Newjack

by Ted Conover

  “Get a clean form and meet me in the back room,” he said, as though doing me a favor. I got there first, and an officer sitting across the room counseled me to calm down. It had been a terrible day even before the shower incident, and now this. If they tell me when I get downstairs that I have to do overtime, I thought, I’ll quit.

  Wickersham didn’t take the folding chair I set up next to mine. He sat in another chair, farther away. Speaking in such a low monotone (the faux-calm tone) that I could barely hear him, he asked what I had done before becoming a CO. “A million things,” I said.

  “Answer specifically!” he thundered, glaring.

  “Taxi driver, construction,” I began.

  “Any military?”

  “No.”

  “You keep showing that attitude toward superiors and you’re going to have a lot of trouble around here, a lot of trouble,” he warned. “Just answer the question, just the facts.” Now he was the prosecutor.

  He told me not to write a single thing on the new form, the implication being that I’d get it wrong. Then he read my report, and red-penned it. My “his cell” became “the cell.” “Who do you think it belongs to?” Wickersham demanded. “The inmate? Or the taxpayers who put out a hundred thousand dollars for each of these cells?” He asked me to tell him the whole story, and I actually had to think hard to remember it, because I had been so overwhelmed on the gallery. Upon hearing that I hadn’t called a sergeant and hadn’t locked the guy in the shower when I saw him there—I’d never even thought of it—Wickersham seethed. “This is an embarrassment!” he pronounced, waving my report in the air. “He’s laughing at you now, saying he fucked you! You thought you could avoid confronting him and then come running to Daddy!”

  “Sarge, I’m not afraid of inmates. I burned rec for two of them today, and—” I began. I knew at some level that I had mishandled the situation, but Wickersham’s approach made admitting a mistake the last thing I could possibly do.

  “An embarrassment! Humiliation!” he repeated several times. As he stood and turned, the CO at the table who had earlier told me to take it easy signaled me to relax.

  “Can I ask a question?” I interrupted.

  “What?”

  “Even if I messed up—and now I see that I did—does that change the fact that he did what he did?”

  The sergeant didn’t answer, just continued mumbling about my crimes and misdemeanors. “An embarrassment!”

  Wickersham stood and, with great theatricality, threw all my paperwork into the trash. I tried to catch his eye as he glared at me, but he looked away. So much for earning his respect by standing up to him. Now my day had been an utter failure. Wickersham began walking around the room.

  “Are we finished?” I asked.

  “I’m finished,” he said. And left.

  A crusty old instructor at the Academy with a flat-top crew cut and a mug of coffee seemingly grafted to his hand told us to learn from his mistakes: He had moonlighted as a local policeman in his off-hours from a prison upstate, and it had broken up his marriage.

  “Enough cop is enough,” he said. “If you’ve got to work a second job, do anything besides police work. And my best advice is not to work a second job at all. Exercise, pursue a hobby, work on your car—anything to get the prison out of your system. Don’t take it home to the wife and kids.”

  I was new enough to the job, that evening in June after the encounter with Wickersham, to still believe it was possible to leave prison behind me at night. After I got home, I went for a run, had a beer with dinner, then helped my two-and-a-half-year-old son get into his pajamas. I was doing well at keeping work off my mind until I noticed his younger sister with her hands on the slats of her crib, looking out. Unnervingly, it reminded me of the same view I had all day long. Like an inmate, she was dependent upon me for everything. These two jobs were too much the same, I thought with disgust. My son, tired but rambunctious, didn’t want to brush his teeth and, struggling, mistakenly hit me in the eye. I grabbed him angrily and shouted, made him cry. Well, there was one difference between him and the inmates, I thought darkly as I tried to calm us both down. He was destroyed when I got mad; they, on the other hand, seemed energized.

  I thought I owed my wife, Margot, an explanation for my temper, but I didn’t know how to begin. Certainly, I didn’t want to fill her mind with all the unpleasant images from my day. She seemed stressed enough by her own job and the many other things she had to do, and so, avoiding the matter, we both just fell asleep.

