by Ted Conover
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.
CHAPTER 3
UP THE RIVER
The safety of the keepers is constantly menaced. In the presence of such dangers, avoided with such skill but with difficulty, it seems to us impossible not to fear some sort of catastrophe in the future.
—Alexis de Tocqueville and Gustave de Beaumont, writing about Sing Sing in On the Penitentiary System in the United States and its Application to France, 1833
Criminals 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.
Instead of laughing, shaking his head, and denying all this, Wilkin, to my surprise, was circumspect. “No officers, to my knowledge, are selling drugs,” he said. “When they have been in the past and we have learned of that, we have arrested them.
“And inmates don’t run this place—officers do. You will see that with your own eyes on Wednesday.
“And as far as following the rules … we are not an upstate prison. We try to follow them to the letter, and we will expect you to. The new administration is committed to tightening security at this prison. But we are a training facility, and not everything is exactly the way we’d like it to be.”
“Training facility” was not an official designation, the superintendent would later explain; it was just the way things had w
orked out. New recruits came here to answer the chronic shortage of officers, and they had to be trained. Five thousand had started out at Sing Sing since 1988, sixteen hundred of them in 1996 alone. The department had an unprecedented need for new officers right now, apparently due to higher-than-usual rates of retirement and attrition.
A training officer named Hill told us that our job would be unusually difficult, because “OJTs irritate inmates.” Inmates appreciate a constant set of keepers, he explained; they don’t like having the rules enforced differently every day. Not that it was necessarily a snap being an old-timer, either; one longtime employee had had his nose broken during a scuffle in the yard just the previous weekend. Sing Sing had between 700 and 750 “security employees” at a given time; 34 percent of these officers had less than a year on the job.
We broke for lunch, and afterward, we were each issued a baton. Down the row from me, someone noticed that his had dried blood on it. Next, we lined up to have our pictures taken. First, we faced the camera while holding up a little piece of paper displaying our name and Social Security number and the date, and then we turned for a profile shot—just as if we were inmates being processed at a jail. These were “hostage photos,” one trainer told me, for our permanent files, to be released to the press if something happened to us—such as being taken hostage. I laughed, thinking the man had a dark sense of humor. But he was unsmiling and, I slowly realized, serious. As unsettling to me as the photos’ purpose was the fact that they weren’t called something else—say, employee contingency portraits, or some other euphemism. Calling them hostage photos was like saying we were “guards” in a “prison.”
In the afternoon, we learned more about the inmates. Sing Sing is the second-oldest (after Auburn) and second-largest (after Clinton) prison in the state, and at this time it had 1,813 inmates in the maximum-security prison and 556 in Tappan, the medium-security portion. Of the total—2,369—1,726 were violent felons; 672 had been convicted of murder or manslaughter. In other words, between a quarter and a third of the inmates had killed somebody. Other violent felons had committed rape (93) or sodomy (38) or a variety of crimes including robbery, assault, kidnapping, burglary, and arson. Eighty percent were from the New York City area. Forty-three percent were ages 25 to 34. African Americans made up 56 percent of the inmate population, Hispanics comprised another 32 percent, and whites around 10 percent.
Sing Sing is unusual for a large max in that it has few vocational or other programs for inmates. Inmates are still required to work for their GEDs, but almost all college-level programs ceased in 1994 and 1995, when state and federal lawmakers ended the funding. “Now there isn’t much to take away,” the programs director admitted candidly during his brief presentation after lunch. “We’re pretty much down to the bare minimum. We have trouble finding things for all the inmates to do—there are only programs for three or four hundred men.” The gap was filled with recreation: unstructured time in the yard or gym. Up to sixteen hundred men might be in recreation at a given time.
The superintendent had less than a year on the job, too. Charles Greiner, who was fit, white-haired, and soft-spoken, stood before the lectern and told us he had come up through the system, starting upstate as a CO. We’d been told he was more security-minded than his predecessor (who, old-time officers complained, was overly concerned with housekeeping and appearances) and interested in tightening up the prison. He told us that he had reinstituted assigned seating in the mess halls, so that inmates couldn’t sit wherever they wanted. He had tried to make sure inmates were more securely escorted from cell to mess hall and back. Other reforms were in the offing but would be instituted very slowly, “so as to only create a tiny ripple back.” Situated, as we were, on the bank of a huge river, the metaphor suggested the prison was a big body of water and we were all in it together. Create too big a wave, and we would swamp ourselves.
The atmosphere inside the prison was apparently stressful at present. Five inmates had committed suicide within the past five months. An inmate-grievance system had been instituted after the Attica riot; Sing Sing inmates typically filed about twenty-five grievances a week against the administration, but recently that number had gone as high as seventy-five. Two months ago, the entire facility had been locked down in Code Green emergency status, meaning that an area (B-block) had gone out of control. Still, said the first deputy superintendent for security, Sing Sing was “no more out of control than anywhere else.” Yes, he conceded, there had been “lots of cutting lately.” But, he added, “That’s true everywhere.”
