Newjack: Guarding Sing Sing

by Ted Conover

Journalist Ted Conover gives a first-hand account of life inside the penal system. When Conover’s request to shadow a recruit at the New York State Corrections Officer Academy was denied, he decided to apply for a job as a prison officer. So begins his odyssey at Sing Sing, once a model prison but now the state’s most troubled maximum-security facility. The result of his year there is this remarkable look at one of America’s most dangerous prisons, where drugs, gang wars, and sex are rampant, and where the line between violator and violated is often unclear.

Genres: Nonfiction, Memoir, True Crime, Crime, Journalism, Sociology, Biography Memoir

352 pages, Paperback

First published May 2, 1999

About the author

Ted Conover, a "master of experience-based narrative nonfiction" (Publisher's Lunch), is the author of many articles and five books including Rolling Nowhere: Riding the Rails with America's Hoboes, Coyotes: A Journey Across Borders with America's Mexican Migrants, Whiteout: Lost in Aspen, Newjack: Guarding Sing Sing (winner of the National Book Critics Circle Award and finalist for the Pulitzer Prize), and, most recently, The Routes of Man: How Roads Are Changing the World and the Way We Live Today. He is a distinguished writer-in-residence at the Arthur L. Carter Journalism Institute of New York University."

Reviews

[Petra went to a party uninvited & ate cake]

The author was a journalist and anthropologist denied by the authorities all requests for entry to Sing-Sing in order to write about it, so he goes undercover and becomes a prison guard. And thereby exposes that guards and prisoners are opposite sides of the same coin separated by a very thin bevel indeed. The training might be all about sticking to rules, but the practice is all about bending them and sometimes crossing over to the other side.

The guards may have been trained to keep the rules but even a few hard guards are going to create enemies and that is going to create frustration, and since there are a lot of people with a very low tolerance level of that and a high propensity towards causing chaos and violence, it wouldn't work as a general policy. It's not quite the cliché 'rules are meant to be broken' as much as 'this is the ideal' but circumstances might dictate a better line of action.

Co-operation and working together, f\avours for the prisoners, yes you can go here, yes you can have five more books in your cell, no you don't have to have x as a cellmate, favours for the guards, speak to so and so, find out who started what etc. goes a long way to keeping the peace. It crosses the line but not in a bad way, when a prison officer says he will do a favour on the outside, buying some trivial item and sending it as a gift for example or bringing something small into the prison that isn't forbidden but isn't available either. The next step is to paying the officer to bring in a phone, drugs or the rest or having a relationship that is more than guard/inmate/friend but personal. That's when the guard is on the same side as the inmate, criminal, but still free. If you don't pay people well, and guards, are paid badly, then you lay the system open to corruption.

Why are there more drugs in prison than out of it? Because weed keeps people quiet. Stoned inmates are not up for violent riots, drunk ones are. Other drugs provide escape from being caged up for years at a time. How do they get in? Mostly officers and, as a favour, not searching visitors too closely. But it does benefit the prison. These days drones too. But since almost all outside drug deals and involvement in crime from prison involves cell phones, it is a mystery why they don't just go back to radios for the officers and jam the signals in the cell blocks.

Why do we cage people? Why not give them nice bedsitting rooms with a tv, a microwave and computer (maybe not internet!) The punishment is to deprive them of freedom, the court does not order extra punishments and deprivations in prison. In Norway they do have nice rooms, and 'club rooms' and are generally treated well and respectfully, even in max security prisons, but they are still prisoners.

Conover covers a lot in his year as a guard. But the book was not revelatory at all, just interesting in a minor way. Perhaps that is because the book is so dated and we've all watched too many documentaries about prisons now.

Notes on Reading So far the book is all about officer training and being new on the job and is all, we did this, we were told that, these are the rules, you are prisoners of the system but not prisoners of the lock-up. Maybe as the gonzo journalist author of this book gets further into his temporary career there will be revelations of prison and insights into the life of the prisoners from the side of the guards. So far there have been none.

[Arista]

This book was an interesting point of view from an actual CO who worked in Sing Sing, a New York Jail still in existence (although a part of it is currently being converted into a museum- http://www.singsingprisonmuseum.org/ )
Anyway, Ted Conover takes us through the training of what it is like to become a CO and informs the reader of how few actually make it. Prison shows, documentaries and books usually portray the POV of prisoners and not often enough of the actual workers.
As an outsider, I can see why many could not survive this job. It is mentally draining and as he puts it "..Prison work was about waiting. The inmates waited for their sentences to run out, and the officers waited for their retirement...it was a life sentence in 8 hour shifts" (Haven't we all felt that way about a job we hate haha)
He even touches upon the topic of prison reform. Some facts given are circa 2000 are: Young black men in California are 5x as likely to go to prison rather than a state university, the number is inmates has tripled in the last 25 years and continues to climb. Instead of reforming prisoners, we just incarcerate them.
At the end, I wondered if employers have a legal right to know the criminal background of an applicant? If you did the crime and paid with your time, why are you punished for the rest of your working age? This leaves people just resorting to more crime in order to survive. What do you think?

