43 pages 1 hour read

Ted Conover

Newjack: Guarding Sing Sing

Nonfiction | Autobiography / Memoir | Adult | Published in 1999

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Summary and Study Guide


Newjack is a nonfiction book written by Ted Conover. Conover, a journalist, spends a year as a correction officer in Sing Sing Prison and keeps a detailed record of events in a spiral notebook. The story takes place largely at Sing Sing, a historic prison located in Ossining, New York. Sing Sing is a palimpsest of structures dating back to the 1800s: spread across fifty-five acres, the prison includes massive cell blocks, a solitary-housing unit, and the site of a former execution building: the death house. The construction of the prison complex is disorderly, the architecture is bleak, and the facilities in want of repair.

Setting out with the objective of providing a transparent account of prison from the perspective of a guard, Conover’s experience begins in the correction officer recruit academy, where he is immersed in a world saturated with masculine aggression and abuse. This mentality translates directly to the atmosphere within prison, where charged confrontations and violent retribution are commonplace. This is a far cry from previous reformist attempts to utilize the prison as a space for restoration and transformation, an endeavor led by Thomas Osborne, a former warden of Sing Sing whose tenure was short-lived. Conover himself quickly adapts to the jaded and hardened attitudes of the more experienced prison guards he interacts with.

Conover gives glimpses of his life outside of Sing Sing, revealing the lasting effects of his time as a prison officer. Although Conover enters Sing Sing believing that the temporal nature of his job might shield him from the worst aspects of prison work, he finds that his behavior at work also translates to his relationships with his wife and children.

Newjackpaints an image of a prison system that has foregone not just the possibility of transformation for present inmates, but for future generations. Conover concludes that prison reform is necessary, not only for the well-being of inmates but for the individuals employed in the prison system as well.