Newjack (11 page)

On the TV screen, we watched as another unsuspecting officer opened a cell and was coldcocked by an inmate; he crumpled to the floor. There was also footage of about six white officers subduing a flailing black inmate in an office. Just when it appeared they’d gotten him handcuffed and pushed against a wall, he whirled around and took them on again. In the melee that followed, the camera was briefly pointed at the floor, walls, and ceiling. The next thing we saw, the officers had piled on top of the man.

But most riveting of all were slides of the upper body of a CO who’d been slashed all around the neck and face and back. An inmate had lured him into a kitchen basement for the attack.

The picture that emerged from all these images was of a group of men who could be only reactive, not proactive, and who spent day after day, as one officer said, “waiting for the other guy to take the first swing.”

The room was silent as the prosecutor turned the projector off.

“Everyone’s got to do their time in the bottom of the barrel,” the union rep had said to our class regarding the likelihood of our initial assignment to Sing Sing. A list handed out to us on our last day by the personnel department showed that it was purely a matter of numbers. Clinton, in the Adirondacks, had 219 officers waiting to be transferred in; that translated to four or five years’ wait for officers like us, with no seniority. Ogdensburg, a medium-security prison even farther north, had 279 awaiting transfer. Attica, near Buffalo, had 140—maybe a three-year wait. Of the seventy-one facilities in the state, only two had no waiting list at all: Bedford Hills, a women’s max in Westchester, and Sing Sing.

Sing Sing, Bloom confirmed to us on Thursday, was where we would all report on Monday. For a few lucky ones, this assignment might last only days or weeks. For others, it was an indeterminate sentence of months or years. That afternoon, we were handed “dream sheets,” the requests for transfer. Most of my classmates would hand one in on their first day at Sing Sing, and most started filling them out immediately.

Rick Kingsley, back when he was showing me around the Washington Correctional Facility, had remembered Sing Sing as the worst nine months of his life, his stint in Vietnam included. “Yeah, it’s a rough place,” an instructor who’d recently worked at Sing Sing told our class. “But,” he said, “you’ll learn more in six months at Sing Sing than in two or three years someplace else.” Sergeant Bloom, addressing us in the chapel on the eve of our graduation, asked for a show of hands from everyone in the room who was scared about starting work on Monday. Everyone knew what the “right” answer to this question was, given what we now knew about Sergeant Bloom. But in this case, I thought, the right answer was probably also the true answer. All of us raised our hands.

Howard Johnson’s, the Academy annex, served as the site of graduation. And the night before, there was celebrating to do. Our session voted to begin the evening at a nearby Hooters; later, back at “800-block,” as one instructor had nicknamed the HoJo building with room numbers in the eight hundreds, matters escalated considerably. Some of my classmates had to be carried back to their rooms in various states of drunkenness; I saw Arno, a total straight-arrow up to this point, passed out on the floor of an upstairs
conference room. At one point, urine streamed past the window of our second-floor room, where Gary and I were getting ready to sleep. But it was probably the fact that motel management phoned the police that led to our being called on the carpet in the chapel the next morning before the ceremony. “I hear that some of you decided to be prison guards instead of correction officers last night,” Sergeant Bloom chastened us. A captain we’d never seen before came in and threatened us, swearing he’d track down and fire the worst offenders. (Nothing, to my knowledge, ever happened to them.)

To my surprise, almost all my classmates had family members packed into the motel’s conference room, where, in dress blues, we were presented with diplomas and badges. It had only been seven weeks, but relatives came in from hundreds of miles away. An assistant deputy commissioner spoke a few words, and our class valedictorian (who, I heard later, decided to seek other employment the following week) said that trained by great eagles, we had learned to soar. My classmates from upstate left for one last long weekend home with their spouses and kids before joining me, down in the bottom of the barrel.

C
riminals used to travel to Sing Sing by boat from New York City “up the river” to “the big house,” some thirty miles north. That’s how both phrases entered our language. The prison’s unusual name was borrowed from the Sint Sinck Indians, who once inhabited the site. It may have meant “stone upon stone,” which describes the rocky slope rising from the bank of the Hudson that the prison is built upon.

Once a lonely outpost, Sing Sing now occupies fifty-five acres of prime real estate in suburban Westchester, one of the priciest counties in the United States. The town that grew up around it, once called Sing Sing, is now called Ossining. Up until the 1960s, prison employees could afford to live in and around Ossining, and in many ways they set the tone for life in the area. Now, however, though the town is slightly tattered—Ossining is far from the most desirable address in Westchester—housing prices have pushed out practically all state correction officers. In 1995, the average two-bedroom rental in Ossining cost $1,525 a month, and the average price for a three-bedroom house was $241,000. Away from “the city,” as many recruits think of Westchester County, the same apartment would cost $350 (in Dannemora, New York, near Clinton Correctional Facility) and the three-bedroom house around $64,000 (near Auburn). The department’s “location pay,” meant to help compensate officers assigned to Sing Sing, is considered a joke—about fifteen dollars a week.