[Larry Bassett]

I like books where the author immerses him or herself in a situation and then writes from his or her own experience. Barbara Ehrenreich has done this for several of her books. After my mother was sentenced to jail for civil disobedience, she has a much better understanding of who is in our jails and why. This was knowledge that she might have been able to get from reading a book, but having the experience was so much more powerful. Ted Conover writes as an outsider who chose to spend some time as an insider. The results are fascinating, I think.

Ted Conover wanted to research a story about being a prison guard. He claims they would rather be called corrections officers. But they wouldn’t let him have direct access. So he took the civil service exam and got a job as a corrections officer. He did that for a year. He took a lot of notes. He wrote this book. It is not just about his time at Sing Sing but a lot about the history of the place that has been a prison since 1826.

I am very interested in the issue about how prisoners should be treated. We hear that they are not nice people and that seems to excuse us from treating them with much consideration. Newjack is about how those who are in charge of the daily operation of prison system, the guards, are trained and learn to treat the prisoners. The author admits that some forms of treatment that he would have considered inappropriate when he started come to seem necessary after he had been there a while. What kind of people do guards start out being and what do they become over time as they experience prison life as the keeper?

My own experience being a welfare worker at several times in my work life colors my view of this hardening process. People who are “just doing their job” can treat their fellow human beings quite badly. Take a “normal” person and make him a welfare worker or a prison guard and what do you wind up with? The peer pressure of coworkers in these dehumanizing institutions to treat clients badly is great. In my last welfare job we were told to treat clients as customers! But we were not told that the customer is always right. Is a convicted felon a customer of the penal system? What kind of service do they deserve, both morally and legally? Given the high number of people I was expected to handle as a welfare caseworker, I found it impossible to consistently treat people with human concern and understanding. It was impossible for me not to treat some people badly in the welfare system. Like the corrections officer, my job was to say No quite often.

You didn’t have to be flaying an inmate’s back with a cat-o’-nine-tails to be wounded by the job. That was simply it’s nature, a feature of prison work as enduring as Sing Sing’s cell block design. “In its application the familiarity it causes with suffering destroys in the breast of the officer all sympathetic feeling.”

To do this job well you had to be fearless, know how to talk to people, have thick skin and a high tolerance for stress.

Ted Conover had a degree in anthropology. What he did was apply the anthropological research method of participant observation. What did he discover?

At Attica and Clinton, he said, inmates didn’t even talk to female officers. It was flat-out forbidden.
“And if they do?” I asked, knowing that every jailhouse rule was eventually violated.
Gaines paused and smiled. He was a soft-spoken, gentle-tempered man.
“They get the fucking shit beat out of them,” he said.
The possibility no longer bothered me as it once had.

That's what happened to him. It "no longer bothered me as it once had." A deadened conscience and morality.

There is the mere shade of difference between the guards and the guarded.

The point was that anyone could end up inside. The black officers I knew, especially, seemed to feel this – that the difference between straight life and prison life was a very thin one and that sometimes the decision about which side you were on was not yours to make.

Because of my own experience as a good guy doing bad things, Newjack did not shock me. Why do people become correction officers? For most, the answer is simple: to earn a living when other options do not exist. I first became a welfare worker as a young idealist thinking that I could change the system from within. And I think in several situations I did that. But the system always scoured away any temporary change.

This is a four star book in the style of the muckraking books like The Jungle. Ted Conover was able to shine a little light on the penal system from the point of view of the guards. But he always knew that he was going to escape at the end of a year. It was still oppressive but it is much easier to describe the system than to change it. And he had other choices of what to do with his life. This was just a short side trip.

[Elliot Ratzman]

Prison memoirs by prisoners are plentiful, shocking and tragically predictable; few have narrated the working life of prison guards, doing a “life sentence eight hours at a time.” I read 4/5 of this excellent book in a day—I highly recommend it. The author, Ted Connover, goes through the process of becoming a Corrections Officer in the NY state system. After a few months of hellish basic training, he is thrown “into the deep end” working in Sing Sing prison. Need I say it’s like one big Zimbardo experiment? Conover writes with an anthropologist’s eye, describing the social arrangements, the moral compromises and the banality of prison-guarding evil—including his own. The line between inmate and CO is, of course, blurred—prison traumatizes both. Along with some penology and history, especially in the New York system, we are treated to one unforgettable story, character sketch, wise observation after another. Make sure to get the paperback version which has an indispensible afterwards.

