Newjack: Teaching in a Failing Middle School

(Harvard Educational Review, Volume 74, Number 3, Fall 2004)


Last year, before I had even thought of becoming a teacher in New York, I read the book Newjack: Guarding Sing Sing, by journalist Ted Conover (2001). Having been refused a request to shadow a prison officer recruit for a writing piece, Conover applied to the New York State Corrections Academy and became a recruit himself. The book is an account of the year he spent as a guard in the famous New York prison. In candid and compassionate terms, Conover describes the training and daily life of a first-year corrections officer working in a facility renowned both for its history and its unruliness. The book description on the back cover of the paperback reads:

Through his insights into the harsh culture of prison, the grueling and demeaning working conditions of the officers, and the unexpected ways the job encroaches on his own family life, we begin to see how our burgeoning prison system brutalizes everyone connected with it.

In June 2003, I finished my first year as a middle school teacher in New York City. I am part of the New York City Teaching Fellows, an alternative certification program that seeks to fill teacher shortages by training professionals and college graduates from other fields to be educators. Fellows receive three months of intensive summer training and then begin teaching in “hard-to-staff” schools, many of whose credentials are in jeopardy due to low test scores. I teach sixth grade at a public middle school in Bushwick, a neighborhood in Brooklyn. My year has been tough, and filled with many of the complaints shared by my colleagues in the program — poor student behavior and academic performance, insufficient administrative support, and sheer exhaustion. One reaction, however, has been completely unexpected. I have been both intrigued and appalled by how often I have thought of Newjack since beginning my job. Many of my own experiences led me to recall Conover’s memoir, comparing my first year as a New York Department of Education teacher to his as a Department of Correctional Services officer. I have concluded that my school shares many — too many — similarities with the prison where Conover spent twelve months. From their physical structures to the human relations within, to the legacy of failure in both institutions, the parallels between Sing Sing and our school are clear and ominous.

I will discuss these parallels, using Conover’s book as a foundation. My aim is not to say that our school is just like a prison. Rather, I hope to make clear that, because the school replicates many of the elements and dynamics of a prison, it makes its motto, “Raise Our Expectations to Cross the Bridge to Success,” all the more unlikely to be fulfilled.


The Physical Environment

I started at the school on a hot July day, the first day of summer school. Having received my assignment at the district office, I walked the ten blocks from there to the school. The school, which is in a neighborhood that is visibly poor but relatively well kept, appears stately at first glance. Its rectangular, yellow brick structure reminded me of my high school in Boston, also built in the early twentieth century. A fence encircles the grounds, and there is even a bit of enclosed greenery in the front, although a sheet of asphalt covers the back. To enter, you must sign in with the unarmed school safety officer (one of four on duty) and proceed upstairs to the main hallway. My immediate impression of the school’s interior was that it was a dreary place, not at all the warm, inviting place that a school should be. There is no natural light in the corridors, and their hard, dull surfaces give the place an institutional feel. The light that does enter the building is heavily filtered by the sturdy metal grates that cover each window. These metal grates, as well as the cage-like structures that “fall-proof” the stairwells, were what first caused me to think of a prison. Walking through the halls, peering into different rooms, I saw that some were orderly and some were in varying stages of disrepair — several were strewn with trash, and one room appeared to have been flooded. Few rooms were air conditioned, and the oppressive summer heat did not make the prospect of student teaching summer school any more appealing. As I walked to my assigned room, I considered the fact that I would spend the next two years of my life working in this building, and the thought did not cheer me.


The Social Environment

In his book The Tipping Point, Malcolm Gladwell (2000) discusses what he calls “the power of context.” Reviewing various experiments on the circumstances in which schoolchildren cheat on tests (as well as the famous Stanford Prison Experiment where students took the roles of jailers and prisoners), Gladwell concludes that environmental conditions such as order, chaos, tranquility, or disrepair significantly determine how people behave. For example, turnstile jumping is more common in a dirty, dangerous subway station than a clean, safe one. Children who misbehave in a rowdy classroom are less likely to do so in a well-managed one. This means that “children are powerfully shaped by their external environment, [and] that the features of our immediate social and physical world . . . play a huge role in shaping who we are and how we act” (p. 168). In other words, physical and social environments that promote good behavior are more likely to result in good behavior. Gladwell explains, “In ways that we don’t necessarily appreciate, our inner states are the result of our outer circumstances” (p. 152).