  I woke up suddenly in the middle of the night, having had a vivid dream. I’d been keeplocked. I’d startled a prison clerk in some grocery store-like setting, and that was the automatic punishment. Whether I was an officer or inmate was unclear, but it suddenly dawned on me, as I sat in my cell, that I’d missed the twenty-four-hour deadline for appealing the charges against me. As a result, I now faced a year of disciplinary confinement. The feeling of terror that seized me was so strong that it woke me up.

  A month or two later, Margot and I took a brief vacation by ourselves in Jamaica. My officer friend Miller had, half facetiously, cautioned me against vacation, saying that in his experience, taking time off almost wasn’t worth the nausea of reentry. But as I packed my swimsuit, sunglasses, and Walkman, I knew it was the right decision. There was another life out there, a good life.

  During my first three days in the tropics, slathered with sunscreen, gazing out over the ocean with a rum drink in my hand, I felt I’d successfully left Sing Sing behind. Then, on my fourth night, I dreamed vividly of Sergeant Wickersham. We were hunting together in the mountains somewhere, on horseback. He was still my superior, but in the dream he was tolerant toward me. Suddenly, he gestured at me to look to the left: Across a ridge, bathed in yellow light, was a tiger. Not an ordinary tiger, but one double the usual size. It looked tame, but I knew it might be very, very dangerous. Shhh, the sergeant said, don’t tell anyone there’s a tiger up here or all the hunters will come and shoot it. Everyone else thought there were no tigers left. He was letting me in on a CO’s secret.

  The tiger had smelled or seen us, and I watched as it sniffed out our trail, came closer and closer behind us. I had the feeling that he was not following us but following me. Wickersham and I, on our horses, rode through a swinging glass door into a room, and soon it was just the tiger and us in there. A trick for you to try, Wickersham said: The tiger’s here because we’re carrying shrimp in our saddlebags. Chew some up and spray it out of your mouth at him. I did so, and the tiger hesitated, then fled—something to do with the seasoning, it seemed. Then the tiger came back and approached me on my horse. I repeated the trick, but this time only by going through the motions. I made him flee by just pretending I was going to spit! This was such a shock that again I woke up, trembling with happiness. Or was it fear?

  I puzzled over that dream several times, and weeks later even wrote to a friend about it. “Seems to me it’s about domination, fear, predation,” Jay wrote back. “You’re caught between two tigers, Wickersham and the mass of inmates; you use an inmate technique—spraying—to defend yourself. The fact that it works is significant: It shows that for all his meanness, maybe you know you’re learning something valuable from Wickersham. But at the same time, he’s a dominating tiger to you.” The tiger coming indoors, Jay suggested, represented prison, a bottled-up wilderness within walls.

  That sounded right to me, but while I was in Jamaica, it was much less clear. All I knew then was that even though my body was two thousand miles away, my mind was still trapped in Sing Sing.

  Many officers were aggrieved by Wickersham, and I was delighted when one of my favorites, Goldman, from B-block, joined the club. Goldman was from Queens, a streetwise, muscled Air Force veteran in his forties, and I considered him a stalwart. One day I’d been pulling the brake on R-and-W when a high-spirited inmate running down the gallery (a rules violation) crashed into my back, almost knocking me over. It was apparently a mistake, though i
n the seconds after it occurred I wasn’t quite sure. During those seconds, Goldman appeared from the stairwell. As the inmate apologized to me, Goldman sized it all up and awaited my verdict: He was poised to jump the guy if I deemed it an attack. I hardly knew him, but I immediately loved him for that.

  Goldman had been on the B-block door one day when a red-dot alarm was pulled inside. Per procedure, he exited the block and locked the gate from the outside. In a few minutes, Wickersham arrived with some red-dot officers from A-block.

  “What did you see?” the sergeant demanded as Goldman unlocked the door.

  Goldman told Wickersham where he thought the alarm had come from, which officers had been involved, and who had responded.