[Mike]

Ted Conover has the crazy idea of working undercover in Sing Sing for a year. This is every bit as scary as it sounds, and without being sensationalistic he shows why being a prison guard is one of the worst jobs imaginable. Conover has compassion for both the prisoners and the guards, without losing his objectivity or coming off as a bleeding heart. In addition to being a great piece of investigative journalism, the book gives you a harrowing account of Sing Sing's history. You discover that, just a hundred years ago, this place made Abu Ghraib look like The Four Seasons.

[Stephanie ~~]

In my experience, Ted Conover will always be One of today's best immersive journalists. To write with devout honesty about difficult topics requires a commitment to see from as close a vantage point as possible.

Ted thought this would be a story. He took the job at Sing Sing Prison and an award winning novel was the result, not because he forced it-- because he earned it, and because he can write the way he does.

Ted never speaks above his reader, and he never tries to come across as the protagonist in his own work. That's not humility, that's accuracy. Rare. Bold. Brilliant.

[Brendan]

Much much more than participant journalism, Conover's ambitious yearlong journey at Sing Sing as a corrections officer (don't call him a prison guard) produced this nonfiction masterpiece. Over the course of NEWJACK (prison slang for officer trainee), the reader sees Conover undergo many transitions: from excited trainee to disillusioned officer, from hardass guard to sympathetic friend of the inmates. Also, playing historian and anthropologist, Conover steps back from his personal experience to offer a timeline of both modern corrections practices and a history of Sing Sing. Although this journey is ultimately unpleasant, this book will change you.

[amanda]

3.5

a bit too much preaching about how cops and COs arent bad. author literally states that it’s not their fault because the job changes them. uhhh okay. he acknowledges a lot of his privilege but yikes. it’s enjoyable however and a product of its time.

[Ryan]

Interesting work of immersion journalism. A reporter works as a 'Newjack' (rookie officer) for a year in Sing Sing prison. This is the result.

I didn't enjoy this as much as I expected. We know the cliches, even some of the lingo from all the prison films (shivs, grab-ass, shittin' down, the box, etc. etc.) Inmate accounts of prison are ten a penny but you hardly ever hear about what the guards go through. I wanted to see prison filtered through the eyes, ears and nervous system of an actual guard.

It doesn't sound like most people's idea of a good job, despite the pension. Suicides, breakdowns, stress and depression are endemic among staff. Few can afford to live near the actual prison due to rising house prices. The officer class is waiting for that long-awaited transfer out and in the meantime are determined to make the lives of the staff below them as miserable as possible. Black and Latino guards are mercilessly baited by the inmates and far worse than white officers.

Some more case studies or anecdotes might have thickened the overall stew. They largely cease after the fifth chapter when the focus starts blurring, never quite regaining the same impact as the earlier material.

[Leftbanker]

Before I read this book, I wrote this short story:
https://shotgunhoney.com/fiction/earl...

I wish that I could have come up with this line from Newjack where he quotes a coworker describing their life as prison guards, “…a life sentence in eight-hour shifts.”

This isn’t a novel. We’ve all read books and seen movies about cooler scenes in prison, but that stuff is fiction. This writer made a serious commitment to a story, like something Zola would have done back in his day. As his bio states, Ted Conover, is a "master of experience-based narrative nonfiction.” I am officially a huge fan of Ted Conover and plan to make my way through his entire bibliography.

The takeaway from this book is that the USA needs to stop putting motherfuckers in prison for bullshit, things like minor drug charges, and non-violent crimes in general. We have other ways of punishing people. Take away their driving privileges. Make them do community work. Force people to take adult education. Because once someone goes to jail, their life is taking a turn for the worse. Period.

Rehabilitation isn't even on the table in the prison system. It's mostly just warehousing young Black men who are much more likely to be arrested and sentenced to prison than Whites.

[Molly]

While volunteering in a maximum security prison, I found I was as nervous around the guards as I was the prisoners. In fact, I did not really care for prison guards at all, but now that I came across this excellent piece of investigative journalism while touring the Eastern State Penitentiary, I am on fire about prison reform and profoundly confused at the complexities involved. Ted Conover spent a year as a corrections officer, and his experiences are told alongside an accessible and interesting history of the American Prison. It should be required reading for every American. There isn't a more expensive and less effective government program, we imprison more people than any other country in the world by far, and our prisons need colossal work and activism to be anything more than a dehumanizing and useless band aid against mounting poverty and recidivism. What is tragic is that conditions in prisons are worse than they were fifty years ago, and it doesn't look great for the future. And on a side note, his experience with prisoners is eerily similar to managing a classroom.

