What I Saw: Of Thee I Sing Sing

Welcome to Sing Sing, 2013

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In the pursuit of physical fitness, something interesting to photograph and the opportunity to take my daughter’s dog for a walk, I have once again run afoul of the local constabulary. Only where in the past it’s been US Navy sentries in gummy boats racing across the harbor to keep me from photographing submarines or Homeland Security agents stopping me from photographing scenes that hundreds of tourists photograph every day, this time it was the screws at Sing Sing prison.

We spent the Thanksgiving holiday with new friends and family who live in a historic neighborhood on the edge of Ossining, New York. (If that name rings a bell, it might be because the fictitious Don and Betty Draper of Man Men lived in Ossining.)

You can’t be in this area and not know there’s a big prison in the center of town. And not just a big prison, but a famous one. Sing Sing, if you haven’t heard of it, is a maximum-security prison just north of New York City. It was built (much of it by inmates, presumably under careful supervision) during the early 1800s. Sing Sing's so famous in American correctional lore that, as the historical market at the entrance proclaims, it's the place that inspired terms like “up the river,” “big house” and “last mile.”

Even by the serious standards of prison architecture, Sing Sing’s a pretty bleak place. It’s gray stone and brick buildings ramble from the top of a bluff down to the Hudson River shoreline. The cement wall that surrounds the prison is tall and as intimidating on the outside as it must be on the inside.

No Parking. No Escape. 2013

My crime, such as it was, was that Hope (the dog) and I didn’t realize that as we walked purposely down Hudson Street through a quiet residential neighborhood we’d unwittingly, and without any warning or further ado, stepped onto the prison grounds.

I photographed the historic plaques mounted outside the prison wall and walked a good mile or so around the eastern perimeter of the prison, stopping occasionally to photograph guard towers or interesting textures in the prison wall. It wasn’t until I’d gotten around to the northern side of the prison that a guard stepped out of a watchtower and yelled down to me to stop taking pictures.

Under normal circumstances I might have protested that I was standing on a public street photographing a scene that is visible from dozens of neighboring homes and two or three major local streets. But the guard was standing thirty feet or so above me and had a shotgun in his hand. All I had was a camera and a dog.

And as it turns out, I wasn’t even standing on a public street any more.

A more observant guy would have noticed that there were several signs posted at the entrance to the prison grounds indicating that it’s illegal to make unauthorized photographs on the prison grounds. I, on the other hand, was too focused on some of the famous people—e.g. mobsters “Lucky” Luciano and Louis “Lepke” Buchalter, Julius and Ethel Rosenberg, Ruth Snyder, Willie Sutton and “Son of Sam” killer David Berkowitz—who’ve resided on the other side of the wall.

Let’s just say I put the cap on my camera lens and walked back to the house by another route. Wouldn’t have been any fun to get tossed in the big house.