Guarding the Prison, Guarding the Press

Ted Conover swings his leg over a metal traffic barrier that guards the edge of a parking lot and crunches his way through foliage to the top of a hill. He surveys the view below on this balmy fall day in New York State. Geese fly in formation up the Hudson River. Golden maple leaves drop from trees overlooking the Palisades. At the bottom of the hill, behind a three-story wall of unfinished concrete, lies one of the world's most famous prisons: Sing Sing. "There's B block, that huge brick building." Conover points to a massive structure. "You can often hear the PA system on the blocks on summer days when the window is open: 'FIRST GALLERY! ON THE CHOW!' But today -- well, I guess any day -- you can't tell what it's like on the inside from here."

Sing Sing, like the entire American prison system, defies observation from the outside. Conover probably knows this better than anyone. A contributing writer for The New York Times Magazine and author of three previous books of participatory journalism, Conover wanted to investigate the heart of what he calls "America's incarceration crisis." His investigation became the controversial book "Newjack: Guarding Sing Sing." "I believe strongly in the need for prison reform, but I didn't want to write an Op-Ed. I wanted to give people information, take them somewhere they couldn't go otherwise," he explains. As he writes in the book, "There is little that engages my imagination like a wall." Conover has walked this ground before, immersing himself in situations concealed to the public, with such books as "Coyotes," about his travels with Mexican illegals, and "Rolling Nowhere," about riding the rails with hobos. This sort of work is his claim to fame. But in this case, Conover found two walls -- the gargantuan rough gray structure that secures prisoners at Sing Sing and the invisible barrier that keeps outsiders from understanding what goes on there.

Conover found that getting into Sing Sing was as difficult as getting out. First he was snubbed by the state bureaucracy. Then he tried talking to the guard's union representatives but quickly sensed that their collegial vow of silence about the details of their brutal daily lives wasn't something to be broached. Unable to break through the system, Conover became part of it. Literally. In order to understand the psychology and experiences of the corrections officer, he enrolled in the Department of Correctional Services (DOCS) training academy, braved seven weeks of boot camp and became a rookie prison guard -- a "newjack."

The legacy of his experience is twofold. Conover, the writer, published a book that has spawned controversy (and censorship) throughout the DOCS. But Conover, the guard, still has fantastical nightmares about being attacked by inmates -- this almost three years after he last entered the hulking mass of B block.

Relentless Reporter

All good writers immerse themselves in their work, but Conover's relentless devotion to his reporting and the risky methods he undertakes to accomplish his task have raised ethical questions. His and his book's high visibility ("Newjack" graced the cover of The New York Times Book Review and Conover has appeared on Oprah, for example) lend attention and gravity to these concerns. Did he misrepresent himself in securing a position at Sing Sing? Did he cross a line in reporting a story where his cover as a guard required him to use force against many of his subjects, the prison's inmates? Can we separate Conover, the guard, from Conover, the journalist? And, perhaps most important, is it possible for the media to infiltrate the inner workings of prison life in any above-the-table role without taking these ethical risks?

To write "Newjack," Conover had to give himself over to the work in a way that, under the surface, seems almost antithetical to journalism. The psychology of a corrections officer is at odds with one of the requirements of good journalism -- that the writer establish genuine, human contact with his subjects. A successful guard, he explains, does exactly the opposite. "You need to lump people together, make an effort not to get to know them. The job requires that to protect yourself," he says. This is especially strange when one considers that Conover's best-regarded work consists of stories of close relationships he has developed with his subjects. He has made a career of forming bonds with strangers in situations most people would never choose to be in. "I admit it," he laughs. "I'm part of the great American freak show."