43 pages • 1 hour read
Ted ConoverNewjack: Guarding Sing Sing
Nonfiction | Autobiography / Memoir | Adult | Published in 1999A modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.
Chapters 3-4Chapter Summaries & Analyses
Chapter 3 Summary: “Up the River”
Criminals once traveled upriver to Sing Sing by boat from New York City, and the prison was built upon the rocky slope rising from the Hudson River. Located in present-day Ossining, housing has slowly become unaffordable on a correction officer’s salary. The new recruits, Conover’s classmates, have found shared housing in poor conditions. The cohort will spend the next four weeks on OJT, on-the-job training.
At the time, Sing Sing is being utilized in many ways as a training facility for new recruits. Thirty-four percent of officers have less than a year on the job, and there are upwards of seven-hundred-and-fifty security employees at the prison. Sing Sing is the second oldest prison after Auburn, and the second largest after Clinton.Sing Sing contains almost two-thousand inmates in maximum security and nearly six hundred in Tappan, the prison’s medium-security compound. There are about two-thousand violent felons, with around sixhundred imprisoned for murder or manslaughter. Fifty-six percent of inmates are black, thirty-two percent are Hispanic, and ten percent areCaucasian. There are few vocational programs, as almost all college-level programs had ceased in 1994 and 1995 due to federal lawmakers ending funding. Five inmates have committed suicide in five months, and the inmate-grievance system receives twenty-five grievances a week.
Conover notes that the recruits are adjusting to a “new groove,” transitioning from the strict nature of their former training regimen to the more flexible rules at Sing Sing. During his training at Sing Sing, Conover is told: “Don’t confide in an inmate about your personal life. And don’t be tempted by bribery or other offers. The moment an inmate gets anything on you, he’ll have power over you and is certain, eventually, to sell you out” (63).
The first glimpse of A-block is drab but stunning to Conover, while the rest of the prison is a maze of corridors, gates, and staircases. The layout is difficult to memorize, but maps are not allowed inside because they are considered a security risk. There is a seven-building “honor block” for inmates who have gone several years without being cited. The solitary-housing unit, known as the SHU or The Box, is bleaker. The Death House was converted to a vocational building after the death penalty was abolished in New York. As a final barrier, there is a double fence with chain link barriers, razor ribbon, and infrared sensors separating the prison from the outside. Tappan, unlike the maximum-security section of the prison, has more flexibility for inmates who are often in their final years before parole. In general, Conover finds that prison rules and guidelines are haphazard, not strictly enforced, and often broken.
For the first two hours of his shift, Conover is assigned to B-block, and, specifically, galleries R-and-W. Conover is tasked with helping Officer Fay, who himself finished training just a few weeks before. The inmates are milling around, with an estimated fifty or sixty inmates out of their cells and on their way back from chow. Conover experiences the first challenges to his authority and patience: one inmate threatens Conover, another inmate asks for his TB meds, and another group of inmates walks through a gate that Conover forgets to lock. The situation is totally disorganized and directionless, and Conover is overwhelmed by both the number of tasks and Officer Fay’s incompetence. Towards the end of the shift, Officer Konoval, a training officer, appears and asks Conover how things are going. Konoval stays briefly, scolds a couple of inmates, and leaves. After Konoval departs, an inmate surprises Conover by throwing a fake punch at Conover’s head.
Over the next three weeks, Conover is assigned to different shifts, to his relief. Conover is assigned to the State Shop with Officers DiPaola, Davis, and Colton. When a senior officer has the group omit information on a Fire and Safety report, Conover realizes the arbitrariness of the rules that the recruits had been inculcated with during their academy training. During a strip-frisk, also known as “Nuts and Butts,” Conover is disgusted by an inmate compliance. Ten days later, in B-block, a red-dot emergency occurs: a guard has mistakenly unlocked a keeplock’s cell, and that inmate has slashed another inmate. To Conover, this incident becomes a lesson in vigilantly protecting fellow officers.
A few days afterwards, in the Q-gallery of B-block, Conover learns that “keys were power…” and that “a lost key was a disaster” (80-81). Officer control over the gates is essential to a block’s security. When Officer Orrico hands over the keys to Conover, Conover realizes that he has lost the keys in the midst of a red-dot emergency. Fortunately for Conover, Officer Don Allen approaches with the keys. Conover again is skeptical of whether he can operate in such a stressful environment.
Conover is assigned to work with various officers, including Martinez, St. George, and Smith. Conover is especially impressed by Officer Smith. Conover attributes Smith’s success to managing a gallery half the size of most others, having a regular post, and treating the inmates in a more humane way. Smith is described by Conover as a “Black Mr. Clean” from Harlem, who is well acquainted with his inmates, but also stern. According to Smith, the trick is to be firm without being nasty or egotistical.
