Walking a Mile in the Shoes of a Sing Sing Guard

Ted Conover got clocked in the head, screamed at daily, humiliated by society’s rejects for seven months straight and given the silent treatment by his wife--all in the name of experiential journalism.

The author has just finished a book about what it’s like to be a guard at one of the most notorious prisons in the country. “Newjack: Guarding Sing Sing� (Random House) is the boldest project that Conover has pulled off, no small claim for a writer who has spent his career penetrating deep into shrouded territory and emerging with spicy yarns.

“Correction officers, like police officers, have their secrets,� Conover said. “There’s the public story versus the true story, the one that only the participants, the insiders, know. I wanted that story.�

Every morning at 6, the author slipped on his guard uniform, looped a baton through his belt and trudged into the miserable, crumbling brick confines of 170-year-old Sing Sing Correctional Facility in New York. He had a three-part mission: maintain order among hundreds of violent misfits, stay safe and soak up--undercover--the impressions of the guard experience.

His duties were often ugly (think intimate body searches and wrestling prison-sculpted inmates to the ground) and the pay was lousy--$23 grand a year. His cover, at times, was tough to keep.

“Conover, man, you walk different from the other guards,� he remembered one especially perceptive inmate saying. “What you do before here?�

Conover, 42, had done quite a bit of adventuring. Once a student of anthropology, he’s carved out a niche as a writer by using participant observation methods to offer rich, gutsy accounts of unlikely subjects. His first project, at age 20, was on hobos, and he spent a year riding the rails before writing a book called “Rolling Nowhere.� Next he traveled thousands of miles with illegal immigrants to produce “Coyotes.� After that he became a cab driver in Aspen, Colo., to glean a new take on the ski slope scene for “Whiteout.� He crisscrossed Africa with lustful truck drivers to chronicle the spread of AIDS for the New Yorker.

Conover lives in the Bronx, but a book tour recently brought him to Santa Monica, a place he fondly remembers as where a skinhead sucker-punched him at a doughnut shop a few years back for speaking Spanish with migrant workers. Things are better now. “Newjack,� named for the term inmates use to describe new officers, was published in May and has already created a stir, recently gracing the cover of the New York Times Book Review and scoring Conover an appearance on “Oprah� last week.

But the project exacted a hefty personal toll, forcing him to confront emotional and ethical issues.

“There was a lot of stress having two lives you can’t stitch together,� said the author, who didn’t tell anybody but his wife and literary agent what he was working on. “Being a writer is a lonely life to begin with, but when you add this layer of daily terror, alienation and fear of being discovered. . . . I don’t want to whine, but it was a lot to deal with.�

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Some journalists have taken shots at Conover for working surreptitiously. None of the guards or inmates in his book knew they were being chronicled. Roy Peter Clark, a senior scholar at the Poynter Institute, a Florida-based school for journalists, said such reporting methods raise questions of credibility.

“Even if he hasn’t lied directly, he’s used deception,� Clark said. “And if I know Conover has deceived all the prison guards, how do I know he’s not deceiving me?�

Conover had tried to do the book on the up-and-up, he said. But after he was rebuffed by New York state prison authorities in 1994 from following a new officer through training, he decided that becoming a guard was the only way he could portray them, Conover-style.

A spokesman for the New York State Correctional Services Department said officials didn’t have a problem with the book.

“We don’t even consider it undercover,� spokesman James Flateau said. “He went through the academy, passed all the tests and performed his duties like any other officer.�

The guard academy was trying enough, with hazing, mind-numbing rules, such as how to turn a corner without breaking your stride, and the mantra, repeatedly drummed into the recruits’ heads, that inmates were the scum of the Earth, the lowest of the low.

But the cell blocks--wow--that was a whole other world of staggering violence and chaos, Conover said. There, in essentially a Hobbesian state of nature, men instantly size each other up and assess who would win a fight. Guards can’t show a trace of fear because it attracts abuse from inmates and meddling from other officers. Convicted killers with nothing to lose lash out in unspeakable ways--such as hurling handfuls of feces at guards and spitting mouthfuls of urine.

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Into this maximum security world stepped Conover, a delicately built son of a lawyer who looks, from the side, a bit like JFK. He studied at Amherst College before winning a scholarship to Cambridge University. He stands 5 feet, 8 inches, and weighs 150 pounds. Many times he was challenged. Once, an inmate socked him in the head after Conover took away his mirror.

“Let’s just say I now know some people are bad,� he said.

The pent-up cellblock environment brought out an aggressive, violent side that Conover had never seen in himself. He learned tricks like yelling “stop resisting� to cover himself when he was roughing up a disobedient inmate and how to fudge the log books to conceal unwarranted discipline.

“You’re supposed to have aggression educated out of you,� he said. “But it’s still in there, like some atavistic trait in all of us.�

As the book points out, he did meet some redeeming souls, including a scholarly con nicknamed Powerful.

“I was so impressed by him, I felt myself getting close,� Conover said. “He was intuitive, intelligent, just too smart. If he wasn’t an inmate, we would definitely be friends. Isn’t that funny?�

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Conover wouldn’t reveal much about what he’s up to next. But he did volunteer that never again would he undertake a book that required such an elaborate disguise. That was one of the big differences between “Newjack� and previous projects in which he told the sources he was a writer. The tension, he said, led to long chilly stretches with his wife--since warmed up--frayed nerves and occasionally losing it with his two small kids.

But that doesn’t mean he questions his approach of “visiting� other lives, as he puts it.

“I love it, I absolutely love it,� he said. “I’m trying on a different outfit for each of these projects, and it’s thrilling. That’s basically what it comes down to. I mean, don’t you get tired of your own outfit sometimes?�

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Jeffrey Gettleman can be reached at [email protected].