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Authors: Ted Conover

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I checked the weapons, counted the ammunition, made the required phone call to the watch commander to say that everything was okay. I flushed the toilet: It was a steel commode/basin combination, just like the ones in the psych unit. A jury-rigged burner and pot also looked inspired by, if not commandeered from, inmate facilities. I glanced into the ambulance log. One seemed to enter the facility every three or four days, on average. A bunch of memos were stuffed into a clipboard. One was headed DISABLING OF HELICOPTERS. First you were to fire into the rear rotor, it directed. Only after that, because of the high risk of explosion, were you to shoot into the engine cowling. Third, after warning shots, you could “fire to disable any inmates who may approach.” But only if the exploding helicopter hadn’t already wiped all of us out, I supposed.

A second memo, from a captain, seemed aimed at shaking up the tower personnel, who were no doubt a bastion of complacency. “It must be realize
[sic]
by all staff that the perimeter is the first and last lines
[sic]
of defense in maintaining the high degree of security necessary for the secure operation of a maximum security Facility,” he wrote. “We all must be cognizant of the close proximity of this Facility to NYC which is home to a major part of our population …” Blah blah blah.

Another memo, four years old, described the Family Reunion Program, probably soon after its inauguration. Entrance to the family-visit trailers was through the sally port at Wallpost 15, where I would work later. Each unit had an outdoor grill and picnic table, and they shared a swing set; inside, I was told, there was a television, a kitchen, and separate sleeping areas for kids and adults. Married inmates on good behavior were eligible to stay there every few months. The Felon Reproduction Program, some officers called it.

On the memo, a wall-tower officer had penned in a telling editorial change in one sentence.
“Purpose:
To provide for a Family Reunion Program which helps preserve, enhance, and strengthen family ties that have been disrupted as a result of incarceration.” The word
incarceration
had been crossed out, and handwritten in its place was the word
individual
. Family disruption wasn’t caused by incarceration, in other words; it was caused by actions of the individual that
resulted
in incarceration. The distinction was important to officers, who wanted no personal responsibility for the harmful effects of the system.

Down on the street outside the wall, the roach coach honked its horn. I stepped out onto the catwalk and hollered to the driver: “Pizza and coffee?” I pointed to the bucket on the rope, and he nodded. I lowered a five-dollar bill to him and, soon after, pulled up my lunch and my change.

As I ate, I read
CPO Family
, the magazine of the Correctional Peace Officers Foundation, a group that offered money and support to the families of slain correction officers. (I joined this organization.) The best article was written by a New York State officer.

“What would the average citizen say if it were proposed that police officers be assigned to a neighborhood which was inhabited by no one but criminals and those officers would be unarmed, patrol on foot and be heavily outnumbered?” asked Donald E. Premo, Jr. “My beat is totally inhabited by convicted felons who, by definition, are people who tend to break laws, rules, and regulations. I am outnumbered by as much as 20, 30, and even 40 to 1 at various times during my workday, and, contrary to popular belief, I work without a sidearm. In short, my neck is on the line every minute of every day.”

Premo had a good point, I thought, but with the blossoming cynicism of a few weeks in Sing Sing’s blocks, I could see he’d understated his case. Twenty, thirty, even forty to one? How about coming to visit me in A-block or B-block? How about 150 to one?

Looking down the hill, I could see a corner of the A-block yard. Guards who worked towers over a yard had a lot of responsibility. The officers on the ground depended on them for support in case of a disturbance, and yards were a frequent site of trouble. Sometimes, as we’d been told at the Academy, an officer could stop a fight just by turning on his PA system and loudly sliding a shotgun shell into its chamber. Some officers were not shy about actually firing. One OJT who’d been at Clinton briefly told me an officer
there had recently shot an inmate’s finger off, presumably while aiming for something more meaty.