On Conversion Day, the recruits become regular officers.
Chapter 4 Summary: “Newjack”
Conover opens the chapter by quoting J. Michael Yates: “No peace officer with any sense, even in dire circumstances, punches where it will leave marks” (95). Gradually, Conover realizes that the strict lessons of the academy are not enforced with the same rigor at Sing Sing.
In this chapter, Conover gives a more in-depth look into the typical goings-on in various sections of the prison. Generally, he describes it as “a world of adrenaline and aggression [...] an experience of living in fear—fear of inmates, as individuals and as a mob, and fear of our own capacity to fuck up” (95). Moreover, Conover observes that “prison was also a microcosm of a totalitarian society, a nearly pure example of the police state” (95). The new recruits exist on the hierarchy between the white-shirts—who are the superior officers—and the inmates.
Section Summary: “A-Block”
Conover is assigned to A-block often in the first few months. The A-block is a massive building and requires around thirty-five officers to run the building during day shift. Conover decides that it would be best for him to begin enforcing rules, and his first attempt is to bring an inmate’s illegal radio antenna in-line with prison regulations. Although inmates are allowed to have music, there is poor reception in their cells; their makeshift attempts to improve the reception on their radios often result in scattered wires. When the prisoner vehemently objects to Conover’s orders, Conover comes to understand that “In prison, unlike in the outside world, power and authority were at stake in nearly every transaction” (98).
The frequent changes of officers at Sing Sing “irritated inmates in much the same way that substitute teachers irritate schoolchildren” (99). One day Conover is assigned to the block of an officer who has taken the day of. The guard, Officer Michaels, considers the inmates to be decent and “homies”; Conover is faced with scolding stragglers in the hallway and a keeplock who takes a shower in contempt of Conover’s authority.
Among the constant power-plays and battles for authority are also the bending of rules. For example, Officer X (Conover doesn’t provide their real name) tells Conover not to release an inmate, Hawkins, for recreation, but Officer X gives no explanation for the penalty. After Hawkins writes a grievance against Conover, Conover records in the logbook that inmate Hawkins was denied recreation, naming Officer X in the log entry. It is later revealed to Conover that Hawkins had slugged another unnamed officer, Officer Y, the day before, and that Officer X wanted to teach the inmate a lesson. The senior officers first pressure Conover to say that he forgot the exact events of the day, and then ask Conover to redact the name of Officer X from the re-written report. Again, Conover discovers that “If you were going to survive in jail, the goody-goody stuff had to go” (103).
Sergeant Wickersham is introduced as a white, handsome officer who chooses to work at a high-stress post in A-block. Conover writes that Wickersham’s objective appears to be to chew out and bully new recruits, including Conover. After another officer refers to Wickersham as a “bug,” the term used to describe mentally ill inmates, Conover uncovers news footage showing that Wickersham had been taken hostage during a riot in B-block within two weeks of starting at Sing Sing, and that Wickersham had also been a POW in Vietnam.
During one of his shifts, Conover is punched by the inmate in cell P-49 after confiscating the inmate’s mirror. However, thinking upon the positive interactions that he has had with other inmates, Conover reflects that “They weren’t all bad, I thought. Just most of them” (126).
Section Summary: “The Box”
Conover describes the special housing unit, known as the Box or the SHU, as a fate comparable to death. In the Box, purportedly, are the inmates who are “The baddest of the bad” (127). Conover is convinced that the SHU is the section with the “highest testosterone level in the prison” (127), given the nature of the inmates and the large stature of the SHU officers. Conover states: “All I knew about Box inmates was that they were very, very bad. I thought of Agent Clarice Starling approaching Hannibal Lecter’s cell…” (128), referencing the film TheSilence of the Lambs. Nevertheless, after Conover participates in a combative assignment of cell-extraction and forced strip-searches, his perception is shifted by a particularly resistant inmate. Conover registers that the inmate “was renouncing his imprisonment, our authority, the entire system that had placed him there. If enough people did that together, the corrections system would come tumbling down” (135).
Section Summary: “Psych Unit”
The officers use the term “bug” to describe a mentally unstable inmate. There is a high incidence of inmates dealing with mental health issues in Sing Sing, and they are confined in the Psychiatric Satellite Unit. In spite of the overwhelming statistics on prisoner mental illness, the officers generally believe that inmates play a “bug game” to work the system and attain better living conditions than those in the general population. Conover is assigned to escort inmates to medical appointments. The medical staff have a cold demeanor towards the inmates; Conover writes that the objective of the medical team seems to be to manage inmates with daily medications, so that the inmates can return to the general population.
