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43 pages 1 hour read

Ted Conover

Newjack: Guarding Sing Sing

Nonfiction | Autobiography / Memoir | Adult | Published in 1999

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Essay Topics

1.

Conover writes that “While everyone knows that prison can warp or distort the personalities of prisoners, few stop to consider how it can do the same thing to those who work inside” (107). What examples does Conover provide to explore the effects of vicarious trauma? How does Conover himself illustrate the effects of vicarious trauma?

2.

In Sing Sing, suicide watch is known as “special watch.” When Conover is assigned to “special watch,” an inmate, Morales, who frequently is suicidal and self-harms, tells Conover that it is the pressure of prison that causes him to hurt himself (148). How do prisons perpetuate cycles of abuse and self-harm? What examples does Newjack present?

3.

Newjack captures the male tendency to engage in masculinity when Conover states “most men, [when] meeting other men, instantly asked themselves: Could I beat him in a fight?” (247). How does the book demonstrate the function of masculinity in prison? To what degree does masculinity inform Conover’s ability to assimilate into his position as a correction officer at Sing Sing?

4.

Conover informs the reader of Sing Sing’s racial demography: fifty-six percent African-American, thirty-two percent Hispanic, and ten percent white (61). Later, he calls himself “a son of privilege” (245). How might the author’s position as a middle class white man shape his perspectives and experiences interacting with a predominantly poor and marginalized population? How might his positionality affect his ability to accurately represent the typical experience of correction officers?

5.

Do Conover’s conclusions about inmates and officers mirror or deviate from common racial stereotypes?

6.

During training, the author notes how stringently his instruction to become a correction officer was tailored to the rules of prison policy. He observes that “prison was also a microcosm of a totalitarian society, a nearly pure example of the police state” (96). Later, Conover discovers that following policy is a rookie mistake, writing: “If you were going to survive in jail, the goody-goody stuff had to go” (103). What are the implications of authorities being able to bend the law according to their own needs or circumstances? Compare and contrast the use of law as a strict tool in officer training versus the law as a malleable policy within the context of prison.

7.

To what degree, if any, does Conover’s experience as a correction officer transform his perspectives towards prison as an institution?

8.

How does the author make a case for prison reform? What reforms does Conover propose outside of incarceration? How might community investment serve as a mechanism to disinvest from prisons?

9.

Discuss sexual orientation and homophobia among the inmates and officers at Sing Sing.

10.

Reflecting on his time as a correction officer, Conover writes that “It was as though I’d spent a year as an exchange student in some exotic Third World backwater [...] long enough to learn some of the exotic language, survive some of its brutal customs, and become fond of many of the locals—and now I’d never be back, would never need that hard-won knowledge again” (318). To what extent does Conover’s investigation in Newjack embody a form of journalistic voyeurism?

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