Trangressing the Grid: Adventures On (and Off) Manhattan Island

Late last year, we announced our very first essay competition, which invited submissions of original non-fiction writing inspired by the Manhattan street grid “as paradigm, rubric or muse for urban life.” We held the competition in conjunction with a pair of exhibitions at the Museum of the City New York, on view until July 15th, that mark the 200th anniversary of the Commissioners’ Plan, which became the framework for Manhattan’s urban development. The first exhibition (curated by Hillary Ballon) chronicles the history of the grid and the second (curated by Gregory Wessner) speculates on its future. The essays submitted to our competition — 87 incredibly thoughtful entries from all over the world — explore histories both personal and political, posit futures both likely and surreal, and express contemporary realities that both demonstrate and interrogate the grid’s impact on how we understand and experience the city.

Today, we are pleased to announce the winning essay in the competition, which offers a series of personal anecdotes as a catalogue of transgressions, as if Manhattan’s system of orderly streets and avenues dares the city’s inhabitants to challenge its authority even as its locational specificity ensures that certain images and memories endure.

In the next two months, we will publish two more essays, runners-up, from the competition. Below, read the winning essay, “Transgressing the Grid: Adventures On (and Off) Manhattan Island” by Philip Kay. 


Philip Kay’s father and sister in Peter Cooper Village, circa 1963

1.  Askew
I was born in the old Doctors Hospital on East End Avenue across from Gracie Mansion at the extreme edge of the Manhattan street grid and transported downtown in a taxicab to a building that sat defiantly askew to it.  That was during the newspaper strike of 1963 when my mother and father’s world briefly stopped being explained to them in neat little rows of nine-point type arranged in evenly-spaced columns 100 picas wide. Our apartment in Peter Cooper Village — one of those postwar island-in-the-park developments with winding paths and playgrounds that turned their backs on the city and sought to eradicate the street from our middle class lives — looked out at a forty-five degree angle over the corner of First Avenue and 20th Street.

The very first thing I remember in life is watching through our living room window as the M15 bus, like a great dragon, lurched forward, blinked its headlights and all at once every streetlight, storefront and apartment window for as far as the eye could see — even the clock on the Con Ed tower — went dark. The only lights that remained were the ones lined up in the middle of the streets and avenues around our house. At that moment my whole world was radically reordered and motor vehicles and orthogonal geometry suddenly took on an outsized and sinister importance. (That my sister was screaming in the bathtub only heightened this effect.)

I remember, too, riding on a school bus one morning as my big brother, who would have been about 9, raced through the streets beside it, a spectacle even more thrilling and terrifying than the blackout of ‘65. Either he had missed the bus and was trying to intercept it at the next scheduled stop, or this was some kind of a dare, a pre-arranged John Henry, man-against-machine contest, as the screams of my fellow passengers seemed to suggest. Either way, when we got to Stuyvesant Square at the corner of 17th Street and Second Avenue neck-in-neck and started to make the turn, my brother did the most astounding, unthinkable, transgressive thing: he cut through the park. Diagonally. And it looked for a moment as if he just might pull it off. In that instant he became my hero.


Kay’s brother, Peter, by the recently constructed Verrazano-Narrows Bridge, circa 1968

2.  It Takes a Village
We went to school on the other side of town, in Greenwich Village, where the streets went wacky and double-backed onto themselves. They had names instead of numbers and some of them were only a block or two long. Unlike ours, these streets went at each other at odd angles and as many came to an end as went through to the other side. Even streets where things seemed to line up normally concealed gardens full of strange and interesting people who lived by a different set of rules than the civil servants and middle managers back in Peter Cooper. Behind our school, on the Morton Street Pier, a big black ship, the John Brown, would tie up for six months a year. It was, we were told, a floating schoolhouse that spent the other six months sailing around the world. We weren’t clear whether the kids who went there were being punished, having some kind of adventure or some combination of the two.

In the ‘70s my family moved up to 85th Street and my sister and I would ride the M101 all the way down Lexington and Third Avenues to Ninth Street, where we would wait with the bums for the cross-town to deliver us into this world of basement coffee houses and kind people in pink denim shorts. Once a group of some 100 protestors (Stonewall? Vietnam?) sat down in the middle of Seventh Avenue in front of Village Cigars, completely blocking traffic. Things like that were possible in the Village. Unlike Peter Cooper or the Upper East Side, the neighborhood hadn’t set itself up in opposition to the surrounding city, it was just wired differently.