[Петър Стойков]

Книгите и филмите за затворите едно, че почти винаги са от гледната точка на затворниците и второ, са пословично далече от реалните условия и отношения между хората (и особено между затворниците и надзирателите) вътре - до степен да нямат нищо общо с нея.

Всеки път обаче, когато чета книга, писана от човек, който наистина е бил вътре (от която и да е страна на решетките), се удивлявам на сходствата на всички затвори по света. Независимо дали се намират в САЩ, в Бразилия, във Великобритания или в България, навсякъде затворите се борят непрестанно с недостатъчния бюджет, с недостатъчно персонал и проблемите в набирането му, с идеите на администрацията и политиците относно това какви трябва да са отношенията между хората в затвора (което включва всичката гняс, свързана с политическа коректност, употреба на сила, дисциплина и т.н.).

"Новобранец" не е лоша книга, ако я приемем според както подсказва заглавието - като погледът на един журналист, изкарал "под прикритие" една година в ролята на надзирател в най-известния (и един от най-трудните) затвор в САЩ - Синг Синг. Определено е истина твърдението на по-старите надзиратели, описано в книгата: че за да станеш наистина надзирател, ти трябват минимум 4 години служба. Преди това си новобранец и нищо не разбираш - нито от работата, нито от това какъв човек си.

От такава позиция авторът е описал каквото е видял, па макар и ограничено от малкия му опит.

[Phillip]

I picked up this book since I have been incredibly interested in prisons for about a year now. It started with watching the first season of Orange is the New Black about a year ago. I followed it up by watching a bunch of prison documentaries on NetFlix. After exhausting that medium I decided to look for a book, and found this on a top ten list. After I picked it up I realized I actually read another book, Coyotes, by the same author as a choice in 11th grade English Class. I remember enjoying that one which increased my expectations for this one.

The book is the account of a year the author spent as a prison guard at Sing Sing. He was turned away in his attempts to interview prison guards or do any investigative journalism, so he decided the best way to find out the truth was to go undercover. I find the premise of the book in and of itself a little bit shaky. Obviously the author brings his own perspective into becoming a prison guard, but it isn't exactly out of the ordinary. This is reiterated in his training class where most of his fellow trainees were simply down on their luck and looking for a decent paying job. These people didn't seem particularly remarkable for choosing this profession in any way. My other issue with the premise is that it only lasts a year. This influences his ability to cope with the situation so he doesn't experience the limited options and outlook of those who actually have this as their actual job. The author describes this in one of the chapter about how this affects his family.

Unfortunately, some of the details about being a prison guard are not particularly interesting. A lot of the training and the more technical explanations of how the prison works I found somewhat lacking. This wan't because they were poorly written, it just isn't particularly exciting. The most exciting part about prison is, well, the prisoners. Unfortunately due to his changing assignments and the large amount he encounters, there are only a few of them that he knows well enough to get into any amount of detail.

I also found the structure of the chapters to be somewhat frustrating. Since most of them are a collection of anecdotes, he often tries to put them within the frame of a larger story. Unfortunately the larger story isn't worthy of the status. One of them was actually a time he was walking down the corridor and another guard told a story. I would have preferred the stories and charicatures to be presented more thematically instead of the confusing way he did it.

All that said, he does provide an acute level of insight into the prison, and the snapshots of some of the prisoners are memorable. My favorite chapter was actually the one he wrote that did not have anything to do with his experience, but was a history of Sing Sing. It also made me wish he was allowed to do interviews and research instead of engaging on this undercover operation.

[Jim]

This is an interesting book about life inside prison by one of America's most innovative authors/journalists.

Conover made numerous requests of corrections authorities to visit Sing Sing, one of New York state's (and America's) most notorious prisons. He was denied time and time again any opportunity to visit, or interview inmates, officers, etc. Conover, unlike most writers, who would have given up and picked a new topic, applies for admission to New York's correctional officer training academy and is selected to go through the two-month training. He is eventually assigned to Sing Sing.

The book covers the nearly one year that Conover served as a corrections officer at Sing Sing.

It' s an honest look at incarceration in America, our nation's burgeoning prison-industrial complex, and how life in a prison, whether an inmate, or as an employees, alters your perception, and who you are as a person.

I'll share with you that I once worked at a medium-security prison in Westville, Indiana for four years, as a med-tech, and it changed how I view prisons. Sadly, we keep building them, locking people up needlessly, and in many parts of the country, prison-building constitutes economic development.