In some upstate towns, the prison is the main event, visually
speaking: Clinton’s imposing wall runs along Dannemora’s main street. But even though it is huge, a visitor to Ossining will have to look to find Sing Sing. And once there, all she is likely to see is a portion of its immense wall. This main wall, some twenty-four feet high, is punctuated by twenty-one distinctive wall towers but is otherwise as blank as a cop’s face. The longest stretch, atop the hillside, runs roughly parallel to the riverbank, a few hundred feet below; extensions at either end angle down the hillside. No single spot on land offers a good vantage point of the whole facility; you can’t even see the main entrance from the street.

But I wasn’t thinking in these larger terms as I drove “up the river” at dawn on that Monday in late April, my first day at Sing Sing. I was just thinking of the one Sing Sing story I’d heard at the Academy that had really stuck with me. I’d been told it three times, and though details varied, the gist was the same: A trainee from the class ahead of ours, a guy I’d met, had walked up to an inmate smoking a cigarette during his second week in Sing Sing. “There’s no smoking here,” he said. “Better put it out.” The inmate ignored him. He repeated it until the inmate told him to get lost. Then the new CO reached over and took the cigarette from the inmate’s mouth, whereupon the inmate struck him on the head or broke his shoulder bone with the CO’s own baton or punched him in the mouth—the versions varied. He was badly hurt over a cigarette.

The story had stuck because the lesson was vague. Apparently, it wasn’t a good idea to pull a cigarette out of an inmate’s mouth. I suppose I already knew that. But what were you to do in such a situation? Write the inmate a ticket for disobeying a direct order? Walk away and lose face? In how many ways would my authority be challenged inside the prison? And how would I react when it was?

Given wrong directions at the Academy, I parked at one end of the top wall, as far as I could possibly be from the corner of the prison where I was due to report. It took fifteen minutes to hustle down a crumbling cement staircase lined with a rusty railing to the main gate and then down more steps, over the railroad tracks to the flat terrain by the river. Outside the prison walls, just a few feet from the Hudson River, are three low, white buildings that contrast with the rest of Sing Sing in their newness and cheap construction. Two are small prefab bunk rooms for officers and sergeants. The third is the Quality of Working Life building, or
QWL, a conference room with sliding glass doors and a wooden deck used for training, meetings, and parties.

Here began the four weeks of on-the-job-training (OJT) that would qualify us to become regular officers (though, technically, we would continue on probation for a full year). I was nervous but excited: Sing Sing, storied and mysterious, was exactly where I wanted to be. And I was glad to be living at home again. For most of my classmates, however, Sing Sing was even farther from home than was Albany. Expecting postings in the lower Hudson Valley, my classmates had begun looking before graduation for cheap, small apartments they could share. Davis, DiPaola, and Charlebois had found one in a bad neighborhood in Newburgh, about an hour north of Sing Sing. Arno, Emminger, Falcone, and some others had found a rooming house—“really, it’s more like a halfway house, with recovering addicts and all,” Arno said—around Beacon. Dieter was staying with Di Carlo and his family. Others moved into the few spaces available at Harlem Valley, a former state mental hospital about forty-five minutes from Sing Sing that was now used to house correction officers. A year before at this former asylum, a drunken CO had shot and killed his girlfriend, also a CO, and a female roommate, over unrequited love. But at twenty dollars a week, the price was right.

We were told to set up enough folding chairs and tables to accommodate the 111 people who remained of our class in four or five long rows. There was a lectern at the front of the room; rest rooms and a kitchen were off to the side. Wearing the same dress-blues uniforms we had graduated in the Friday before, we stood at our tables and snapped to attention when the training lieutenant, Wilkin, entered the room.

Wilkin, a laid-back guy, told us all to take a seat, put our brimmed “bus driver” hats on the table in front of us, and just talk to him for a while. Rumors about Sing Sing abounded at the Academy, he knew. “What have you heard?”

It took a while for anyone to raise a hand.

“That officers here sell drugs,” someone finally ventured.

“Uh-huh,” said Wilkin. “What else?”

“That it’s totally crazy and chaotic,” said someone else. “That inmates run the place, and nobody follows the rules.”

“Mm,” said Wilkin. “What else?”

“That some of the officers are real buddy-buddy with the inmates,” said one of the Antonellis, seeming emboldened. “And
that they won’t always cover your back.” It was black officers I’d heard thus disparaged at the Academy, but Antonelli left that out.