As indicated above, our school’s physical environment bears resemblance to a prison-like structure, and the social behavior inside all too often reflects that similarity. Below I will focus on how the social environment of my school, namely, interactions between staff and students, affects the behavior of both and reinforces the similarity to the interpersonal dynamics found in Conover’s prison.



In order to occupy a position of authority, one must assume that authority. Just as Conover (2001) learned that wearing a uniform and a badge does not necessarily engender respect and obedience, I also quickly found that holding the position of teacher in a classroom does not automatically earn me respect. Both the corrections officer and the teacher must assume their authority; in other words, they must make clear that they are in charge through word and deed. Conover describes the importance of control in this process: “Many judged themselves and their peers by the degree of control they were able to maintain over inmates” (p. 31). “Officers critiqued the permissiveness they perceived in each other more than any other quality” (p. 90). The same circumstances exist among the faculty of our school. Those who can control their classes are accorded the most respect. Ms. X and Ms. Y are lauded for their superior control, and many — myself included — have spoken of their skills in wistful terms as we wonder just how they do it. However, teachers who have no control are viewed with either pity or scorn. Control is viewed as the sine qua non of teaching at our school, to the extent that even a teacher who is unsuccessful as an educator can be valued solely for his or her ability to make students comply with instructions. For example, the teacher of one of the most notorious classes, a group of eighth graders with academic and behavior problems, failed a state teacher exam, but she was nevertheless viewed as an essential teacher because the consensus was that she was the only one who could control those students.

One quickly learns that the school, for the most part, leaves the issue of control to the teachers. Discipline, except for the most egregious violations (e.g., assaults that cause injury), is mainly the classroom teacher’s province. While school discipline guidelines do exist, these are followed inconsistently. Conover speaks of the effort expended to “become savvy as to which rules were commonly ignored” (2001, p. 107), an unsanctioned but necessary part of fitting into the culture of the institution. I remember that I spent a lot of time during my first months trying to discipline students for infractions of these guidelines — being out of uniform, using bad language — that in retrospect seem inconsequential to the point of being comic. I gradually learned to conserve my disciplinary ammunition for the “big stuff,” like fighting or other serious disruptions.


Us vs. Them

While there are as many routes to achieving control as there are teachers, some prevalent themes are apparent. Conover observes that prison “is actually a world of two sides . . . the ‘us’ and the ‘them’” (2001, p. 18). This separation creates a palpable adversarial dynamic in which each side expresses contempt for the other. He recalls officers who dehumanize their charges, referring to them in derogatory terms. Conover reasons that regarding inmates as savages is a coping mechanism for the officers: “If a savage dissed you, what did it matter? And if a savage got hurt (particularly due to an error on your part), who cared?” (p. 87). Like Conover, I remember being repulsed by colleagues who referred to their students as “bitches,” “assholes,” and “animals,” to name but a few epithets. But given the oppositional atmosphere of our school, this same dehumanization strategy is perhaps a natural, if extremely distressing, reaction to the circumstances: If a disruptive student insults you, what does it matter? After all, he or she is just an “asshole.” And if your students do not learn, well, it is because they are “animals.” This logic does not make the place any more pleasant and it wreaks havoc on the educational mission, but for some it makes the job more bearable.

The “us vs. them” dynamic frequently manifests itself on a quotidian level. Every challenge by a student is a test for the teacher, who must constantly reassert authority in order to maintain control. Conover recounts a seemingly minor dispute with an inmate over a radio antenna that erupted into a fierce exchange, which echoes the daily arguments I have with students over such trivial matters as borrowing pencils, where to sit, or going to the bathroom: “In prison, unlike the outside world, power and authority were at stake in nearly every transaction” (2001, p. 98). Unfortunately, our school seems to be “unlike the outside world” as well. Challenges to authority are frequent, as are refusals to comply.