A first rate read

[Ensiform]

The author, an anthropologist journalist, went through basic training and became a corrections officer in Sing Sing for a year. The usually secret world he uncovers – of brutality (almost entirely on the inmates’ side), of facing danger daily, of learning to enforce some rules and let others slide – is fascinating. He also makes some fine discoveries about the criminal mind; while he does get chummy with some inmates, by the end, he finds himself both invigorated and repelled by the violence all around him. It seeps into his home life, but he also feels exhilarated when there’s a cell extraction, for example. And he begins to lose his liberal idealism: “beating the shit” out of recalcitrant inmate doesn’t bother him as it once did.

Other than one long, misplaced chapter on Sing Sing history and two of its influential wardens (semi-interesting stuff, but fit for a different book or article), this is an engrossing feat of undercover journalism into a shadowy world. America’s penology system needs a clear-eyed and sympathetic look, and Conover gives some good indications that the animals might be taking over the zoo.

[Darcia Helle]

I want to start by saying I have immense respect for Ted Conover. When our prison system denied his request to shadow a corrections officer recruit, he sidestepped the system and applied for the position himself. His commitment to the job, in order to bring us the story, is commendable.

Newjack is an honest, straightforward look at life inside a prison from the viewpoint of a corrections officer. While I read a lot on this topic, most books come from the inmate's perspective. I was shocked to learn how little training these men receive. They go from a short 7 weeks at school straight to prison work, having had absolutely no prior contact or training directly with inmates. These men and women who risk their lives each day are woefully unprepared for the reality inside those walls. This book is a scary, sad, sometimes funny look at that reality.

I've long believed our prison system is a mess and only reinforces negative behavior. If you doubt that at all, you need to read this book.

[Emily Goenner Munson]

Interesting, but I have a prison connection at the moment which made it real and relevant. Society's prison culture is a topic, though, that should be of interest to more people due to its size, growth, and the destruction it causes to families of inmates and guards. Conover is engaging, astute, and colorfully describes many of the characters he meets, inmates and other guards alike.

[Tracey S]

In the early 1990s anthropologist and journalist Ted Conover applied for access to visit Sing Sing maximum security prison in order to write about it and was turned down. Undeterred, Conover at once applied to become a Corrections Officer as a loophole to gain access, and in 1997 he finally got his chance to be a Newjack (a trainee CO).
He begins by relating his experience throughout the 7 week training camp where recruits had to go through all sorts of rituals, including being exposed to tear gas, in order to know what it will be like for the prisoners on their watch if they had to resort to force.
When it comes to actually starting his new job, Conover is frank about his fear and anticipation about working in one of America's most famous and largest prisons, about perhaps not being able to do the job, about the inmates, about his fellow officers.
The reader gets a definite sense that the author is appealing to those like himself who cannot see the logic and purpose in imprisoning more and more people. His belief is that a Corrections Officer is a misnomer, as the guards are in no way responsible for rehabilitation of the criminals they look after, and are not expected to try to interact with them. State money is not being spent in the right places, is another of his strong arguments.
I rate this book a 4.5- the subject matter is absolutely fascinating, and the author is sympathetic and at the same time at the correct amount of distance from the narration. I think the books suffers a tiny bit from being dated, although there is a very quick afterword written in 2011 (the book was published in 2001).

[Nick]

Newjack (noun): A novice officer.

Journalist Ted Conover set out to understand the corrections system, focusing his research on New York State's long history of sprawling prison complexes and prolific incarceration rates. When he was denied the opportunity to shadow a recruit at the New York State Corrections Academy, he became a recruit himself and spent nearly a year as a Corrections Officer (C.O.) at the storied Sing Sing prison in Westchester, New York.

Sing Sing was built nearly two centuries ago in 1826, and it is a prison built by prisoners. It was prisoners who quaried the marble for the walls that would one day confine them. Sing Sing is the second oldest and second largest prison in the state, and nearly three out of every four of its ~2,400 inmates are violent felons.

"The truth of it is that we are warehousers of human beings," and today's prison, seemingly above all else, is one large, concrete and iron storage unit.

Newjacks are caught in this ironically mirrored and messy middle. One the one hand, it is so evident how new they are, how little they know that they struggle to build relationships or earn the respect of inmates. One the other, it is so evident how new they are, how little they know that they struggle to build relationships or earn the respect of their fellow officers.

What Conover describes so straightforwardly is a job that amounts to "a life sentence in eight-hour shifts," a burden that's impossible to "leave at the gate" (i.e., not bring the stress of the job home).