  “You didn’t see anything,” replied the sergeant, dismissing him with a wave of his hand.

  “Hey!” Goldman shouted as the sergeant moved past. “I’m an adult—you can treat me like an adult.”

  Wickersham had turned and, according to Goldman, said, “It’s not my job to baby you.”

  Offended, Goldman filed a grievance against the sergeant. He’d been treated disrespectfully too many times by him, he complained to some B-block officers a day or two later, and was too old to put up with it.

  “Ah, ease up a little,” Chilmark, the officer in charge, counseled. “Nobody takes Wick seriously. He’s a fuckin’ bug.”

  Bug was prison slang for nutcase. I’d never heard the expression applied to a member of the staff before, only to inmates. But it made sense, in light of the other information that circulated about the sergeant. What was known for certain was there for all to see: several circular round scars on his right forearm. He had been a POW in Vietnam, people said. Upon returning, he had started work as a Sing Sing CO and had been there just two and a half weeks when he and sixteen others were taken hostage and held by inmates for more than fifty hours during the B-block occupation of 1983. Those scars, everyone said, were cigarette burns inflicted by his captors during one of those experiences.

  Hearing this story, I checked out some newspaper reports from the time. There was a bearded young Wickersham in a large photo after the incident was over, acting as spokesman for the just-released hostages. Instead of the dominating father figure abusing us for our own good, he was a chain-smoking newjack begging reporters to “bear with me—I’m a little nervous.” Being held hostage—suddenly finding yourself prisoner on a volatile inmaterun Death Row—could damage a person in fundamental ways. I thought about odd Sergeant Bloom. What was the legacy of those terror-filled days to Wickersham’s psyche?

  Perhaps it was the particular context of the B-block riot that had marked Wickersham. In a report to the governor following the incident, a state watchdog gave credence to inmate and officer statements that the sergeant assigned to B-block the night the incident began had arrived at work drunk and had so angered inmates with his inappropriate and abusive orders that they gradually refused to comply with anything the officers said and finally rioted. The backdrop was a prisonwide feeling of rebelliousness: inmates in A-block had been demonstrating during the preceding weeks over prison mismanagement. But it seemed that the one sergeant had set it off.

  At some level, I thought, Wickersham hated our innocence and wanted to cure it through abuse. But on another, by keeping new officers on their toes and keeping the blocks running according to the rules—by being a force for consistency—Wickersham may have been insuring himself against repeating the experience. The work inside was never finished. New officers always needed guidance, inmates always had to be listened to but at the same time kept in their place. Wickersham, I thought, probably derived a sense of purpose from obsessively riding herd on us. Part of it may even have been a generous impulse. But it came wrapped up in all sorts of nastiness.

  In July, I was penciled in for two weeks as officer in charge of the A-block gym. This huge room was filled morning, afternoon, and evening with inmates, and my day shift spanned two of those times. It was regarded as a fairly good post in that you generally didn’t have to spend a lot of time telling people what to do. The regular officer, presently on vacation, had had it for years. Its main downside was risk. On a cold or rainy day, the gym could fill with upward of four hundred inmates, and there were moments when I would be the only officer there with them.

  Depending on the time of day, eight to twelve porters were assigned to the gym. I had to put through their payroll, I was told, and therefore to keep porter attendance. (The twelve to fifteen cents an hour they earned was credited to their commissary accounts.) Because I knew the B-block porters to be a tight and surly bunch, I thought I’d better let the crew know right away who was in charge.

  They arrived before rec was called, supposedly to get a jump on the cleaning. There was a lot to do, because an inspection of the block was scheduled for the next day. The gym had a full-size basketball court with a spectator area around it, a weights area the size of a half court, a table-and-benches zone for cards, chess, dominoes, and similar games, and two television areas. There was also a locked equipment room in front of which sat my desk, on an elevated platform, with a microphone on top. Instead of hopping to work, the porters turned on the TVs and sat down. I turned off the one most of them were watching.

  “Gentlemen, I’m going to be here for the next two weeks and I want to talk with you about when the cleaning gets done and who does what.”

