Newjack: Guarding Sing Sing

ISBN: 0375726624
ISBN 13: 9780375726620
By: Ted Conover

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About this book

Acclaimed journalist Ted Conover sets a new standard for bold, in-depth reporting in this 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. As sobering as it is suspenseful, Newjack is an indispensable contribution to the urgent debate about our country’s criminal justice system, and a consistently fascinating read.

Reader's Thoughts


I was really looking forward to reading this book and was not disappointed. Conover is known as one of the leaders of the "New New Journalism" school -- "contemporary American literature for reportorially based, narrative-driven long form nonfiction". Conover's MO is immersing himself as a participant in his topic to see what the life is really like, then writing about it. For NEWJACK, he took a job for a year as a guard at Sing Sing, the famous New York maximum security prison. The result is a study of the American penal system unlike any other. What is particularly great about Conover's approach is that, as a participant, he is a character in the telling and is our stand-in on questions of morality and individual responsibility in a tragically flawed, yet tragically necessary, part of our society. My curiosity in the real life hiding behind the Hollywood-ized prison experience can be sated because Conover went somewhere I don't believe I could ever go myself. And the questions he asks of himself about such things as justified use of force (ie, violence) and fraternization with hardened criminals are the very questions I might ponder in his situation. The answers he provides are sometimes surprising, sometimes humorous and always thought-provoking.

G.d. Brennan

Walter Cronkite once said that the citizens of a country have a right to know what's being done in their name. It's a simple enough premise: public institutions, spending public money, should be subject to public scrutiny. And yet, the nation's prisons and jails remain practically invisible to the public eye, thanks to both their media-shy temperament and a relatively incurious media. Newspapers and television may flock to chronicle shocking crimes and sensational trials, but when the sentences have been handed down and the headlines are fading, the public mentality seems to be "out of sight, out of mind."Journalist Ted Conover sought to redress this problem, to understand the corrections system in New York State and, in particular, the corrections officers who, on behalf of the public, guard those deemed unfit for society. Towards that end, he wanted to follow a rookie C.O. through training and into an initial posting, but was repeatedly denied permission to do so. Rebuffed by the powers-that-be, stymied by the system, he settled on an even better and more original solution: to become that rookie C.O. himself.Many journalists aspire to be (or pretend to be) completely objective--dispassionate chroniclers of the world, separate from the people and situations they write about. The brilliance of Conover's book is that he took a completely opposite tack, enmeshing himself in the system rather than trying to observe it at arm's length. And in doing so, he has created an excellent, compelling, and thoroughly informative book, one that dismantles many stereotypes about prisons and guards, stripping away the lumpy old layers of paint and showing the true shape and color of things.Many of his most insightful observations deal with a very poorly understood subject--the effects of incarceration on the guards. At the outset of his experiences, Conover wonders whether guards truly are the brutal people depicted so often in prison movies and, if so, whether they are drawn to the work because they are insensitive, mean people or whether they become that way because of the work. By the end of his time guarding Sing Sing, he seems convinced that the latter is often the case, that warehousing people can end up dehumanizing both the people being warehoused and the people doing the warehousing. The stress and strain of prison, it seems, seeps into the lives of C.O.s, resulting in higher rates of alcoholism and divorce. (Those who pick this book up expecting an overly-sensitive, "Cool Hand Luke"-ish rant about cruel C.O.s and maltreated prisoners will find themselves pleasantly surprised by the author's fairness and empathy towards his fellow guards.)Prison sex, too, appears far differently on the inside than it does in popular culture. While prison rape is a staple of movies and shows about incarceration ("The Shawshank Redemption", "Oz"), Conover concludes that most prison sex is, in fact, consensual. Such observations may seem like voyeurism, but they are not; given the lower availability of condoms, the higher rates of infection for sexually transmitted diseases (particularly HIV) and the fact that many of these men will eventually leave prison (possibly to rejoin thier families), prison sex is a factor that fundamentally alters the incarceration equation.Despite its overall excellence and its willingness to take on such edgy topics, the book isn't a completely thorough or representative picture of New York State's corrections system. The author readily admits that Sing Sing is an atypical prison, with a larger percentage of minority guards and unseasoned officers than the upstate facilities; it would have been interesting if he'd been willing or able to spend longer in the system and get a better look at those institutions.Still, this complaint is insignificant when compared with the book's overall virtues. "Newjack" is a great public service, a must-read for anyone seeking to understand the consequences of the nation's get-tough-on-crime mentality. While many people affect a cavalier don't-do-the-crime-if-you-can't-do-the-time air, Conover's book shows that this is a very myopic attitude--prisoners will do the time, and they will emerge, and the experiences they face on the inside will help determine whether they will do the crime again or instead find a place in society. Given that fact, society should try to better understand what life is like for them--and for the guards who do the public's thankless bidding.

Chris Birdy

Newjack: Guarding Sing Sing by Ted Conover was an informative book that gave a brief look into the life of a corrections officer. Mr Conover took the reader from his first day of training through his last day on the job - one year. The book was well-written. My only problem with it was the second half of the book was loaded with history on incarcerations and punishment. The information was good; however it seemed to all be packed into the second half as filler when he had nothing more interesting to say about his job at hand.


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


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.


As someone who works in corrections, I thought it was gutsy the way Conover got the background to write his book. He actually took the time and energy to apply as a corrections officer and got the job! For someone that doesn't know anything about corrections, he takes you in this sub-culture from the beginning and takes the reader though the steps necessary to become a corrections officer. From there, the reader is taken inside the prison, with its' many officers, nuances of prison life and the metamorphosis from civilian, to CO, guarding some of the most dangerous people society keeps locked up. The mystic behind Sing Sing is unveiled as is the daily workings of an "average" prison guard...a book that should be explored! Good job Conover!


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.


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.

J.A. Callan

Ever wonder what life is like for the average prison guard (or Corrections Officer, to be PC)? Well, this is the book for you, then. Conover displays guts of steel in his undertaking of this project - masquerading as a corrections officer in order to gain the experience of what life is like for a prison officer in New York's Sing Sing Prison (The only prison in the world, I learned, which has a commuter track running through it!)The book delves into the lives of officers and inmates. The officers are essentially serving life sentences in eight hour shifts, Conover poignantly tells us. Entangled in a system which teaches them behaviour and protocol which sounds great in practice but once you pass through the gates and onto the Block or the yard it's an entirely different story altogether.Conover also presents us with a fascinating insight into the history of Sing Sing prison - which is known somewhat in popular culture today as being a mobster's jail. Conover is anguished by his experiences: the stress and abuse from a thankless job, and by some inmates who may not be incarcerated had they been born into a different part of the world.


'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.).

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).

Emily Goenner

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.


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.

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.

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