Talking About Life With the Chess Players of Union Square

Located on 14th Street in New York City, Union Square is one of the most diverse and hectic public spaces in a city known for being diverse and hectic. There’s the group of Hare Krishna who congregate to dance and chant over a steady, thumping drum beat; the men selling toy, glow-in-the-dark helicopters that they launch in the air; the street performers of all kinds. There’s the subway station that connects three train lines coming from completely different parts of the city. There’s even a farmers market four days a week, and women peddling cats close by. And then, in the southwest corner, there are the chess players.

New York City is home to many public places populated by chess players, most notably Washington Square Park in Greenwich Village, famously depicted in the movie Searching for Bobby Fischer. In these spaces, people play for money. They set up a board and try to solicit passers-by for a game, for which they charge a few dollars. What’s unique about the Union Square chess scene, though, is its integration into the city’s landscape. Visible by people in cars, on foot, or just getting out of the subway, you don’t have to be strolling through the park to see it.

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A chess player myself, I’ve often stopped for a game or two when passing through Union Square. Over time, I formed a friendship with one of the players named Carl. Since there are so many players there at one time (perhaps 20 when it’s busy), there is some competition for spots. Usually it’s the most vocal or engaging player that gets the most games. But Carl is reserved and polite. His alluring edge on the day I met him was that he was stationed under a bright red umbrella right next to the subway entrance. When he called to me, I was only a few feet from him, and couldn’t resist a quick game. That game turned into four, a long conversation, and the exchanging of phone numbers.

When I interviewed Carl for this article, he’d only been playing at Union Square for a month and a few weeks—a relatively short time among the park players. Like the vast majority of them, Carl has had no formal training. But playing with Carl, it’s clear he’s a natural, developing attacks and lines of play far beyond anything he could have been taught. I asked him if he was one of the better players in Union Square.

“Oh certainly,” he replied. “I’ve made it my business to play them all. Trust me. I’ve been honing my skills, because I figured if I’m going to come into the field to benefit financially, I have to be on top of my P’s and Q’s. I can’t come into an environment charging people or asking for donations and not know what I’m doing.”

Carl came to New York from American Guyana at the age of 12. As a teenager, he was fascinated with transportation, and began driving an ambulette. But one day when he was driving, he hit and killed a child who had run into the street. As a result of the incident, Carl lost his license. After the traumatic event, chess took on a greater importance in his life.

“Right after the accident, this game of chess was like therapy for me. It soothed me, it helped me collect my thoughts and reflect and think about things in a positive and productive manner. So every opportunity I got, I would be playing chess or brushing through certain books in Barnes and Noble.”

I assumed that was when Carl discovered the game, but he quickly corrected me.

“I graduated from Erasmus Hall, in Brooklyn, 911 Flatbush Avenue,” he said. “And anyone who’s anyone in the field of chess knows that Bobby Fischer attended that school. During my senior year of high school, I found out that information and I just fell deeply in love with chess. Once I realized that Mr. Fischer walked the halls of Erasmus and breathed the same air as I did, that was like nitrous in my lungs right there man!”

I asked Carl again a couple times in amazement and he confirmed: Once he found out he went to the same high school as Bobby Fischer (widely regarded as the greatest chess player who ever lived), decades apart, he decided to take up the game himself. It seemed almost novelistic—a character compelled to alter the course of his life after hearing a piece of information that would amount to trivia for most. You could almost imagine him feeling the presence of Fischer’s ghost in the hallways of Erasmus.

Carl’s reality, though, is something different. He told me he was unemployed and having difficulty finding full-time work. Despite his initial dreamy inspiration, playing chess is now a practical decision—a way to try to make ends meet. But as one would imagine, it’s not easy. Carl estimates he makes $50 to $100 during the week—a bit more if he works on the weekends. Talking to the some of the other men at the park, it seemed this was a fairly typical experience.

Each player more or less charges the same per game (five dollars), a kind of de facto price regulation that has developed over time. The games are generally timed, with each player given five minutes on their clock to complete their moves. (If your clock runs out, you forfeit.) This time constraint keeps the games short, allowing for more games to be played per customer, and per day. Indeed, they’re so short it’s hard to play just one. But the quick games are also an advantage to the park player—inexperienced players will not have time to formulate their moves, and players who are schooled in chess are mostly taught to take their time and not rush. Since the park players play under these circumstances every day, the lack of time is not as big a detriment.

In fact, many have tailored their game to fit the time constraint. One strategy is to lock up the board with a strong pawn structure that stifles the opponent’s ability to attack and forces blunders. Another is to produce a line of play that the opponent has likely never seen before and thus takes more time to process.