  They sat silently.

  “For example, who normally cleans today?”

  At first, nobody said anything. There were stares of indifference and defiance. A pudgy inmate whose nickname, I would later learn, was Rerun finally spoke. “Don’t nobody normally clean today,” he said. “Tuesday’s the day off.”

  “The day off. So when do you clean?”

  “Mondays, Wednesdays, and Fridays. We know what to do.”

  I tried wresting more details out of them, but they wouldn’t say more. Firing porters, I knew, was a bureaucratic procedure that took weeks; I’d be working elsewhere in the prison before the wheels had even begun to turn. And evidently the regular officer was satisfied with these men. Wishing I’d never started down this path, I finally had to settle for a plea dressed up as an order. “Those ledges up there? They’re covered with dust, and the inspectors will be looking. So tomorrow, make sure somebody takes care of that along with all the rest.”

  “They don’t never check those ledges,” came the quick reply as I walked to my desk. And the TVs went back on.

  The next day, somewhat to my surprise, six or seven of the porters set to work in earnest upon their arrival. For half an hour, they swept and mopped and picked up trash. As promised, they skipped the ledges. The place looked pretty good, and the inspectors never came.

  I began to relax, and as I did, I began to understand the complex culture of the gym. There was, naturally, a big basketball scene—a league, in fact, with prison-paid inmate referees and a scoreboard and games that took place about every other day. The games were often exciting to watch—sometimes even a few officers would attend—but also nervous-making, as the crowds that gathered for matches between popular teams were partisan and players would sometimes get into fights.

  Weight lifting was also popular, and when I was new at Sing Sing, it was intimidating to be faced with the huge, muscle-bound inmates who took it seriously. But soon I noticed that these purposeful, self-disciplined inmates were almost never the ones who gave us problems, and I came to agree with the opinion, generally held among officers, that the weights and machines were valuable. The only complaint I ever heard from officers was that inmates’ weight equipment was much better than what was provided to officers in the small weight room in the Administration Building.

  Beyond these activities, the gym held many surprises. On a busy day, it seemed almost like a bazaar. A dozen fans of Days of Our Lives gathered religiously every day for the latest installment of their favorite soap. Behind them, regular games of Scrabble, chess, checkers, and bridge were conducted with great seriou
sness. (One of the bridge players, known as Drywall—a white-bearded man with dreadlocks—came from 5-Building; more than once when he was late, his partners asked me to call the officers over there and make sure he’d left so they could start their game.) At the table next to the games, an older man sold hand-painted greeting cards for all occasions to raise money for the Jaycees, one of Sing Sing’s “approved inmate organizations.” In a far corner behind the weight area, at the bottom of a small flight of stairs, a regular group of inmates practiced some kind of martial art. Martial arts were forbidden by the rules, but these guys were so pointedly low-key, and the rule seemed to me so ill conceived, that I didn’t break it up. In the men’s bathroom, inmates smoked—also against the rules but, from what I could tell, tacitly accepted.

  A floor-to-ceiling net separated these areas from the basketball court. At court’s edge, a transvestite known as Miss Jackson would braid men’s hair as they watched the game or press their clothing with one of the electric irons inmates were allowed to use in the gym. She received packs of Newport cigarettes—the commissary’s most popular brand—as payment. Miss Jackson seemed a sweet man who was at pains to be noticed: She stretched the collar of her sweatshirt so that it exposed one shoulder, and cut scallop-shaped holes in the body so that it held some aesthetic interest. She often wore Walkman headphones, disconnected, just for the look. She must have been rich in cigarettes, and I wondered how she spent them.

  Out on the court one day, just a few yards from Miss Jackson’s enterprise, four short-haired, long-sleeved, bow-tied members of the Nation of Islam stood in a close circle, sternly chastising another member of the group, who must have somehow strayed. One of them was also a gym porter, among those most courteous to me. The juxtaposition of such opposites—the ideologues of the Nation and the would-be sexpot—reminded me of street life in New York City.