My tower was not responsible for the A-block yard, for which I was glad, because even my partial view of it reminded me of the death of George Jackson, the Black Panther and author of
Soledad Brother
, a collection of letters from prison. Jackson and two other “Soledad brothers” had been accused of helping beat to death a white correction officer at the California prison on January 16, 1970. (Three days earlier, a white tower guard at Soledad had shot and killed three black inmates.) Just before the opening of his murder trial, Jackson was shot and killed by a tower guard at San Quentin, where he had been transferred. The authorities said he was shot because he was armed and attempting to escape. “No Black person,” wrote the novelist James Baldwin, “will ever believe that George Jackson died the way they tell us he did.”

The trash can on the outside catwalk was stuffed with contraband daily newspapers, I discovered, which made me feel less bad about having run back to my car after getting my assignment, in order to pick up a paperback novel. I had learned about this new book from an advertisement on the chalkboard by the front gate—
Killer
, by Christopher Newman. The author, in his acknowledgments, thanked First Deputy Superintendent Charles Greiner (now the superintendent of Sing Sing), and as I read on, I saw that Greiner must have given Newman a tour and a lot of background information about facility operations.
Killer
was about a New York City police lieutenant who was being stalked by a notorious Colombian gunman who had just escaped from Sing Sing.

The scenario was this: The Colombian knew that his best chance of escape would be during an outside medical trip. With his A-block buddies, he created a fake altercation on his way to supper. Shielded from the eyes of COs by milling inmates, he stabbed himself deeply, purposefully creating a sucking chest wound. It worked. He was driven out of Sing Sing through the very gate I sat astride, in an official van that was soon hijacked by his confederates. In the van with the Colombian was a Sing Sing nurse, who was forced to continue treating him.

Greiner, to my surprise, had authorized a book signing for
Killer
near the lineup room. Any book that postulated an escape, I would have thought, would have been anathema to the superintendent. The fact that it wasn’t gave me heart. Maybe Greiner wouldn’t be so unhappy when
my
book came out.

UTILITY 1

Occasionally from a wallpost you would see a decrepit Sing Sing van stop somewhere on the road encircling the prison, and out would pile one officer with a chair and five or six inmates with lawn mowers and Weed Eaters. This was Utility 1, a crew of medium-security inmates whose job it was to mow and clean in the area just outside the walls.

One day I had the job of supervising Utility 1, and though it was supposedly a plum, I found it completely nerve-racking: I was terrified that one of these trusted inmates would run off, leaving me to blame for an escape.

This had actually happened recently to Konoval, the training officer, who had taken a different work crew out mowing near a highway in the Bronx. One of the inmates disappeared when Konoval wasn’t looking, only to be recaptured a few hours later at his mother’s apartment in Queens—luckily for Konoval. Those inmates were supposedly even more trustworthy than mine, and Konoval was supposedly a supremely experienced officer. Thinking of him, I actually felt it was
likely
that it would happen to me.

The inmates and I got into a fight over this anxiety of mine. Apparently, when they mowed the relatively short stretch alongside the south wall of the prison, the regular officer didn’t object if those in the lead went ahead and kept on mowing around the corner. But around the corner was out of sight, and I panicked when they disappeared. Two of them told me they would refuse to work if I made them stay back. “What’s wrong, CO, you scared? We ain’t goin’ nowhere—the towers watch us all the way.”

“Stay in sight,” I said. “If you refuse, I’m writing you up. Or maybe you don’t care about your job.” This was false bravado—I doubt I could have gotten them fired—but it seemed enough to inspire some hatred of me, if not fear.

We had to go back to a storage shed to swap malfunctioning equipment for barely working equipment. To show the inmates I wasn’t a bad guy, I agreed to their request not to take the steep, curvy route that hugged the north side of the facility but to drive a route that was almost as fast, through downtown Ossining. The inmates were mad to see women—any women—and this route was more likely to gratify.

Like several old Hudson River downtowns in the region, from
Peekskill to Poughkeepsie, the neighborhood has seen better days. Parts are a ghetto now, with broken-down stoops, prostitutes at night, and guys playing dice against the curb. There was one corner I had always noticed when I passed on previous occasions. It had a large number of fairly well dressed young men hanging around out front, not drinking or gambling, not visibly occupied with anything except paying close attention to passing cars. The inmates waved at them, and they waved back.

“Looks like a crack house,” I commented.