America is in an incarceration crisis that's impossible to not also describe as a moral crisis. Even while crime rates fall, more and more people are getting locked up - largely driven by mandatory sentencing for nonviolent drug offenses. The number of Americans behind bars has several times multipled since the 1980s such that, by 2000, 1 in every 140 residents in America have been incarcerated. In that same timeframe, the number of corrections officers has skyrocketed 400% from approximately 60,000 to a staggering 240,000.

While our prison system proliferates, our healthcare and education systems deteriorate. There's a powerful moment in Newjack where it is said that the growth of correctional development is so vast that we're already planning for the prisons we'll need to build over the coming 15 years to continue meeting demand. With so many of today's incarcerated being between the ages of 20-35, that means we are already planning for the incarceration of today's youth. Conover poignantly argues that we must "stop planning for the incarceration needs of today's children, and instead begin reducing their poverty and increasing their opportunity."

An engaging read, a realistic portrayal, and a powerful argument for reform.

3.75 out of 5

[Rob1]

A well documented if slightly dated look inside America's prison system.

[Eva]

Solidly interesting. Some kindle highlights:

In the 1990s, while Wall Street was booming, one out of three black men between the ages of twenty and twenty-nine was either behind bars or on probation or parole. Young black men in California are now five times as likely to go to prison as to a state university. - location 413


Fifty of the state’s seventy-one prisons were built in the last twenty-five years, a period in which the number of inmates has increased nearly sixfold, from 12,500 to over 70,000, - location 531


As a result of an inmate takeover of the Coxsackie Special Housing Unit (SHU) in 1988, Council 82 had initiated hostage insurance—a payment of half a year’s salary to any member held hostage for more than eight hours. (“If they’re gonna release you after seven and a half,” a Council 82 rep had quipped to us, “tell ’em to go make a pot of coffee.”) - location 1043


Criminals used to travel to Sing Sing by boat from New York City “up the river” to “the big house,” some thirty miles north. That’s how both phrases entered our language. - location 1137


We broke for lunch, and afterward, we were each issued a baton. Down the row from me, someone noticed that his had dried blood on it. - location 1206


Weight lifting was also popular, and when I was new at Sing Sing, it was intimidating to be faced with the huge, muscle-bound inmates who took it seriously. But soon I noticed that these purposeful, self-disciplined inmates were almost never the ones who gave us problems, and I came to agree with the opinion, generally held among officers, that the weights and machines were valuable. The only complaint I ever heard from officers was that inmates’ weight equipment was much better than what was provided to officers in the small weight room in the Administration Building. - location 2400


Another memo, four years old, described the Family Reunion Program, probably soon after its inauguration. Entrance to the family-visit trailers was through the sally port at Wallpost 15, where I would work later. Each unit had an outdoor grill and picnic table, and they shared a swing set; inside, I was told, there was a television, a kitchen, and separate sleeping areas for kids and adults. Married inmates on good behavior were eligible to stay there every few months. The Felon Reproduction Program, some officers called it. - location 3224


“Where were you stabbed?” Toussaint lifted up his T-shirt and showed the cut in his back. He would have gotten a “big stick” in his side, too, he said, had it not been for his protective vest of magazines. “What magazines did you use?” asked Anderson, the female CO who supervised the barbershop downstairs. “Ebony and Life,” said Toussaint, smiling. - location 3374


In 1901, in fact, in order to more fully disassociate itself from the infamous prison, the town changed its name to Ossining. - location 3696


The death of Druse gave new life to efforts to reform New York’s capital punishment, and in 1888 the legislature, hoping to burnish the reputation of the Empire State, established “electric execution” (electrocution was not in common usage yet) as the state’s official method. - location 3726


Thomas Mott Osborne’s inspirational tenure as warden of Sing Sing was typical only insofar as it was short. Until the 1950s, when it became a civil service post, the job was a political appointment, often bestowed on men who knew nothing whatsoever about running a prison. “The quickest way to get out of Sing Sing is to come in as warden” was a popular joke. Thirty-one Sing Sing wardens had lasted only little over a year; they included a steamfitter, a coal dealer, a horseman, a postmaster, a customs revenue collector, a millionaire and philanthropist, and “assorted ward-heelers.” - location 3977

[Zane]

The premise of this book is that the author Ted Conover got a job as a ‘corrections officer’ in Sing Sing to see what it was like to be a prison guard. Seeing as how he looks ‘not tough’ and was used to hanging out with the high society of New York (not the magazine), he comes off pretty whiny sometimes, but it is clear that it is a pretty terrible job, in part due to the stress and psychological requirements necessary to telling people what to do all the time and, in turn, being resented for it.

