish, optimistic and gullible. While working in a hotel kitchen before being sent to the Nickel Academy, Elwood gets duped into dishwashing “competitions,” ending up doing the work of his older, wised-up peers. At home, he listens again and again to a Martin Luther King Jr. oration — “containing all that the Negro had been and all that he would be” — and after the Brown v. Board of Education decision he waits expectantly, and in vain, for a black man to enter the hotel’s whites-only dining room and sit down for a meal.

Turner is already at Nickel when Elwood arrives, so he knows how the world works. Turner, Whitehead writes, “was always simultaneously at home in whatever scene he found himself and also seemed like he shouldn’t have been there; inside and above at the same time; a part and apart. Like a tree trunk that falls upon a creek — it doesn’t belong and then it’s never not been there, generating its own ripples in the larger current.”

Whitehead, who is 49, says he sees himself in both boys. We were having lunch at a diner on New York’s Upper West Side, where the author spent his high school years. He recently moved back to the neighborhood after 18 years in Brooklyn. “It’s really boring and the food’s terrible, but we don’t go out much and my wife’s parents live here,” he said.

The idea for the novel came in 2014, after Whitehead came across news reports about the discovery of numerous unmarked graves at Florida’s Arthur G. Dozier School for Boys, which serves as the model for the Nickel Academy. Throughout its 111-year history, Dozier, which shut down in 2011, was known for brutality: beatings, rapes and, yes, murder. Dozier was segregated, but there was one building, “The White House,” where both black boys and white boys would be taken for beatings and worse.

When he first read these accounts, Whitehead was writing The Underground Railroad, which was published in 2016 to wide acclaim. It has since won both the Pulitzer Prize and a National Book Award, and it is being adapted into an Amazon series by Barry Jenkins. The novel follows an enslaved woman’s escape from antebellum Georgia. It’s a haunting, brutal, hallucinatory journey set against the backdrop of several fantastical conceits, including the central one: What if the Underground Railroad were, in fact, a real subterranean railroad?

“Usually I do a serious book and a more jokey book,” Whitehead told me. “The Nickel Boys was a departure because I had just finished Underground.” He was planning to write a detective novel, but current events intervened.

“It was the spring of 2017 and Trump was trying to get his Muslim ban, and I was angry and discouraged by the rhetoric you’d see at his rallies,” Whitehead said. “I hadn’t written anything for a year and a half, and it was time to get back to work. I could do the detective novel or The Nickel Boys. I thought that with the optimistic figure of Elwood and the more cynical character of Turner I could draw on my own confusion about where we were going as a country.”

Unlike with The Underground Railroad, for which Whitehead drew upon stories from former slaves collected by the New Deal-funded Federal Writers’ Project and other historical accounts, there are living survivors of Dozier.

“It was a horrible place,” said Jerry Cooper, president of The Official White House Boys Association, an alumni group of sorts for the abused. Cooper, who is white, said, “We didn’t have interaction with the black boys, aside from maybe when we saw them bringing produce to the cafeteria. They were in one area of the campus, and the whites were another. And if the guards caught you interacting, you’d be sent to the White House — no matter your color.”

Cooper, who was at Dozer in 1961, told me African Americans may have had it worse overall because their work detail involved toiling in fields under the burning Florida sun. “But there wasn’t any difference in the beatings,” he said.

Cooper recalled a 2 a.m. trip to the White House, where he was placed facedown on a mattress and given 135 lashes with a 3-foot leather strap. “I passed out at around 70, but a boy waiting outside for his punishment kept count,” he said. “I still have the scars. That night I realized what it must have been like to have been a slave.”

But neither Cooper nor his ancestors were slaves. Many of Whitehead’s ancestors were.

His mother’s side of the family hailed from Virginia. Her father was named Colson, as was another enslaved forebear, “who bought himself out of slavery,” Whitehead said. His father’s side of the family was rooted in Georgia and Florida — “there’s an ancestor on that side from whom I got the name Turner” — while his paternal grandmother emigrated from Barbados through Ellis Island in the 1920s.

“A lot of my family history is lost to slavery,” Whitehead said. “And some that’s out there, I didn’t know at the time of writing Underground.” After it was published, some of his cousins reached out to chide him. “They’d say, ‘Didn’t you know about this, and this and this, about our history?’ ”

Whitehead grew up in Manhattan to upper-middle-class parents and spent his summers at the family vacation home in an African American enclave of Sag Harbor, New York. “The first generation came from Harlem, Brownstone Brooklyn, inland Jersey islands of the black community,” writes Whitehead in his fourth book, Sag Harbor (2009), a semiautobiographical novel that captures a nerdy, carefree adolescence. “They were doctors, lawyers, city workers, teachers by the dozen. Undertakers. Respectable professions of need, after Jim Crow’s logic: White doctors won’t lay a hand on us, we have to heal ourselves; white people won’t throw dirt in our graves, we must bury ourselves.”

