A young man goes undercover and works as a prison guard in training at the legendary Sing Sing prison.

Written by Daniel Bergner and Originally Published in The New York Times on May 14, 2000

In 1913, Thomas Mott Osborne, soon to become warden of Sing Sing prison in Ossining, N.Y., had himself locked up for a week in another state facility in order to publicize the brutality -- to both the inmates and their keepers -- of an American penal system in terrible need of reform. Almost a century later, beginning in 1997, Ted Conover, a journalist with a reformer's dreams, undertook a similar but much more long-lasting transformation: he worked, for a full year, as a Sing Sing officer, a rookie, a ''newjack,'' trying desperately to keep order and keep himself intact within the penitentiary's antiquated cellblocks, its decaying catacombs, its embattled Special Housing Unit, ''a place of punishment within a place of punishment.''

Osborne, as Conover tells it within his own story, acknowledged the obvious limitations of his metamorphosis. As chairman of the New York State Commission on Prison Reform during a fleeting period of relatively high social conscience over prison conditions, Osborne made no attempt to conceal, from convicts or guards, his identity or his purpose while briefly incarcerated. Yet Osborne maintained, Conover writes in oblique support of his own method, that ''our inability to ever put ourselves precisely in the place of another should not keep us from 'constantly studying and analyzing the human problem.' ''

Oblique support is plenty, because Conover comes as close as possible to actual transmutation. He told no one he was a journalist. His was no Plimptonesque adventure; Conover was nothing like the self-declared reporter taking a delusional turn calling signals in the Detroit Lions huddle or throwing pitches from the Yankee Stadium mound. He was there for real, in what may well rank as the most anarchic penitentiary in the state, the place his training academy classmates hoped to transfer away from as quickly as they could. To write ''Newjack: Guarding Sing Sing,'' Conover became his subject.

He became part of a system staggeringly vast (1.8 million Americans are currently incarcerated) and bereft of rehabilitative programs or even, at places like Sing Sing, the faint pretense of elevating ideals. Sing Sing, as Conover relates, can't even provide enough busywork to keep the inmates occupied and less prone to violence. And the personal changes Conover tells of undergoing there run far deeper than surface, deeper than the uniform or the ring of keys he describes in reverent detail (''the pewter-colored cell key was the biggest, its shaft as thick as a Mont Blanc pen''), deeper than the dangerous or deadening routines, the herding of throngs of volatile men into their cages (or through a breakfast line where much-coveted waffles are being served), the staring for an entire shift into a single cell, awaiting an inmate's next bowel movement in case he should pass any contraband. The changes reach the level of psyche.

Conover begins his narrative cherishing a secret wealth of sanctimony. During his time at the training academy, he is forced to room with an ex-marine named Dieter: ''I can't remember having met a person who was more unlike me than Dieter. Our every habit was opposite -- he rising at the earliest moment, I catching a few winks; he enamored of the martial life, I skeptical or oblivious of it; he in love with firearms and hunting, I indifferent; he a smoker and drinker, I doing little of either; he fond of gay jokes and full of violent fantasies about liberals and women, I counting among my friends many who are gay, liberal or female or all three.'' Conover's righteousness can seem remarkably unsophisticated, but soon enough his morals are tested by his own natural aggressions, and he gives us the horrifying thrill of watching him revel in the roughing up of inmates, an unsettling pleasure made all the more gratifying for the reader because the author is, in effect, battering his own pieties.

By the time Conover, midway through his year, heads for the Special Housing Unit to take part in that roughing up, his straightforward sentences have accomplished something formidable: he has made us fully part of his experience; he has made us share the vengeful feelings he harbors toward the men he is supposed to control. We have seen him spat on and punched in the head; we have witnessed his female partner being courted as she patrols the tier: ''Hey, Red! . . . You ain't gettin' enough, are you, Red? . . . I'm gonna give it you!''; we have heard about the masturbators who try to ejaculate on the female correction officers and about the countless officers who've been attacked far more brutally than Conover has. We have learned, too, about an inmate ''nicknamed Mr. Slurpee, who would project a spray of urine and feces at officers -- from his mouth.''

