Newjack by Ted Conover

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
    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, visuallyspeaking: 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