Review: Holding the Key: My Year as a Guard in Sing Sing, Ted Conover (2000)

As well as spending seven weeks in the training Academy, and the remainder of a year in the service of the New York Department of Correctional Services, Conover read at least 37 books in the writing of this interesting work of literary journalism. Sing Sing, one of the 71 prisons in the state, is located nowadays in a prosperous residential area of Westchester County. But back in 1825 when it was first planned, the site was a remote quarry that would furnish building materials for the growing metropolis.

The complex procedures used in the maximum-security prison by prison guards — the correct term is correctional officer (CO) — and the air of paranoia that motivates them to act in the way they do, are published for our scrutiny, amusement, savour and judgement. At the time of publishing, DOCS was the second-largest employer in the state. When the book came out, DOCS at first barred inmates from reading it. Then they changed their minds and resorted to excising certain passages from copies distributed in prisons: "Mainly Academy stuff ... along with what to do during a red dot emergency and the ways in which officers were made vulnerable by the antiquated configurations of Sing Sing's exercise yards." Although at first DOCS was dismissive ("'Why would I be interested in the view of a newjack?'" a DOCS spokesperson told a newspaper reporter following the release) Sing Sing COs came to the talk and book-signing organised by the publishers in Ossining, the suburb where the prison is situated.

Conover initially became interested in the book idea after talking to some union representatives. When he approached DOCS with the idea of following a new recruit through training and into the prison "DOCS turned me down flat", writes Conover. After writing up the application form in 1994, he waited several months before receiving notice of his successful application.

A 'newjack' is a newly-graduated OC. On the floors of the prison, they are subject to particular attention by the inmates. They are considered fair game in the endless battle of wills between OCs and inmates.

Sing Sing was a world of adrenaline and aggression to us new officers. 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 and you would get in trouble; make a mistake around the inmates and you might get hurt.

Conover gradually decides that some methods of coping with this dichotomy are better than others. One new officer, who he names Smith to protect his identity, gets his attention because of the way in which he goes about his work:

... it seemed to me that Smith succeeded because he viewed the inmates as human beings and was able to maintain a sense of humor in the face of the stress of prison life—traits that are two sides of the same coin.

Conover is glad to leave the prison for the last time after his allotted year expires, to return to his privileged life of a writer, to his customary pursuits, to get away from the fear and anxiety that has infected his dreams and caused his personality to change.

This is a very satisfying read.