Kay skating against traffic on 6th Ave, 1990. Photo: Aaron Lilly.

3.  Interstices
Eventually we started going to school on the other side of Central Park, closer to our new home. On Saturdays my friends and I would get high and play a game. Together, two of us would take the train down to Midtown’s most crowded precincts to wander the streets and the floors of the big department stores, each of us waiting for our chance to duck into a doorway or subway entrance that only we knew went through to the other side, to slip inside one of those quasi-public spaces that were then proliferating in the interstices between the skyscrapers and disappear down the next side street, leaving the other one confused, humiliated, bereft. It was not altogether satisfying, this business of “ditching” your friends. There were no cell phones then and you had to wait ’til you both got home to call up and tell your opponent what a sucker he was and explain how you had exploited a little known anomaly in the urban system to leave him in the dust. Too often the game was over as soon as it began, but to a teenager it was a way of demonstrating mastery over a complex and forbidding environment.

At 17, I moved into a studio apartment at Fourth Street and First Avenue and literally roller-skated through the 1980s. The second-hand bookshop where I worked was on West 89th Street, and I felt superior to the Wall Street drones who descended the same flights of subway stairs day after day for thirty or forty years, passing through the same unvarying patches of sunlight and shadow without ever looking up. I, on the other hand, could decide my own route to and from the office every day, every minute. I could stop off anywhere I wanted and drag discarded furniture I happened upon off the sidewalk, without it costing me an extra token. My routes would often take me up and down streets that traversed the grid, through parks and public plazas where cars were banned. It was more fluid that way. But however I played it, whether I hurried or took my time, my commute always took me exactly 35 minutes.


Kay and his mother all dressed up for a birthday party on the winding pathways of Peter Cooper Village, circa 1966.

4. Grand Vistas
It was during those years that I learned that nearby, off-kilter Stuyvesant Street was the only one in Manhattan that truly ran East to West, and I began to question the things I had been taught about how the world worked. One afternoon in the spring of 1983, after months of navigating the same canyons and tunnels and scarcely ever seeing the sky, I was heading up Madison Avenue on my way to work when I looked up and there, dangling directly over my head just above the height of the passing trucks where it seemed I could almost latch onto it, was a hook on the end of a long cable attached to a giant crane. Unlike Saul on the road to Damascus, I didn’t actually fall off my roller skates, but I experienced it as a revelation:  This, I thought, must be what it’s like to be a fish, a bottom feeder. I was trapped.

A week or so later, I travelled to Brooklyn, terra incognita, to breathe. I had looked at a map beforehand and figured I had enough time to poke around for a couple of hours before a celebration of the centenary of the great bridge. I had a vague idea of where I was going, but every now and then I would ask someone how to get to the bridge. “You gonna walk?” they would say to me. “You can’t walk there from here. You gotta take the D and change to R.” Clearly these people didn’t get out much. They lacked the Manhattanites’ confidence that the surface world is essentially knowable and navigable. I got lost more than once and still made it there in less than an hour.

Skating back across the Brooklyn Bridge that day and on countless subsequent occasions, I would marvel at how tiny and bizarre the place where I had grown up really was, a little island poised somewhat precariously between two mighty rivers and vast expanses of land and sky.


A coyote in Central Park | Photo courtesy of Bruce Yolton, via

5. Lone Wolves
In 1993, I moved to the corner of Amsterdam Avenue and 106th Street just north of the Frederick Douglass Houses. Crack dealers worked our corner then and the occasional sound of gunfire came from 107th Street, but I was enthralled nonetheless by my new block for the simple reason that it had its own name: Duke Ellington Boulevard. This was the first time in my life that I had lived on a street that had a name as well as a number. And what a name! I used it sparingly and somewhat apologetically among my fellow New Yorkers. (I live in Harlem now, where only white people call Seventh and Eighth Avenues “Adam Clayton Powell” and “Frederick Douglass.”)  For people in foreign countries, however, “Duke Ellington Boulevard” conjured up something else entirely.

