In 1997, sporting a crew cut some friends misconstrued as "downtown hip," Ted Conover drove daily from his Bronx home to the infamous Sing Sing prison, the tension of his guard's job compounded by the enforced secrecy of his writer's quest. Last month, his hair again civilian-length, ex-Correctional Officer (C.O.) Conover took PW on the half-hour drive, his shiny Honda Civic (complete with child's seat) having supplanted the rusty Toyota Corolla he once drove.

"I thought it would make me nervous," Conover declares avidly of the return trip, "but it reminds me of OJT [on-the-job training], the excitement of getting into the belly of something people try so hard to keep secret." He hasn't been back in a year, during which he finished Newjack: Guarding Sing Sing, published this month by Random House, an inside view of guards, inmates and the peculiar institution of prison.

After the nearly 11 months he spent in the system, from training through his nine-month term as a "newjack" (new C.O.), Conover still confided only in his wife and a few friends. Not until the book was vetted could he exhale. Random's lawyers had to ask if Conover faked his background when he applied for the job--a tactic he chose only after he was rebuffed as a reporter. In fact, Conover presented a truthful, if edited, résumé. It left out his three books of anthropological journalism (Rolling Nowhere; Coyotes; and Whiteout: Lost in Aspen) and his status as a New York Times Magazine contributing writer, but included his Amherst degree and his job as an Aspen Times reporter, part of his Whiteout research.

"I hope officers see the book as empathetic," says Conover, whose account of his soul-testing stint--from Sing Sing's barbaric "Box" (isolation unit) to its bittersweet visiting room--notes occasional brutality and regular rule bending, even his own. "The problem is that correctional departments have a bunker mentality. Maybe it sounds like a double standard, but I had to keep secret because there's no other way to learn about a prison." As Conover drives through Westchester, suburban comfort gives way to "Historic Ossining" banners, then rundown streets and the high walls of Sing Sing. A stoic woman sits on a curb, "probably waiting for a conjugal visit," Conover observes. Near a wall is a warren of trailers where some C.O.s bunk; officers train at Sing Sing before transferring to upstate prisons closer to home. Conover points to a guard tower and the white industrial buckets in which guns are delivered, as officers generally can't bring weapons into prison. Skirting a dark "C.O. bar," Conover pulls past the train station and parks.

Then, on a picnic bench just in front of the fortress, we sit down to talk. Hardly imposing at five-foot-eight, 148 pounds (on his prison ID), Conover, 42, dresses casually in blue jeans and red corduroy shirt. Open, even earnest--qualities for which some of his earlier writing has been both praised and criticized--he radiates a fierce enthusiasm for his work. Conover even considers friendships with fellow writers "a guilty pleasure, because I feel a writer's real job is to be out there with people who are strange to you."

In Rolling Nowhere, Conover immersed himself in the not-so-romantic world of hoboes; in Coyotes, he shadowed illegal aliens from Mexico.In Whiteout, he tested his own susceptibility to the comfort and glamour of Aspen. Also consider Conover's magazine work on subjects like AIDS and African truckers, and it becomes clear that his career engages not only class but also--as he writes in Coyotes--"the subversive idea that a human is a human, and that human beings everywhere, with a little effort, can come to understand and even like each other." In Newjack, that idea is tested by Conover's effort "to work as a prison guard and not fail to fit in. The main difference between the recruits and me was the benefits I had."

What about the inmates? "That's a harder question. I'd like to think I'd never commit violent crimes," he says, "but the key line in Newjack is, 'The longer I spent in Sing Sing, in fact, the easier it was to imagine anybody, anywhere, committing practically any crime.' Sing Sing has made me a bit more pessimistic.... It's like reading the darkest passages of Robert Stone, day after day. It almost becomes hallucinogenic." Unlike Stone's fictional creations, prison--"a world of adrenaline and aggression" (to quote Newjack), filled with racial tension--is real: "We pay millions and millions of dollars. It should make more sense than it does. It should aspire to more."

Rehab?

"Leave off the 're.' Some people were never habilitated in the first place."

A Long Leash

Frederick King Conover III grew up in a comfortable Denver family, the oldest of four children, his father a lawyer. Granted a long leash as a teen, he honed his Spanish on summer trips to Spain and Mexico, and took a long bike trip with a friend after high school. He was bused to a newly desegregated high school in the ghetto, 50% black, 40% white, 10% Hispanic. "It was not 'our' school," Conover muses. "That's probably where my whole interest in class and cultural difference got sharpened.

"This book is a definite echo of that, a whole different world 10 miles from my house. And I wanted to know about it. We all understand that it's good to have advantages. But privilege can put blinders on you."

Frustrated by clubby Amherst, Conover took some time off, first working as a VISTA volunteer in inner-city Dallas. Then, intrigued by the hoboes he met while biking, he spent four months on the rails for his Amherst anthropology thesis, discovering instead a world of distrust and displacement, with daily struggles for dignity, safety and food. Back at school, his friends were less interested in anthropological analysis than his personal adventure, wanting to know whether he felt hungry or homesick. Drawing on a section of his thesis, Conover wrote a first-person article for a student magazine. After the Amherst alumni magazine picked it up as a cover story, Conover appeared on the Today show, and decided to write a book.

