The Undercover Life of Ted Conover

From Sing-Sing officer to meat inspector, working incognito is this writer's full-time job.

February 19, 2018 5:00 am
Sing-Sing with tower 1998. (Jennifer Klein)
Sing-Sing with tower 1998. (Jennifer Klein)

There’s a photo of Ted Conover worth examining. In it, you can’t see his face, and his torso is covered in a deep blue Corrections Officer uniform. But the important part is central, near his heart. Peeking out from his shirt’s front pocket is a tiny spiral notebook. The inside holds secrets.

During his 10 months as a C.O. in New York’s notorious maximum security Sing Sing prison, Conover was required to carry this small notepad. Ostensibly, it was to take down work-related information like requests from inmates, but Conover used it like a spy, jotting down ancillary information about the joint. The layout, a quote he overheard from a fellow officer, that kind of stuff.

At the end of his stint, he used the notes as the foundation for his book Newjack: Guarding Sing Sing, released in 2000. It told of his experiences as a guard, from his first days at the training academy, through the emotional trials of being an overworked cog in a grueling system. The photo of Conover and his notebook was the book’s front cover image.

Newjack cover. (Vintage Books.)

Over his three decades as a writer, Conover has utilized this technique of “immersion journalism” to unveil hidden truths about the psyche and logistics of underreported subcultures in a way that few other journalists have. He’s ridden freight trains (Rolling Nowhere: Riding the Rails with America’s Hoboes), serendipitously crossed the Mexican-American border (Coyotes: A Journey Across Borders with America’s Illegal Aliens), and toiled as a taxi driver and caterer in a Colorado boomtown (Whiteout: Lost in Aspen). These projects came from the same original question: I wonder what that’s like.

“I was interested in having adventures or unusual experiences before it occurred to me that I might write about them as a journalist,” Conover told me, over the phone.

His first dabble with the tactic was in Pamplona, Spain, where he got a three-month job at the famed sausage company. “I wondered if I could succeed in that environment, and what would I learn,” he said. While that experience never made it into a book, it set his course. And despite writing plenty of “normal” journalism in his long freelancing career, it’s the immersive style that he’s become known for. His latest book, Immersion: A Writer’s Guide to Going Deep, details lessons he’s learned about the craft.

Sing-Sing with tower 1998. (Jennifer Klein)

A good way to begin describing how “immersion journalism” works is perhaps describing what it is not: doing something, then writing about it.

“Your intent is to channel as best you can the experiences of other people,” Conover said. “I can write about working in prison purely from the lens of my own education and fear and discomfort, or I can focus on being there to learn what it’s like for people who have to be there all the time.”

This subtle shift in focus is perhaps best exemplified in “The Way of All Flesh,” a masterful piece in the May 2013 issue of Harper’s, about the months Conover spent as a USDA meat inspector in the Cargill Meat plant in Nebraska. In it, he focuses on the job’s logistics, like how a worker doesn’t destroy their own arm muscles through repetitive stress motions while examining how workers mentally deal with the monotony. “[My coworkers] know those things, and I’m ignorant, and I hope to learn,” he said. “That’s what I’m after, not the sounds that my heart makes when I think about the experience.”

Inside Cargill Meat Solutions. (Conover)

Similar to his gig at Sing Sing, while working at Cargill, Conover took notes on the sly. This mostly occurred during his three mandated breaks per day, when he’d scurry to an empty locker room to note anything that caught his eye; later that night, he’d expand them on his computer. The quick-notes were vital, as the most important details were also the most easily forgotten. “Like, the day the inspector they called Lefty taught me how to open a heart,” he said. “I finally did one well, and it opened like butter, and Lefty said, ‘one down, a million to go.’ It’s like, okay, I cannot forget he said that. That could’ve been the title of the whole piece.”

Noting this quote, utter perfection through everyday simplicity ,is immersion journalism at its core. As Conover details in Immersion, what he’s really doing is a close cousin to ethnography, summed up in that pursuit’s goal of making the strange familiar, and the familiar strange. “You want to notice that thing that strikes you odd, but doesn’t strike anyone else,” he said. “You get that from being new to a situation; to not being local.”

But there are dangers to such deep cover work. While they’re not the same physical tolls as, say, an FBI agent going undercover in a mob sting, the mental threats linger nearby. In Immersion, Conover discusses the career of Norah Vincent, who followed up Self-Made Man, a book about her 18 months disguised as a man, with Voluntary Madness, a book about her experiences in a mental hospital after suffering from depression following her immersion as a man. Conover himself has had an episode or two of blurring the edges of what ethnographers call “going native,” when someone who initially planned to simply observe begins actually living that life.

Ted Conover. (Photo by Margot Guralnick.)

Once, while at Sing-Sing, Conover came home from work and told his wife that he’d signed up to take the sergeant’s exam. In the moment, it made complete sense. The test is only offered once every five years, and if he was promoted, he’d make a cool extra $7,000 a year. Why not? “I thought you were going to quit after a year,” she said. “You never know,” was his response. She gave him a look. “You don’t?”

There was also the night he lost his temper with his kids.

“I was exhausted, and working my fifth or sixth day in a row with people who would not comply with my lawful directions. And I lost my temper, and spanked my son for the first time,” he said. “I was filled with shame and remorse, and a sense that my life had spun out of control. But was I ‘going native’ there? I don’t know. I certainly was not handling the challenges well.”

Despite these potential dangers to the author, Conover believes this form of journalism has extreme value, not only through its simple collection of data but by creating empathy through showing what life is like in another person’s shoes. It’s the goal that Conover reminds his students at NYU (he’s a professor at its School of Journalism) whenever they raise concerns about the fine line between telling other people’s stories and exploitation. “Awareness of one’s privilege is an essential starting point, but then, some people stop acting. They seem to conclude that because they’re privileged, they have no right to talk about anything,” he said. “On the contrary, because you’re privileged, you have an obligation.”

It’s also why Conover won’t stop filling out those job applications or otherwise trying out different lives to write about. I ask him if he has any other gigs he’s considering for future immersion projects. “I do, I do,” he says, a tone of hesitation in his voice. “And if we speak next year, maybe I can tell more.”

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