As we all should know by now, prisons do not do what they were created to do (reform people to act a certain way in society). From the book, one gets the impression that most prison guards (‘corrections officers’) in some way recognize this, but have to act within the rules to maintain their authority or suffer the possibility of violent repercussions (from the people who they are talking down to all day) or being fired. Conover describes this task as one of running a micro-totalitarian state (which includes not letting people shower just any time, not letting people have too many waffles on waffle day, not letting people make elaborate antennas to pick up radio signals, dehumanization, etc.). The sum of this micro-management is alienation of both guards and prisoners.

In this book, and another that I have been reading that is a collection called ‘20th century prison writings’, there is discussion of a reform in the 1910s that took place under T.M. Osborne, who took on this alienation from self-determination. As warden, Osborne spent a week as a prisoner to see what that life was like and from there decided the way to get prisoners to learn to make desirable decisions was not to stop them from making any decisions, but by granting them responsibilities and access to decision-making structures. The movement was somewhat successful, but, of course, looked down upon by ‘tough on crime’ statesmen of the day as being too lax. In the end, the alternative system’s power fell into the hands of gangs and prisoner power brokers, and it was dismantled. The idea was taken up again, however, by a later warden who was a former CO. He critiqued Osborne’s ideas as giving too much responsibility too fast. I guess it was a bit naïve to expect a population, the majority of whom had been told what to do 24 hours a day for many years and were conditioned to get what they wanted through anti-social behavior and alternative political networks (gangs) would be able to transition into a democratic system of power without first becoming subjects of direct democracy. The idea of this conditioning could be similarly applied to non-prison society (learning to defer one’s authority to overseers in school and at work).

All-in-all, the book is really good for people like me who have trouble imagining how and why corrections officers can do their job, or how even some liberal from NYC who believes prisons don’t work and generally walks a middle ground between empathizing with prisoners and sympathizing with guards becomes blood-thirsty in some situations and at times gains sadistic pleasure through the power of micro-management, which is important if we want to speak seriously about prison reform and abolition.

[Liralen]

Here's one for the 'jobs I never knew I didn't want' list (previous entries include vet and farmer). I suppose this could be called stunt journalism -- unable to gain access to the Sing Sing corrections system as a reporter, Conover simply became a corrections officer himself -- but if so, it is stunt journalism at its best.

Conover had originally hoped only to shadow a recruit going through the training process, and when he submitted his own application to be a CO, that was his end goal -- get through the training process, get out, and write about it. Instead he stuck it out for a year, learning not only about training but also about the inner workings of Sing Sing.

He does not paint a pretty picture. Make no mistake -- he's not advocating for the inmates here; this isn't an exposé of flaws or abuses in the system. But neither is it an endorsement of the system, or of the ways inmates are treated. He gets to know other officers -- those who use and abuse their power and those who earn some modicum of respect from their charges. He gets to know some inmates as well, to one degree or another. One of the most fascinating things to me is how little curiosity he sees in the other COs: It serves him well, as rarely is his cover story questioned, but they are often of little use when his own curiosity is piqued. Some of the COs and superiors strike him as creative, competent, flexible where needed; some don't seem destined to rise (I believe he describes one lieutenant as semiliterate).

The Powers That Be were not, unsurprisingly, happy with the news that Conover had written about his time in Sing Sing, and it's true, he does not paint a particularly flattering picture. There are flaws in the prison system as a whole and Sing Sing more particularly, and he doesn't hesitate to point them out. Beyond that, it's a grim, grey place from where Conover stands, and he's not interested in flattery of any of his subjects. But -- as far as my limited knowledge of prisons goes -- he seems pretty damn determined to be balanced, and outside a slog or two (did not need all that prison history packed into one chapter) it makes for fascinating reading.

[Andrew Benedict-Nelson]

The blurb from Tracy Kidder on the back of this book compares it with the journalism of Orwell (Homage to Catalonia, Down and Out in Paris and London, Burmese Days) and I have to agree.

While no one could duplicate Orwell's way of subtly imbuing every moment of a narrative with political meaning, Newjack has a different kind of appeal: Conover, perhaps because of the ordeal he endured, allows himself to become much more vulnerable in his text than old Eric Blair ever did. It might be that vulnerability that gave Conover the sensitivity to observe the images that at times make Newjack transcendent: the father who after decades of lockup encounters his son in the inmate showers, the prisoner who keeps a spider for a pet, the Latino man who solicited a cellmate to melt plastic from stolen silverware and tatoo a passage from The Diary of Anne Frank onto his back in Spanish. Then there is the unforgettable spectacle of Sing Sing's B-block on a New Year's Eve -- I won't give that one away.

