[This first-hand account of life inside Sing Sing is a C4 Great Read.]

Author: Ted Conover

Vintage Books, 2001

Filed under: Literary, Nonfiction

When Ted Conover wanted to write a book about the lives of prison guards, he started the way most journalists would: he asked the New York Department of Correctional Services (DOCS) for access. They denied him permission.

Considering Conover’s methods as a writer, he probably wanted to be denied. He’s an immersion journalist—one who embeds himself in the lives he wants to chronicle. He becomes one of his subjects. So after the DOCS said no, Conover became a “Newjack,” or a rookie guard, at Sing Sing, one of the most notorious prisons in the country. Newjack is the result of Conover’s experience.

At it’s core, Newjack reads like a travel narrative, and Conover’s experience is a journey. Conover guides us through the prison block, and shows us its inhabitants. He explains his training, and he points out how it left him mostly unqualified for what he would encounter within the walls. He tells us about Sing Sing’s infamous history—its menacing wardens, death chamber, and well-used electric chair—and he shows us how life inside is still just as nasty as it was when Sing Sing was the death penalty capital of the country.

Like any journey, Sing Sing holds several unforeseen complications for the traveler. Conover’s job is to maintain control and order, and quickly he finds that control and order aren’t easily accomplished. The men he must watch over will take advantage of any of his hesitations. It isn’t long into his first shift that he realizes the power and responsibility of his situation are weighty:

Gates had to be unlocked for the prison to function smoothly—and then, at the right moment, to be locked again. Sing Sing was a place of, probably, over two thousand locks, many with the same key. The cardinal sin, the one thing that you were never, ever to do, was lose your keys. A lost key could fall into an inmate’s hands. A lost key was a disaster.

Conover often finds himself treading a line of oppression, and he perpetually questions the moral implications of his decisions. And sometimes—like when an inmate punches him through the bars, or another one hits him with a handful of feces—he forgets about morality altogether. Conover’s struggle is one of balance, a search for the grey area between right and wrong, good and bad, and it will change the way he interprets the world for the rest of his life.

Newjack’s greatest accomplishment is Conover’s empathy, his ability to bring humanity to a setting that dehumanizes the inhabitants on both sides of the bars. The guards in Conover’s book are more than key-bearing enforcers. They are men and women with families, who struggle through the same moral uncertainties he does, who want to be good guards and good people, who mostly are in this line of work not because they enjoy being in charge but because they need the paycheck. The inmates on Conover’s cellblock aren’t faceless crimes or forgotten statistics. Many are genuine and likable, looking for someone to talk with. Admirably, Conover doesn’t shortchange the inmates he doesn’t like, or those who try to take advantages of his naiveté. He portrays them as individuals, as men, men who are motivated by making their monotonous Time go by more quickly, or at least differently than the day before.

Conover’s accurate portrayal of how prison feels is also great:

You feel it along the walls inside, hard like a blow to the head; see it on the walls outside, thick, blank, and doorless; smell it in the air that assaults your face in certain tunnels, a stale and acrid taste of male anger, resentment and boredom. You sense it all around in the pointed lack of ornamentation, plants or reason for hope—walls built not to shelter but to constrain.

It’s not a feeling most will ever experience or understand—a feeling of utter solitude complicated by utter hopelessness. Yet knowing that feeling will make companionship and hope more vibrant. Everyone deserves to know how that feels; it’s why, at least literarily, you should walk in the boots of a “newjack.”

Similar Reads: Stylistically: Coyotes (Conover), Thematically: Falconer (Cheever), The Execution of Tropmann (Turgenev)