On Tuesday, our second day, we learned more about emergencies. Many of us, depending on our post, would be furnished with radios equipped with special “emergency pins.” In case of attack by an inmate—or any violent situation we could not control—we were to pull the pin out of the top of our radio by tugging on the lanyard. This sent a signal to the arsenal, where an operator would identify the radio’s location and broadcast a special message to all the other radios. The “red dots,” specially designated officers on standby for an emergency, would then run there to offer aid. Other free officers in the area would join them. The response was immediate, we were told, and usually impressive.
If things got so wild that the local red dots couldn’t handle it, red dots from down the hill at Tappan (or up the hill at Sing Sing, if it was Tappan that had the emergency) would be summoned. If they couldn’t control things either, the Code Green would be called and supervisors were to send all available officers to the trouble spot. A milder state of emergency, Code Blue, called for ceasing all inmate movement and locking down the whole jail. A Code Blue would be called if, for example, the count came up an inmate short and finding him was the top priority. No officers would be allowed to leave the building; wall-tower officers were to step out onto their catwalks with rifles in hand. Everything would be frozen until it was certain that no one had escaped.
Later that day, we were shown a movie produced by the Department, called Games Inmates Play. The film, starring state COs, was a primer on how not to let inmates manipulate you for their own ends and make a fool or a criminal out of you. It dramatized three situations that, we were told, had actually occurred in the past two years. In one, an inmate “porter” (trusty, in more common parlance) sweeping the floor around the officer’s desk became privy to his football pool and collected evidence from his wastebasket; when the CO wouldn’t help the porter set up his own pool, the porter threatened to turn him in to his supervisors; the CO did the right thing and fessed up to his sergeant and lieutenant. A second CO didn’t come clean soon enough, though. After working near one congenial-seeming inmate for a long time, he’d become so comfortable talking to him that he’d confided to the inmate about some problems at home and a shortness of cash. The inmate offered to help him out by paying him a hundred dollars just to bring in a package from his brother. After hemming and hawing for a while (inmates are forbidden to possess cash, which is almost always connected to drug traffic), the officer finally agreed. The final scene of the vignette showed him pulling into his driveway that night and being arrested in front of his disbelieving wife and kids.
Finally, there was the tale of the civilian teacher who allowed an eager inmate to help her grade papers and confided in him when her boyfriend dumped her. He asked if he could take her out when he was paroled in six months. Yes, she indicated, but then he told her he couldn’t wait; they were caught by an officer having sex in a storeroom, and she was fired.
The moral was: Don’t confide in an inmate about your personal life. And don’t be tempted by bribery or other offers. The moment an inmate gets anything on you, he’ll have power over you and is certain, eventually, to sell you out.
After all these warnings, a training officer finished our second day with one more. “By the way,” he said, “we’ve had a problem lately with brown recluse spiders in the facility.” Three COs had been bitten by the venomous spiders, he said; one officer got so sick that he required chemo
therapy. “So just make sure to shake out your jackets if they’ve been hanging up, or look around a desk before you sit down.”
Spiders—on top of everything else.
It had been driving me crazy to be right next to Sing Sing but unable to go inside. On Wednesday that changed.
As our tour group walked the perimeter fence to the main gate, I noticed that we looked slightly different. No longer was everyone so obsessively concerned with his uniform. Sing Sing, it was clear from watching the training officers, did not care much about the polish on your shoes or the crease in your shirt or the length of your hair. Instead of everyone wearing the long-sleeved gray shirts prescribed by the Academy, some had slipped into the short-sleeved version, despite the still-cool spring weather. Other officers now spurned their black oxfords for more casual boots, especially the lightweight Bates and Hi-Tec brands, which were popular among police. And our belts, newly laden with batons, had begun to spring key clips and latex-glove holders, though no one had told us to put them on yet. A new groove had been set, and officers were sliding into it.
We passed through the front gate and several more as we made our way up the hill. Our group felt very white to me compared to the on-duty officers we passed—and particularly compared to the inmates we saw. But the real revelation came in one tight corridor when our group passed an inmate group of nearly equivalent size. As we tried to squeeze into half the hallway, arms and shoulders didn’t just brush, they rubbed. This wasn’t like the small group of subservient workers we’d known at the Academy or the double-file inmates from the roomier halls of Coxsackie. This was something with mass and energy, something … unnerving. I was thinking how easy it would be for someone with a knife to do some damage to us—and get away with it. Ahead of me, one of the Antonelli brothers suddenly turned around and gestured to us, trying to subtly point out one of the inmates—a transsexual, complete with breasts: nothing you wouldn’t see on any given day in Greenwich Village or on the city subways, but decidedly exotic if you were from rural New York. Bella and Chavez seemed more at home with the mix. As we turned the corner, Bella commented, with some satisfaction, “It’s just like the city!”