So we have begun to appreciate the pep talk given by one of Conover's supervisors: ''You're the zookeeper now. . . . Go run the zoo''; and we feel that the relationship between officers and inmates is, in all but the strictest sense, war -- whereby we are led to ethical surrender. Hey, the giddy logic goes, all's fair. The Special Housing Unit, more commonly called ''the Box,'' is where Sing Sing convicts are put into solitary confinement after severe infractions. It has ''the highest testosterone level in the prison, and somehow smelled like it -- close, musty, with an acrid whiff of perspiration.'' Sent there as part of a strip-search team equipped with helmets and flak jackets, Conover writes: ''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.'' He marches in as part of a vanquishing army, and we, too, feel invigorated. And in this compelling and inescapable way, Conover proves his point, that everyone is dehumanized within the world of our prisons, that even ''normal men'' among the officers become ''violent once enmeshed in the system'' and that such a world is better at creating animals than at civilizing criminals.

Yet in making his case through his own immersion, the author pays more than a psychic price; he pays a literary one. Deep as he takes us into Sing Sing itself -- and it is hard to imagine any journalist doing this more daringly or effectively -- he fails to take us inside the characters who populate it, who work or live there for as long as their entire adult lives. Almost breathlessly we turn pages as Conover's own transformation takes place, but once this story culminates in the Box scarcely halfway through the book, it's as though the reporter found himself trapped within a role that forbade him to do what a reporter generally does: ask questions.

What are the stories of the men he is guarding and the officers he is guarding them with? We meet the abusive Sergeant Wickersham, who, Conover learns secondhand, was once held hostage during a cellblock uprising; the obese, trouble-shooting officer called Mama Cradle; the psychiatric ward inmate the author plays chess with; but the attention given them is so glancing, providing so little of the past or the internal present, that quickly these personalities join the indistinguishable gallery of figures Conover has named and left unexplored. We read, too, of the Haitian C.O. who has just returned from a vacation in the Dominican Republic: he has fallen in love with a Spanish-speaking woman and now has a Hispanic inmate writing his love letters. But this unforgettable triangle is gone from the page within a few phrases.

In his earlier, much-acclaimed book about illegal aliens, ''Coyotes,'' Conover mixed intervals of going under cover with periods of simple in-depth reporting. At Sing Sing, dependent on the protection of his colleagues and rightfully afraid for his safety if his true profession were discovered, he seems to have made himself so inconspicuous and unintrusive as to negate part of his power as a journalist. To a crucial degree, his predicament was forced upon him. When he applied, as a traditional reporter, to prison officials for permission to follow a new recruit through training and onto the job, the officials did what most do in this country when it comes to all aspects of our penal system -- they denied media access. Still, one wonders whether, having sneaked his way in, Conover couldn't have pursued a few more extensive conversations; one regrets that in becoming the heart of his subject he leaves a great deal of the heart closed off.

A fair stretch of the book's second half is powerfully brought to life, however, by Conover's skillful account of Sing Sing's past. Here is his true supporting cast: Warden Osborne, with his dreams of inmate self-government; Osborne's predecessor Elam Lynds, who exercised such torturous control that he compelled his unmanacled, uncontained inmates to build their own penitentiary walls; the hatchet murderer William Kemmler, still gurglingly alive two minutes after Sing Sing's first electrocution was brought to a temporary halt; the electrician John Hulbert, who presided over the death chamber until he committed suicide in his cellar; and George Westinghouse and Thomas Edison, who saw their financial prospects grotesquely tied to which type of current, AC or DC, would be used for executions. Together these characters reveal a story of absurd and unconscionable comedy, the narrative that is the history of corrections in this country. It's a history as memorably encapsulated here as in any writing I know of. So, while Conover's year as an officer may fade a bit in vitality as his book comes to an end, ''Newjack'' coheres as a moving indictment of our ways of punishment. Even more troubling, the book reminds one that almost a century ago, in Thomas Mott Osborne's day, people believed, as we no longer seem to, that society could fix a penal system so plainly a human disaster.

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