Newjack: Guarding Sing Sing

Dieter is Conover’s classmate and bunkmate during corrections officer recruit training. He is a former soldier who brings aspects of his military training into his training at the officer recruit academy. Conover develops a dislike for Dieter, who has a mutual dislike for Conover. Dieter threatens to shoot Conover in what at first seems to be a crude but joking manner; over time, Dieter verbalizes more perverse desires to cause harm towards women and animals. Conover is eventually assigned a different roommate, much to his relief.

Officer Smith, who is described by Conover as the “Black Mr. Clean,” is an officer who lives in Harlem and moonlights as a dry cleaner. Smith is in charge of a handpicked gallery, which is half the size of most. Conover believes that Smith succeeds where other officers have not because Smith views inmates as human beings and also maintains a sense of humor. Smith is familiar with his inmates and their offenses, is flexible but stern, and is aggressive when necessary. Nonetheless, other officers disapprove of how Smith runs his section.    

Described by Conover as a white and handsome officer, Sergeant Wickersham is a senior officer at Sing Sing who chooses to work in a high-stress post in A-block. His objective seems to be to chew out and bully new recruits, including Conover. Wickersham is characterized by his dispassionate aura, never raising his voice, and never smiling. One of the officers tells Conover that Wickersham is a “bug,” a term more often used to describe prisoners who suffer from mental illness. Conover later finds out that Wickersham was both a POW during the Vietnam War and a hostage during a prisoner takeover of Sing Sing.

A keeplock in the R-29 cell, Larson is described by Conover as a tall, slope-shouldered black man with long braided hair. Larson has many inmate visitors come speak to him and is considered the “spiritual” father figure by his fellow inmates for his calm, genial personality. Larson grew up in Alabama, where he was first arrested for assault, and then weapons possession. In New York, Larson shoots a correction officer who is dating the same woman as Larson; Larson is subsequently sentenced to eight years to life. Larson asks Conover about his past and tells Conover that he should be a teacher instead of an officer. Conover enjoys talking to Larson, who, as Conover discovers, is an autodidact who teaches himself racial and political theory. Larson gives Conover hope that the “inmate-officer gap had some chance of being bridged” (230).

Osborne (1859-1926) was an advocate for prison reform and a former warden of Sing Sing prison. Osborne’s position was that a just prison system could help create law-abiding citizens. Osborne established the Mutual Welfare League for inmate self-governance in Sing Sing, but his position as warden did not last for more than a year as he became the target of character assassination and sabotage. Conover sees Osborne’s values serving as a potential foundation for modern-day prison reform.

Margot is Ted Conover’s wife. Conover writes that Margot is initially supportive of his project; however, Conover withholds details of his job as an officer and his secrecy begins to take a toll on his mental health and their marriage. Conover finds himself unable to focus on small talk or subjects which, to him, felt trivial compared to his time working in prison. Conover develops a tendency to be hostile to Margot, his children, and his social circle as a result of the constant stress he faces.