“Of course it’s a crack house,” said the inmate in the passenger seat next to me. “Been there for months.” He seemed to take offense at some condemnation he heard in my tone. “Just guys making a living is all.”

I nodded. (Two hundred feet farther on and around the corner was a ramshackle wooden house directly opposite wallpost 15. This was actually a CO residence inhabited by a changing cast of upstate officers I had worked with; with no knowing reference to the real one,
it
had been nicknamed the Crack House.) It struck me as peculiar that the crack trade was flourishing openly perhaps a hundred yards from one of the most famous maximum-security prisons in the world.

It had a little bit to do with jurisdictions, I supposed. The Ossining police probably had several crack houses to deal with, and its proximity to Sing Sing did not constitute a reason to go after that one in particular. In fact, the presence of a crack house was not so stunning alongside what I had seen during a day on another plum job, construction.

Officers on construction detail—like the one who had witnessed me getting slugged in the head that day in A-block—accompanied outside tradesmen doing building or maintenance work inside the prison. Once I spent an entire day on top of the Hospital Building, keeping an eye on a crew of roofers who were removing an old surface laden with asbestos and then laying a new one. Essentially, my job was to make sure they didn’t do anything to threaten security, such as drop tools to inmates or leave out dangerous equipment.

During lunch break, I got to talk to a few of them. Like the inmates, they were startled to find that I spoke Spanish. One in particular seemed happy to chat. He hadn’t spoken to any white people apart from bosses since he arrived from Ecuador the year before, he told me. The trip had been a difficult one, and it cost
him over seven thousand dollars: He had flown from Quito to Guatemala, then taken a boat to Acapulco. From there he traveled overland to the U.S. border, crossed over to Houston with help from a
coyote
, and then finally flew on a commercial airline to New York City.

“So you’re still illegal?” I asked.

“Sure,” he said, shrugging and looking at the others resting against the wall, thermoses and lunch bags by their sides,
“como todos nosotros.”
Like the rest.

Here was a man who had violated federal law—a fugitive, technically—actually working inside Sing Sing. Resting against its very bricks. And not afraid to tell an officer.

TRANSPORTATION

Over four days in my first months on the job, I got to enter another realm normally guarded jealously by senior officers: transportation detail. For people who are in confinement, inmates go a lot of places. They are accompanied outside of prison to court hearings (many, though imprisoned, have additional charges pending), to family funerals, to the hospital, and to other prisons on transfer. Officers on transportation detail get to leave the facility, and because many trips spill over from one shift to another, they rack up lots of overtime pay.

I was sent from lineup one day to work with a transportation officer named Billings. Every trip required at least two officers. If a large contingent of inmates was being moved, even more officers went along. That day, however, Billings and I had only one inmate to transport, a Mexican who had a deportation hearing at an immigration court inside the Downstate Correctional Facility, about an hour’s drive away.

We wore sidearms, and it was instructive to witness the lengths to which the prison went to keep guns—even officers’ guns—out of the facility. First we walked out the prison’s front gate and collected the pistols from the Arsenal’s outside window. Then we drove a state van around the perimeter to Wallpost 18, where I climbed out, my arms laden with the pistols, belts, and holsters. I walked to the base of the tower. “Rapunzel, Rapunzel,” I called, waiting for the tower officer to appear and lower the bucket. He didn’t smile when finally he peered over the railing; COs could be
so grim. Then, free of weaponry, we passed through the sally port and went back inside the prison. We placed handcuffs and leg irons on our inmate, helped him into the van, and passed back through the sally port to the outside. Only then, after we had collected our weapons from the wall tower, were we, our guns, and our inmate all finally united inside the van.

The forty-something Billings was an extrovert. He quickly told me about the trouble he was having with his wife due to his extramarital affairs (“I don’t think many men my age
haven’t
had affairs,” he said) and about the tensions at home due to the return of his pregnant, unmarried teenage daughter. We talked about the union’s new disability insurance program, about the vocational shop at Eastern Correctional Facility where all the state’s highway signs were made, and about an altercation in the B-block yard the night before, during which officers had been injured.

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