Conover writes of the fear of a confrontation in which an inmate refuses to back down from a relatively minor infraction: “But what were you to do in such a situation? Write the inmate a ticket for disobeying a direct order? Walk away and lose face?” (2001, p. 58). I too am afraid of confrontation. Rather than subsiding as I gained more experience, this fear grew over the course of my first year, because it became clear to me that little in the way of substantive consequences exist for all but the most disruptive behavior. Writing tickets, or in our school “referrals,” is futile, and I largely stopped issuing them. Discipline, apart from a short-lived and anemic lunch detention program for tardy students, seems reserved for infractions that would be better termed felonies. The suspensions that I am aware of are due to injurious physical assaults on teachers and students, several of whom have gone to the hospital for treatment. By way of comparison, what would be considered suspension-worthy in many other schools — for instance, loudly telling the principal to “shut the fuck up” on the first day of school — tends to conclude with the loss of face, not for the offender but for the victim. In this case, the principal shook his head, told the student not to speak to him like that, and walked away. In order to avoid the potential loss of face, many teachers resort to bluster and verbal aggression, as if to overpower and suppress any resistance from their students. Some teachers seek to develop the “command” voices favored by law enforcement to obtain immediate compliance; others simply yell at the top of their lungs. This very much unnerved me when I began teaching; now I barely pause when I hear the savage adult bellowing that constantly echoes down the halls. While screaming is of dubious pedagogical value, many of its practitioners would agree with the corrections officer who, referring to his preference for using profanity, allowed that “it’s the fastest way to get the job done” (Conover, 2001, p. 69).



Conover notes that prison changed his natural disposition from one of calm to one of stress. He writes of the physical response he felt as he entered the prison: “Your stomach lets you know, just before the shift starts, what it thinks of this job” (2001, p. 5). I felt a comparable response in my inability to sleep on Sunday nights. I would lie awake, dreading the uninterrupted stress of the next five days. The stress comes from many places: the inevitable exhaustion that the next day will bring, the knowledge that my students (almost all of whom perform below grade level) are not sufficiently progressing, fear of being involved in one of the frequent physical altercations that take place in the halls, fear of unexpected censure from an assistant principal for any one of countless possible “adminis-trivial” infractions, fear of having to cover an unknown class for an absent teacher, fear of not being able to hack it . . . the list goes on. In short, one feels caught between upward and downward forces. The students — who don’t enjoy being there — present academic and management challenges from below. The administrators, responding to strong demands to raise test scores, put intense pressure on teachers to adhere to strict instructional models and curriculum pacing schedules, despite the school’s chaotic state. Although Conover deals with different anxieties, I recognize and sympathize with his situation:

It was an experience of living with fear — fear of inmates, as individuals and as a mob, and fear of our own capacity to fuck up. We were sandwiched between two groups: Make a mistake around the white-shirts [supervisors] and you would get in trouble; make a mistake around the inmates and you might get hurt. (2001, p. 95)

The teachers are not the only ones who suffer from stress. The disorder that prevails within school walls creates a stressful environment for students as well, which is certainly a determining factor in their poor academic performance and their frequent aggression. Lack of order and discipline go hand in hand with student dissatisfaction and misbehavior, a phenomenon similar to what Conover noticed in Sing Sing. Inmates preferred order, rules, and facilities with strict discipline. High staff turnover and new officers “irritated inmates in much the same way that substitute teachers irritate schoolchildren” (2001, p. 99). Conover concludes that, to some extent, prisoner aggression “had its roots in Sing Sing’s frequent changes of officers” (p. 99).

As noted above, coverage, or the practice of using teachers who have a planning period to substitute teach for absent teachers (our school has enormous difficulty hiring substitutes, due to a lack of interested candidates), is one of the most unpleasant experiences of the job. You walk into a classroom of unknown students who immediately sense your disorientation and take it as license to act as they wish. Given the students’ preference for consistency and tendency toward aggravation at the sight of a new face, you can imagine the effects of the high staff absenteeism rate at our school. One teacher called in sick more than thirty (!) days, and there were several “emergency” days, when ten to fifteen teachers (nearly a quarter of the staff) were out. I took each sick day I earned, one per month.