One day, parks officials discovered a wild coyote in the middle of Central Park and the newspapers were alive with speculation about how it got there.  Most people assumed it had crossed over the Henry Hudson Bridge from Riverdale late at night and made its way downtown through Riverside Park.  But where had it crossed Amsterdam Avenue?  I wanted to believe it had chosen Duke Ellington Boulevard, a straight shot with ample room to maneuver. I felt a deep affinity with this lone wolf who I was sure had been guided by some primal memory to pursue her ancestral hunting grounds.  As someone who had been skating around Manhattan every day for nearly twenty years and knew where every gentle rise crested, where the obstacles and the potholes lay, I imagined I understood the landscape in subtle ways that eluded most men or beasts and predated even the island’s earliest settlements.

6. Off the Grid
As a teenager, Central Park was a place to chart your own course, skirt a reservoir, cut across a field or through a grove of trees, and at night and on weekends — when our bus passes stopped working — that’s what we did. Lately, even if I didn’t get there as often as I used to, the park had, just by being there, continued to hold out the possibility of an errant existence. But by the late 1990s Mayor Giuliani and the new Central Park Conservancy had put up so many fences to keep people off the grass that one could barely move.  In the bad old days, if you were crossing the park late at night and saw someone coming your way you would leave the path and head across a meadow. You could trust that, from a distance, he assumed you were dangerous, too, and if, by chance, he started heading in your direction you knew it was time to run. Now the two of you were fenced in on both sides, forced to run a gauntlet, face each other down. On the grid at least one can (and does) cross in the middle of the block.  My hero brother once joked that we should set up kiosks at all the entrances to the park where people would leave a deposit and we’d give them a pair of bolt cutters with which to cut through the fences as they walked.  Once they got to the other side, we would collect their bolt cutters and give them back their deposits.

At the dawn of the new millennium, I sat next to a guy at work who told me that he kept a fiberglass scull in the parking garage at the 79th Street Boat Basin and would often row out onto the Hudson after work. When we were kids, most people wouldn’t go near the rivers they stank so bad.  If you touched them or, God forbid, fell in, you had to get a tetanus shot. But now the rivers had been dramatically cleaned up. After 400 years, it was safe to go back in the water.

It didn’t take me long to order a high-tech, collapsible, 13-foot kayak that you could fold up, fit into a big black bag and stick in the closet. It’s difficult to describe what it was like, after living on this island for nearly forty years, the first time I wheeled that bag down to the shoreline, assembled the kayak and shoved off. Usually, when you leave town, you have to deal with train conductors and traffic jams, people talking on cell phones. You have to pass through boroughs and suburbs before you begin to feel like you’ve gotten away. With my kayak, no sooner have I left the grid than I’m already out of town. Nobody can get in my face. Weather and currents permitting, except for the occasional passing barge, I can point myself in whatever direction I choose. I can circumnavigate Manhattan or head out to Coney, Rockaway or Sandy Hook. I can meet friends for lunch in Hoboken or Red Hook or City Island. People on the train see me studying the subway map and they think I’m trying to figure out how to get to Myrtle Avenue. They don’t realize I’m looking at the blue parts.


Kay in his kayak, circa 2004


Philip Kay is finishing a book called ‘Guttersnipes’ & ‘Eliterates’: City College in the Popular Imagination, the story of how the New York public has used the fabled “Harvard of the Poor” to reconfigure itself over seventy years of tabloid scandals involving communist professors, crooked basketball players, ill-prepared students, and other polarizing figures. He is also the translator of the Barcelona based, biannual magazine, D’Ur: Architecture, Urbanism & Cities Now. He can be reached at

The views expressed here are those of the authors only and do not reflect the position of The Architectural League of New York.


Urban Omnibus Writing Competition

In This Series


lauren February 29, 2012

Great Essay!

Kris Scheerlinck March 2, 2012

You made my day, Philip!
Thanks for the great essay!

kate March 2, 2012

As I read, I walked those streets with you, and wished to be doing so for real. Thanks for this.

Alex Gimenez Imirizaldu March 8, 2012


Ricardo Devesa March 27, 2012

Fabulous, Phillip!
Congratulations, from Barcelona, RD.