Union Square is probably the place in New York that I visit most. Living in Lower Manhattan and visiting Midtown a lot makes it a central hub. When I walk through it, I always wonder about all the people sitting around offering games of chess (and other games)! What are they doing? Is it a scam? I’ve got answers!

I like chess, I used to play it when I was growing up (it was my sport of choice) and sadly in more recent times I haven’t played all that often.

So when I saw the people offering games in Union Square, I was quickly drawn to it, but my spidey sense was tingling in the back of my head: That doesn’t sound right… There’s no such thing as a free game of chess for no reason; not in this city surely!

What’s the deal with the chess players?

Most of these players use their games as a revenue stream, and for some it’s quite lucrative:

Now he [Ambakisye Osayaba] earns up to $400 a day, taking on all comers from a 2-by-2-foot fold-out table, chairs and chess board he rolls in a metal shopping granny cart every morning to the southwest strip of Union Square Park.

On the whole, they’re friendly people who love playing chess and love to get you to sit down and play against them in a timed or un-timed game. Some are actually happy to help you learn how to play along the way (for a little extra cash).

Is the chess in Union Square fair?

You’ll hear mixed reports when you look into the legitimacy of the games, but I’m not here cast aspersions because on the whole, the games are legitimate and they’re there to beat you straight up in chess.

So how do they do it? Well, to put it quite simply, they’re very good at chess!

One big thing about being good at chess is playing a lot and these guys and girls play a lot. So the hustle isn’t from cheating you out of your hard-earned dollars, it’s beating you without breaking a sweat.

There are stories about how some players will modify positions of pieces on the board if they’re looking down but from people I’ve spoken to, this really isn’t the majority of players’ game.

How do you play chess in Union Square?

Easy! Walk up to someone and ask them the deal. Take for example the guy I mentioned before, Osayaba:

Osayaba charges $3 for a no-wager game. If you want to bet, the winner gets $5. He offers 30-minute lessons for $20. He plays at the park year round, rain or shine.

Technically gambling is illegal, so I think it must stay a little hush-hush if you’re looking to win some money.

Tips for playing chess in Union Square

Well. There’s really only one tip: Be really good at chess or it’s going to be a demolishing.