Get Out or Go Under

Unsurprisingly, and not unlike the officers Conover met in Sing Sing, many of my colleagues and I talk of moving on. Forty percent of teachers at our school — about the same average for other city schools — have spent fewer than two years there (NYC Department of Education, 2002). Just as Sing Sing has a reputation for greater indiscipline and disorder than the more tightly run facilities upstate, many NYC public schools, mine included, appear more difficult and unappealing than their suburban counterparts. I have frequently received the same counsel from experienced colleagues: “Do your two years [the length of the Teaching Fellows’ contractual commitment] and then go teach in the suburbs.”

In all likelihood, I will take their advice to leave — not necessarily to “the suburbs,” but to a school that won’t cause me sleepless nights. I want to work in a “normal” school, where students and teachers don’t scream at each other, you don’t find urine in the stairwells, and I don’t need a supervisor’s signature to make photocopies. I especially want a school where education isn’t understood simply in terms of how well one scores on a citywide exam in April. I know such schools exist, because I’ve traveled to them for classes and meetings. They are clean and orderly, student work hangs undamaged in the hallways, kids go up the “up” stairways and down the “down” stairways, and the fire alarm isn’t pulled every hour. Our school is far from the worst in the system, but I know there are a lot better schools out there, and I want to work in one of them.

I already see the negative effects of our school’s atmosphere on my own behavior and perspective. Conover writes of how the prison’s oppressive environment ate away at his previously held compassion and tolerance, such as when he took comfort in the story of officers abusing an inmate who had hurt a colleague. I noticed a similar coarsening of my spirit during my year teaching. I longed for my more disruptive students to be absent and felt my spirits fall when they entered the room. Despite campaigning to get my students to be more respectful, I felt a mixture of envy and delight when children directly insulted administrators that I didn’t respect. I found myself doing things for which I used to criticize my colleagues; for example, one day in a private discussion with a fellow teacher, I dismissed a particularly difficult student with an expletive. Although I caught myself, I felt a shiver of dread. “Oh no, I’m becoming Mr. Z” [a teacher particularly scornful of his students], I joked, but I felt no mirth. I have observed my colleagues, and I have come to the conclusion that remaining at our school results in one of three phenomena: 1) you cope by falling prey to the inhumanity of the “us vs. them” mentality and act accordingly; 2) you insulate yourself by refusing to care and bide your time until you can transfer or retire; or 3) the stress gets to you and your mental health suffers. None of those choices appeals to me, so next year I will update my resume and begin checking the classifieds. I suppose there is a fourth possibility, in which one could work to improve the culture of the school from inside the classroom, but this strikes me as being as daunting a task as a corrections officer changing a prison’s culture from his/her assigned post. My own efforts to this end, such as making it a point to always be civil to my students, never to raise my voice to them, and to smile a lot, seem nice but pathetically feeble in the context of our school’s dysfunction. As I compare the inadequacy of my response to the magnitude of the problem, my preference is to abandon ship.


Crossing the Bridge to Failure?

In his study of why the tiny African country of Lesotho has not developed economically, political scientist James Ferguson (1990) makes an interesting comparison. The scores of aid agencies that make up the development industry in the country — Lesotho has received no small amount of development assistance from wealthy countries — labor incessantly in pursuit of their goal of development. Despite this considerable attention, however, Lesotho remains one of the poorest countries in the world, belying the efforts and money expended. Nevertheless, the development industry continues to pursue development, apparently heedless of its continued lack of success. This diligent but fruitless devotion to a desired objective, Ferguson argues, bears much in common with the way prisons work. Both fail to the extent that their failure eclipses any successes achieved, but this does not dim their ardor.