Whitehead’s mother’s family owned three funeral homes in New Jersey, and his parents owned an executive recruiting firm. His mother and father became the parents of two daughters, then Colson and a younger brother. On paper, it was a Cosby Show existence. But as Whitehead recently told Time: “My dad was a bit of a drinker, had a temper. His personality was sort of the weather in the house.” (There are two sad examples of such temper in Sag Harbor, including one in which the father repeatedly punches young Benji, the protagonist, in the face as an ill-conceived demonstration of standing up to racial taunting.)

After attending private schools in New York City, Whitehead went to Harvard. Growing up, he had immersed himself in comic books and horror films. “I wanted to write horror, science fiction and comic books,” he said. “A lot of writers my age had similar influences,” he added, citing Michael Chabon, Junot Diaz and Jonathan Lethem. “Then, in late high school and college, I started to think, Maybe I don’t have to write about werewolves.”

He was approached by another young African American writer at Harvard, Kevin Young, who is now an accomplished poet, the poetry editor at The New Yorker and director of the Schomburg Center for Research in Black Culture. “I was working with a friend on reviving a black magazine from the 1970s, Diaspora, and she had met Cole and said he could be our new fiction editor,” Young said. “We hit it off instantly, and I published his first story.”

After college, Whitehead worked for five years at The Village Voice, eventually becoming the television critic. It was there he met writer-photographer Natasha Stovall, whom he married in 2000. (They later divorced.) He wrote a novel, but it was turned down by publishers and his agent dropped him.

“I was depressed,” Whitehead said. “But I wasn’t going to get a real job, and no one was going to write my books for me, so I understood I needed to get going. That’s really when I became a writer.”

His second effort, The Intuitionist, was published in 1999 and is set in a simulacrum of fedora-era New York, where there’s a war brewing within the city’s powerful Department of Elevator Inspectors. The protagonist, Lila Mae Watson, the first black female inspector in the department, is tasked with investigating a mysterious elevator crash. The book was well-received, including comparisons to debut efforts by Joseph Heller and Toni Morrison.

In 2001, Whitehead published John Henry Days, a multilayered, encyclopedic narrative thematically tied to the legend of John Henry, the railroad laborer who is said to have bested a steam-powered drilling machine. The following year he won the MacArthur Foundation “genius” award. Other novels (Apex Hides the Hurt, Sag Harbor, Zone One), a historical exploration of his city (The Colossus of New York) and even a poker memoir (The Noble Hustle, spun off from a Grantland article), followed. But it was The Underground Railroad (with a boost from Oprah’s Book Club) that launched Whitehead into literary stardom.

“It’s been remarkable to see Cole’s journey both in terms of his writing and as a person,” said writer and publisher Richard Nash, whom Whitehead met at Harvard and to whom The Nickel Boys is dedicated. “I remember going to one of his readings for his first book, The Intuitionist, at a bookstore in Soho. His hands were shaking, he was so nervous. And now I fully expect in a few years you’ll see his name crop up on the betting lists for the Nobel Prize.

“Especially with the last two books, it’s clear that’s where he’s headed.”

Whitehead has his critics. In a stinging review of John Henry Days, The New Republic’s James Wood (now at The New Yorker) pointed out instances of sloppy writing, such as using “deviant” for “divergent” and “discreet” when the intended meaning was “discrete.” Wood went on to note that Whitehead “tends to excessively anthropomorphize his inanimate objects” to “squeeze as much metaphor from them as he can.” Whitehead returned the favor a few years later when he satirized Wood in a Harper’s Magazine essay.

But Whitehead’s style has evolved, and his writing has become more precise. In The Nickel Boys, the anthropomorphization is sparing and powerful, as when he describes the shackles employed on defenseless boys who were beaten to death: “Most of those who know the stories of the rings in the trees are dead by now. The iron is still there. Rusty. Deep in the heartwood. Testifying to anyone who cares to listen.”

After our lunch, Whitehead said he was considering making chili for his family — his wife, literary agent Julie Barer, 13-year-old daughter, Madeline, and 5-year-old son, Beckett. “It’s hot, but there’s something about chili, it’s so hearty and satisfying,” he said. Cooking is a passion, and he’s been perfecting his meat smoking skills at his new vacation home in East Hampton.

When he was writing The Nickel Boys, Whitehead said, he was struck by the parallels between the 1960s and today in terms of race relations. As a father myself, I was curious about how he broached the subject of race with his own children.

“It comes up more when we talk about police,” he said. “[My son is] really into cops and robbers. So when we’re walking around and he sees a police car with its sirens blaring, he’ll say, ‘They’re going to catch a robber.’ And I’ll say, ‘Maybe it’s an innocent man. Maybe it’s just a dark-skinned guy driving a nice car.’ ”

Whitehead couldn’t remember when his daughter first became aware of race — when she discovered that, to borrow a phrase from one Nobel Prize-winning writer, the world is what it is.

“That was a long time ago, and I can’t recall a particular moment,” Whitehead said. “But the thing is, everyone figures it out sometime.”