David Goewey

Sing Sing Correctional Facility, Ossining, New York,
April 14, 2003

In the chill of an early spring dawn, Sing Sing prison gathers to honor its dead.

I am standing in the narrow parking lot in front of the prison’s Administration Building, where a small crowd has assembled. The color guard, wearing tartan kilts and starched white shirts, tune their bagpipes. Nearby, the honor guard ready their AR-15 assault rifles for a twenty-one gun salute. Several officials, including the prison superintendent, first deputy superintendent, and an Ossining police representative, are already seated around a podium on the building’s concrete steps. Uniformed staff (corrections officers nowadays--not guards) line up rank and file at the parking lot’s south end near the old stockade gate. The memorial service is a tradition. Every spring for the past sixty-two years, Sing Sing pauses to remember the officers killed during the worst break in the prison’s 178-year history, on Easter night 1941.

A few weeks before the memorial service, I had telephoned the first deputy superintendent and politely requested an invitation. I mentioned my brother, who had recently retired as a lieutenant after thirty years working Sing Sing, and added that I was writing a book about the escape. The first dep said he’d get back to me.

What I didn’t elaborate on over the telephone was that I had grown up in a prison guard family--the grandson, son, and brother of Sing Sing officers. I’d been going to Sing Sing since I was four years old, accompanying my father when he’d drive over to pick up his paycheck. His father had been summoned from sleep to help search for the fugitives the night of the break. Even my mother’s side boasted pedigree. Her uncle was assistant principal keeper under Sing Sing’s famed warden Lewis Lawes. Like it or not, this place was in my blood. When I called back a few days later, the first dep said, simply, "Yeah, you can come. Dress warm."

That was good advice. The sun barely clears the massive gray walls, and the breeze off the Hudson is cutting. But that’s April in Ossining--more promise than gift. I look around; little seems to have changed since my childhood. I spot the guard tower where I used to deliver sandwiches to my older brother Ken. Since he couldn’t leave his post even to come downstairs, he’d lower a metal bucket on a rope. Down by the river is the old Death House. My grandfather used to tell horror stories of an executed prisoner he’d lifted from the electric chair, whose knee tendons were so hot they left burn marks on my grandfather’s forearms. The two-story Administration Building is seventy years old and looks exactly as it did when I climbed its steps as a kid, tightly holding my father’s hand.

Warden Lawes constructed the limestone building in 1928, a grand headquarters from which he could manage the most infamous prison in America and also write his bestselling books. On a hill behind the Administration Building you can see the upper floors of the old hospital--another Lawes creation, at the time a state-of-the-art facility. The escape that killed the officers we’ve come to remember began in the hospital, triggering the disgraceful end to Lawes’s twenty-year career at Sing Sing.

That morning, the convicts are not mentioned by name; their ignominy is obvious to everyone present. But for me, the fugitives are there, too, haunting the event, shadows behind the somber reverence. I see them fleeing while the rank and file musters by the old stockade gate, stopping just yards from the rusting trestlework that carries utility lines across the railroad tracks below--Sing Sing is probably the only prison in the world to be cut in half by busy commuter and freight lines. That peculiarity worked to the killers’ advantage, after the murder in the hospital.

Directly across the Hudson, light from the rising sun spreads across the wooded Palisades, igniting the basalt cliffs that drop to the river. The Hudson is a mile wide at this point, four miles at a northwest diagonal past Croton Point toward Haverstraw Bay. Men locked in cellblocks A, B, and 5 have spectacular, frustratingly open views through the bars. If you wanted out (and there isn’t a man imprisoned in Sing Sing who doesn’t), you might imagine coasting unobserved, west across the river. The killers did.

The rifle shots echoing off the walls startle me--three volleys, like a firing squad perfecting aim. Then the flag is lowered to half-staff, and the bugler plays taps. The officials make brief speeches about sacrifice. The ceremony disperses. The families leave for home; the officers go back to work. Sing Sing returns to the business of mass incarceration, just in time for the morning count.

Perhaps murderous outlaws don’t deserve memorials, but their lives cry out for a closer look. The convicts whose actions shadow this April tradition tell a larger story--of Depression-era New York and of a gang of immigrant sons bonded by Hell’s Kitchen loyalties rooted in a firm waterfront faith. First-generation Irish mostly, but also English, Greek, Jewish, and Italian, they planned carefully and worked hard for their alternative version of the American good life. They might have been factory workers raising families, or even policemen. But something else drove them through 1930s New York, when everyone was looking for a way out. Even once behind Sing Sing’s walls, they kept dreaming. Their common ties lasted short lifetimes and made them buckets of money when most people struggled for a dollar. Toward the end of the thirties, before the Second World War erased their names, their exploits were inked in bold black headlines, and their infamy was confirmed in the predawn hours of Easter Monday 1941.

The story begins, then, in the final spring of an endless decade, at the peak of a holdup gang’s white-hot celebrity, with a group of West Side boys who transcended their wildest dreams, only to find themselves backed to the edge of a wide dark river.