Citing philosopher Michel Foucault’s (1977) study of prisons, Ferguson (1990) notes that, while prisons are envisioned as “correctional” institutions, they produce the opposite effect. Instead of reforming criminals, their operation is such that they reinforce a criminal’s delinquency. While at first this might appear to be a failure, Foucault argues that it is, in fact, a success. “The prison, apparently ‘failing,’ does not miss its target” (1977, p. 276). The goal of the prison is not reform, he maintains:

For the observation that the prison fails to eliminate crime, one should perhaps substitute the hypothesis that prison has succeeded extremely well in producing delinquency . . . in an apparently marginal, but centrally supervised milieu. . . . So successful has the prison been that, after a century and a half of “failures,” the prison still exists, producing the same results, and there is the greatest reluctance to dispense with it. (p. 277)

When one examines the dismal academic performance of our school, with only 14 percent of students meeting state standards in language arts, and 75 percent below standards in math (NYC Department of Education, 2002), one begins to wonder if the nature of our school is failure to educate its students. How can such a profound failure be tolerated, let alone allowed to continue? Despite the No Child Left Behind legislation and our status as a “corrective action” school for language arts, failure is indeed allowed to flourish. The administration strives to meet required targets by nibbling at the margins, by trying to push students who are approaching standards to cross the line. Those who fall far below standards — no small portion of the student population — are essentially cut loose and allowed to languish. In correctional facilities, rehabilitation occurs so infrequently that it is considered the exception rather than the norm. In our school, it seems that education is a similarly exceptional outcome. Three out of four students graduate unable to do math sufficiently, and four out of five are unable to read or write acceptably.

A 2002 decision by a state appeals court provides a useful perspective on why this failure exists and continues. The court overturned a previous ruling that New York City public schools were underfunded, a ruling that would have obligated the state to increase its financing of city schools. In rejecting that ruling, the appeals court demonstrated a shockingly callous logic. The New York Times summarized the court’s conclusion that

the state was obliged to provide no more than a middle school education, and to prepare students for nothing more than the lowest-level job. . . . Even if students were not properly educated . . . that did not mean that the state had failed its obligation. “The proper standard is that the state must offer all children the opportunity of a sound basic education, not ensure that they actually receive it.” (Pérez-Peña, 2002, p. 1)

 The court’s definition of a “sound basic education” exposes the failure in their logic. Rejecting evidence that New York’s public schools offer a substandard education, the court ruled that “teachers with poor qualifications, overcrowded schools, poor physical conditions, and schools that do not have libraries, did not mean that the essentials were not being provided” (Pérez-Peña, 2002, p. 1). One would like to believe that, in twenty-first century America, such a school would hardly be seen as providing “the essentials.” In all likelihood, such a school would not be where the ruling judges choose to send their children.1

 Last winter, I stopped to take a look at the bulletin board outside the guidance office. Three flyers were posted; two advertised for local public high schools, each with academic records even more wretched than those at our school, and one highlighted a training program run by a local pharmacy chain. This program offered teens certification in retail sales, and promised those who completed training preferential candidacy for entry-level vacancies. As I walked away, I wondered how the bulletin board outside the guidance office of a suburban middle school must look. There would be brochures for preparatory high schools, as well as for summer programs in art, music, science, and sports. Students would be encouraged to become doctors, lawyers, artists, and executives; at our school, a lone flyer exhorts students to work cash registers.

 Does this mean our school is a failure? Following Foucault’s (1977) logic, one could conclude that, rather than failing, it is succeeding. As the appeals court decided by allowing to continue operation of a school where most children do not learn to read, write, or do math, we “educate” them for the world of minimum-wage, unskilled work. We don’t need to concern ourselves with providing a better education for our students; there are plenty of schools that will do that for other children. We have already taught our children — at least those who do manage to find employment, for some will no doubt become the charges of Conover’s erstwhile colleagues — on which side of the till they belong.



  1. This decision has since been reversed, offering the prospect of much needed hope — and cash (Schrag, 2003).



Conover, T. (2001). Newjack: Guarding Sing Sing. New York: Vintage Books.

Ferguson, J. (1990). The anti-politics machine: “Development,” depoliticization and bureaucratic power in Lesotho. New York: Cambridge University Press.

Foucault, M. (1977). Discipline and punish: The birth of the prison. New York: Vintage Books.

Gladwell, M. (2000). The tipping point: How little things can make a big difference. New York: Little, Brown.

New York City Department of Education. (2002). 2001–2002 annual school report, IS 162. Retrieved May 3, 2003 from

Pérez-Peña, R. (2002, June 26). Court reverses finance ruling on city schools. New York Times. Retrieved May 3, 2003 from

Schrag, P. (2003, June 28). Adequacy in education: Why is clear. But how? New York Times, p. A15.