This was the preferred tactic of Twitty, the second man I spoke to. Twitty, who goes by Twitty from the City, grew up in the Marcy projects in Brooklyn. He is African American, and probably in his forties, though he wouldn’t tell me his exact age. He works security at John F. Kennedy Airport and comes to Union Square on his off days. Playing chess was a way of life in his family growing up; his sister taught him when he was just seven years old:

“Well, see, I was forced to play. I wanted to box, but my mom didn’t want me boxing, so she said, ‘You’re gonna learn to play chess.’ You know why she wanted me to play chess? Living in the projects is dangerous. My younger brother had already got killed. See, when you play chess, you don’t go outside a lot.”

But it was also a means of survival. Twitty and his siblings—”We had eight people in the family so we were better than a chess club,” he said proudly—soon began using chess as a means to earn money.

“We would go out and play for money and bring it back to buy food. When we come in, we always gonna play each other, we were in the house a lot. Then people come to our place and want to play and my mother said, ‘Yeah, it’ll be one dollar to come in to play.’ So we ran it out of the house.”

Twitty’s Union Square operation was probably the savviest I encountered. Unlike Carl, who is quiet and decidedly respectful, Twitty is a one-man show. He dresses loudly, often wearing red and black, matching the color of his board (one of which he hand-painted), and wears two watches at once. His riddle-like quips persist throughout the game.

“You know why I wear two watches?” he asked me. “Because it’s all about time.”

Twitty sits near the sidewalk and can be heard bellowing, “Chess playaaaaas,” a call to the passers-by. Correspondingly, of the players I faced, he played with the most bravado—as highlighted by the time he tried to join his junior high school’s chess club.

“I remember when I was in Montauk Junior High School 223, the whole team was white. So I came in and asked if I could play some chess and they said, ‘Nah this is only for chess players who could really play good,’ and I say, ‘Well I could beat everybody in here, so it’s no problem.’ And they said, ‘Nah, I don’t think so.’ So I said, ‘Well, let’s play some chess.’ Boom! Crush ’em, crush ’em, crush ’em, crush ’em. And we were playing without a clock but I was moving quickly to make them feel like there was a clock. And they didn’t know what to do. So I told them, ‘Just because I’m black and you’re white doesn’t mean I can’t play chess. That’s what you thought, that’s why you rejected me when I walked in the door. I just came here to play chess, I didn’t come here to play your color.’ ”

I couldn’t help but point out what was fairly obvious—chess is a black and white game. Of course, this was apparent to Twitty, too, but in the moment, I couldn’t tell whether he was talking about skin color or the pieces.

To Carl, chess was something that immediately gave him a sort of cosmic purpose, and later brought him solace in a trying time. To Twitty, chess likewise represented something more than a game. Although he didn’t state it directly, it provided a place for him to self-actualize. The discrimination he faced in life was something he could defeat on the chessboard—and not only defeat, but defeat poetically, allowing his opponent to think he had an advantage by playing white (white moves first in chess), and then exploiting that overconfidence.

The third man I spoke to, Alfred, seemed to share this sentiment, only more overtly. Alfred was soft-spoken and looked a bit older than Twitty, although when I asked how old he was, he responded, “Oh, I’m there, I’m there.” He had a sort of lanky grace about him that was only emphasized by the slight drawl in his voice.

I asked Alfred what drew him to chess.

“It always fascinated me, things that could boost your ego, self-esteem. And it’s always good to be good at something in life, anything, whatever it is. If you’re a janitor, be the best janitor. It’s the same thing with chess. What better way to do it than to meet someone who was born with a silver spoon in their mouth. You don’t have to be jealous of him, but you could take your frustration out on him in chess. It’s an equalizer, man, it brings us all to the same level, you know? Which is what you know, not who you know.”

Like Twitty, Alfred viewed chess as a meritocracy. There was metaphor in Alfred’s perspective, to be sure, but it had none of Twitty’s heroic racial subversion, or even Carl’s spectral compulsion. He was all too aware of the justice he wanted to mete out on the chessboard, to the point where it hardly seemed symbolic. I was almost disappointed with how direct he was about it.

But Alfred was also more mysterious than the other men I’d spoken to. So I asked him what he’d done for work before coming to Union Square. His response simultaneously told me nothing and everything about him.

“Oh I’ve done many things,” he began. “I’ve been a puppet, a pauper, a pirate, a pawn and a king,” he started, staccato. Before recognizing that these were the lyrics to “That’s Life,” famously sung by Frank Sinatra, I couldn’t help but imagine that Alfred was creating his own personalized chess set with his different personas as pieces on the board. It wasn’t until that moment that I realized the song even contained a chess allusion (“pawn and a king”); I wasn’t sure if he did either, but that was part of his sly charm.

“I’ve been up, over, down, and out. But I know one thing. Each time I find myself flat on my face,” Alfred continued. As he went on, I understood that his relationship with chess was more than just a way to work out frustrations on the privileged. Playing chess, the game itself, was a way of playing out his life story.

Here he accented every quarter note. “I pick, myself, up, and get, back, in, the race. Because?”

And then he paused.

“That’s life.”

Giancarlo T. Roma is a Brooklyn-based writer, musician, and former competitive chess player. Follow him on Twitter.