On suicide watch, known as “special watch,” Conover is assigned to monitor an inmate named Morales. Morales is Puerto Rican and frequently suicidal and self-harming: he has resorted to swallowing paint and ingesting pieces of floor tile in attempt to take his own life. Morales shows his scars to Conover, telling Conover that it is the pressure of prison that causes him to hurt himself; for every self-injury, considered an infraction, five dollars is deducted from an inmate’s account. Morales has a negative balance of more than one hundred dollars.
Section Summary: “Visit Room”
Conover enjoys the human, positive element of the Visit Room but also is very saddened by the visits. In the Visit Room, Conover works with Officer Eveillard, who was born in Haiti and is genial with Conover. There is a general curiosity among the officers as to why women remain in relationships with inmates who cannot support them. Conover illustrates his best guess with a line from the movie Birdman of Alcatraz, when a murderer is sent to Alcatraz and the woman he marries tells him that “you’re the only life I have” (156).
Conover briefly describes the Wallpost tower overlooking Sing Sing, Utility I, and Transportation, where he encounters a young black inmate named Hans Toussaint, whom Conover credits with a “mission of self-help and a drive to maintain pride and focus” (168).
Conover’s classmates are gradually transferred out of Sing Sing. One officer, Officer Mendez, turns in his badge after having an emotional breakdown.
Chapters 3-4 Analysis
In these chapters, Conover is forced to rapidly adapt to his job at Sing Sing. By the end of his first work shift, Conover quickly discovers firsthand the constant and concentrated level of stress that is inherent to the role of a correction officer. One of Conover’s earliest lessons is that “If you were going to survive in jail, the goody-goody stuff had to go” (103), and so Conover tries to mold himself to the mentality of machismo as a means of navigating his interactions with both inmates and superior officers. The nonstop aggression and posturing wears on Conover, and when Conover asks another officer how they cope with the work, the officer answers: “I just swear at ‘em” [the inmates] [...] It’s the fastest way to get the job done” (69). Another officer tells Conover that “I just try to make myself go numb” (79).
Officer St. George, who Conover meets in Tappan, the medium-security component of Sing Sing, shows some flexibility when arguing with inmates about a food theft, but he is careful to clarify to Conover that “I wouldn’t piss on ‘em if they was on fire” (86). Officer Melman, feels similarly disdainful towards the inmates:
[He] was fond of referring to inmates, out of their presence, as ‘crooks’ and ‘mutts.’ The conversation left me thinking about the many reasons that an officer might come to regard inmates as savages. If a savage dissed you, what did it matter? And if a savage got hurt [...]who cared? (87).
Dehumanization is the order of the day: as stated by Officer Luther, to the newly converted recruits: “You’re the zookeeper now [...] Go run the zoo” (94). This unsympathetic attitude towards inmates even extends to the medical staff in the psychiatric unit, whose role seems to be confined to prescribing inmates with medications so that the inmates can be returned to the general prison population. When an inmate cuts their wrists and the injury appears to be superficial, a sergeant impatiently and flippantly remarks, “Next time, cut the long way. It works a lot better” (148).
Over time, Conover begins to relish in the demonstrations of force shown by his fellow officers towards the inmates. For instance, when Officer Arno is struck with broom handle by an inmate, the prisoner is brought to the Hospital Building and beaten. Conover’s response is that “A month earlier, I would have reacted negatively to a story like that. But now […] I found in the tale a grain of comfort” (93). In another incident, a protesting inmate is “immediately jumped by the frisking officer and several others” for failure to comply with commands; Conover reflect that “When I heard about it, I was proud, because it showed we weren’t wimps” (85).
Conover also describes his participation in an extraction:
I felt suddenly excited to have been included. Despite the ominous tone, and my better instincts, I’d countenanced enough inmate misbehavior and disrespect to feel invigorated by the thought that this is where it all stops. This is where we draw the line. We were going to follow the rules, and we were going to have our way (131).
However, when the feeling of catharsis subsides, Conover wonders “With the outcome never in doubt, what had we won? What did it do to a man when his work consisted of breaking the spirit of other men? And who had invented this lose-lose game, anyway?” (134).
When Conover meets Officer Smith, he commends Smith:
[Smith treated] gallery work as an art, something you could perform creatively. Interpersonal skills were a big part of it [...]Smith melded toughness with an attitude of respect for his inmates. In turn, he was respected back. What he seemed to understand was that at the root of the job was the inevitability of a kind of relationship between us and them—and that the officer played a larger role in determining the nature of that relationship (92).
Conover is motivated to emulate Smith’s performance, rather than strictly treating the situation as “a gray thing and a green thing, and nothing more complicated than that [...] Somewhere between those poles lay the way I wanted to be” (93). Meanwhile, on his days off, Conover inevitably struggles with keeping his temper under control while caring for his children and interacting with his wife. Nonetheless, even while on vacation, Conover dreams of prison, and of being imprisoned; he remains psychologically tied up in the goings-on within Sing Sing.