Newjack does have a few limitations. Prison life is by nature mind-numblingly bureaucratic, and that tone occasionally (and unavoidably) creeps into the text as Conover attempts to describe what he actually did as a corrections officer every day. But fortunately, the two missing elements I felt the book most needed -- a map of Sing Sing and a reflection on Conover's experience once he was away from the "scrap heap" -- are included in the latest edition. Conover also offers some recommendations on how we might improve America's penitentiary systems, though a decade on it seems like we have heeded few if any of them (plus built Gitmo to boot).

[Mike]

'Newjack' is a commendable book and achievement, as the author, Ten Conover, spent a year working in Sing Sing prison as a correction officer and meticulously recorded his experience.

He exposes the hypocrisy of correction officer training which stresses strict adherence to rules versus the real life mishmash of daily rule following on the job. He dispels some common myths about prison guards (they aren’t all terrible inflictors of random violence, as seen in movies) and prisoners (they aren’t all mindless, sociopathic thugs). He also explores the personal impact of working in such a stressful environment, where a mistake can lead to violence or even death for a corrections officer or an inmate.

The problem is that the narrative breaks down in the back half of the book and many sections seem superfluous. Did we need a full chapter devoted to the history of Sing Sing? This is logical and relevant to the topic at hand – I just found it less interesting when compared to some of the better personal stories about prison life. His on the job experiences were unique, while a Wikipedia page probably could have provided some of the history. Unfortunately, not all the personal tidbits are compelling and at times I felt like I was listening to somebody at a party explaining in too much routine detail about their job that day. The book thrives in the earlier chapters, when Conover stirs emotions when he deals with aggressive instructors in trialing or unpredictable inmates on the job.

While I commend the author on the thorough reportage, I guess I expected more from a book that is so highly honored (Pulitzer Price finalist, etc.).

[Aaron]

I got this book out of the library after hearing what must have been an old interview on Fresh Air with Ted Conover (the book was published in 2000). Some disapproved of his methods. He wanted to learn about being a prison guard, but no one in the DOCS system would let him shadow a new recruit. So he signed up himself and did all the testing and training and then worked as a CO at Sing Sing for a year.

The result is a really good book. No huge revelations, but a good thorough interesting if rather small-scale look at the work of guards in a prison. He ends the book with some of the usual pleas that seem to come from nearly every human being who takes a look at our Prison Idustrial Complex - stop putting drug offenders in with violent offenders, get rid of mandatory sentences for drug offences, make more of an effort to educate prisoners (and guards), etc.

Glad I read it. Still depressed about the prison economy.

[Vanessa]

"These were the guys, the source of my pain, the source of their own pain, the source of their victims' and of their families' pain. My first few days, they had seemed like one big green-clad undifferentiated mass. Now, of course, they all had faces to me."

a book has never given me so much secondhand stress

reread 2026. Yeah, still holds up. A little dry in spots, a little oddly dense-feeling because of the lack of chronological structure or much structure at all, but it's a unique, fascinating account that is beyond comparison.

I read this throughout the month of starting a new job and good God. Made me feel Calm and Grateful for employees who follow the rules

If they are not going to be put to death, the monstrous must be warehoused. Trying to extinguish the spark of the rest--the merely incorrigible, those holding on to civilization by a thread--itself feels like a monstrosity.

[Badly Drawn Girl]

A gripping page turner that reads like a novel, Newjack is a book that gives outsiders a glimpse of the realities of prison. Ted Conover goes undercover because he isn't granted any access to information as a journalist. But he doesn't approach it as an undercover stint, he goes through correctional officer training with the intention of becoming a CO. The reader gets to experience it all alongside him... training, first day jitters, fears, biases, friendships, and violence. I have read a lot of books about prison, usually written from the prisoner's perspective but this book was the first I'd read that addressed the other side of bars. Ted Conover does an amazing job at presenting more than one side of the story. I came out of it with a new respect for the men and women who work in the prisons.

[Jessica]

I found Conover's story completely fascinating, as would just about anyone with an opinion about the American justice system and its prisons. Sing Sing is a particularly excellent place for him to immerse himself in this world as it's a 150+ year fixture of corrections in this country, as well as a crossroads between the clearly very different worlds of Rikers Island and prisons farther upstate.

While the history and Conover's efforts to learn the job captured my attention initially, what I can't stop thinking about is how the very system of incarceration influences the jailers as much as it does the jailed. Conover's discussion of the psychological impact of corrections work will stick with me for a long time, and I hope this issue gets more attention in the larger discussion about prison reform.

[Victoria Weinstein]

Preachers, start your highlighters. This is a powerful book about how guarding prisoners degrades the souls of those working in the system just as surely as it degrades the souls of those in lock-up.