Connecting to agent Sterling Lord through New York Timesman Jack Rosenthal--a friend of a friend--Conover garnered a contract with Viking. Published in 1984, Rolling Nowhere got him into People magazine and won him critical praise for his resourcefulness. At the time, Conover was in the midst of two "somewhat wasted" years as a Marshall Scholar at Cambridge University. The English department's lit crit emphasis deterred him, so he pursued Latin American studies instead. He then began a new adventure, following a thread in Rolling Nowhere, his encounter with plucky Mexican migrants who treat the search for work as la lucha, the fight.

To research Coyotes (1987)--named for the shady characters who spirit migrants across the border--Conover picked oranges, went on long road trips, hung out in a Mexican village whose men regularly trek north, and even endured a terrifying arrest by Mexico's notorious judicial police. Coyotes has comic aspects, as in Conover's feverish efforts to steer migrants through a shiny, alien airline terminal. Lord sold Coyotes to Random House, where the book went through three editors; ultimately, David Rosenthal made it the opening title in the Vintage Departures travel lit series. Coyotes--which treats the migratory phenomenon as neither crime nor tragedy, as one reviewer noted--is Conover's only previous book still in print, selling some 60,000 copies, mainly for coursework.

Rosenthal also published the playful, ruminative Whiteout (1991), in which Conover worked as a Mellow Yellow taxi driver, house-sat, party hopped and met angel/devil local icons like John Denver and Hunter S. Thompson. Though Conover wound up wondering about the town's smugness, he acknowledges his own complicity.

Conover moved to New York City to write Whiteout, joining his magazine editor girlfriend (and now his wife). In 1992, aiming to amplify a brief report from an AIDS conference--that African truckers were key vectors for AIDS--Conover got an assignment from the New Yorker's Robert Gottlieb. "What an amazing life, to be a long-distance truck driver in Africa. And I thought it was a story I could research, because of my willingness to hang out." After three months studying Swahili, he flew to Nairobi and Mombasa. Then Conover spent five weeks on the road, concluding--in a piece published by Gottlieb's successor, Tina Brown--that the truckers' fatalism might be a reasonable response to the strictures and strains on their lives.

Finding a Way In

As early as 1992, Conover began researching prisons, but his effort to follow a recruit through training--"a good magazine story"--was resisted by New York prison officials. So he filled out an application in 1994. When he entered the training academy three years later, he absorbed the contradictions of the system, learning, for example, how only the techniques of riot control, and not the ethics, were taught. At Sing Sing, Conover kept his union diary in his breast pocket, and behind that a pad he used to secretly take notes, when he was alone in an office or in the cellblock. Back home each night, he'd type five or six pages of single-spaced notes--500 in all. "The job was full of discretionary power and the decisions about how to use it were often moral," he writes, concluding that good guards use dialogue as much as raw force.

For five months after he quit, he read deeply in Sing Sing and correctional history. Then he began writing, hewing to a 9-to-5 schedule. Though he had written most of Whiteout and the Africa piece in the Writer's Room in Greenwich Village, Conover had since become a father of two young children and now writes at home. "It was challenging to figure out how to order the experience," Conover says, pointing to his diary and the uneven pattern of assignments--psych unit, mess hall, transportation detail, B-Block (a mammoth building of cell galleries). So he organized his major chapter about prison work not by time but by job. And by September, with some seniority in this training facility where all newjacks are first assigned, Conover bid B-Block, landing himself months of continuity--and a smoother end to his story. To fill out the narrative, he inserted a long chapter on Sing Sing's tortured history.

Random House had an option on his next book, though Rosenthal had moved to S&S. Agent Kathy Robbins, who had represented Conover since he moved to New York, agreed the proposal shouldn't be shopped, so she targeted Random editor Daniel Menaker. Conover praises "Menaker's meticulousness" and his wife Margot's contribution as first reader.

Conover reflects: "First-person nonfiction is tricky. It's a combination of the voice you use, the self-revelation you offer, and the more discursive material that's important. From the beginning, I've always wanted my subject to be other people, with me as a character. But I'm less interested in being a character now than a narrative presence. I said a lot about myself in Rolling Nowhere I guess I don't need to repeat." And unlike in Coyotes, when he broke voice in a heartfelt afterword to argue that most migrants would make good neighbors, Conover now trusts the reader more: "Don't say some of the guards are bad, most are fine; let the reader meet them."

Conover, who aims at a conversational prose style, mostly reads fiction when he writes: "I'm mainly interested in storytelling, and fiction writers are better." For well over a decade, he's been working on a novel, more off than on. It began as the story of a young man, Mexico and risk, but "the two times I've tried to restart it, I've watched it turn into a new novel." However, he repeatedly finds "something of interest in the actual world that hijacks my interest from the fictive world."

Can Conover top himself? "I think that more than seeking out risk, I'm looking for stories other people haven't thought to do." As a father, he's warier now, too. As he writes in Newjack, the tensions of guard work so parallel those involved in parenting small children that he once snapped, performing a "use of force" when his young son "refused to comply."