Out on the Town: Harvard Square chess hustlers

Regardless of what we Jumbos think of Harvard University, there is no denying that the school has become a symbol of decadent intellectualism. People from around the world associate Harvard with cozy, upper-class success, evidenced by the school’s doubling as a tourist attraction. It is no surprise, then, that the area has become a beacon for chess players to meet and play with one another.

After all, chess and aristocracy go together like salt and pepper. All sorts of folks stop by the Harvard Square chess boards for a friendly game or maybe something more high-stakes. This is where the chess hustlers have seized their opportunity. Camped out at the picnic tables in Harvard Square, these seasoned locals will play with you — for a price.

Recently, I decided to challenge one of them to a game or two to see just how skilled they were. I came away from the experience with a newfound desire to improve my understanding of chess, as well as knowledge of a great pastime quite close by. Our wonderful MBTA public transit system makes it pretty easy to get anywhere in Greater Boston, and Harvard Square is no exception. For those who have not made the trip, there are a few ways one can get there. Personally, I prefer walking to Davis Square and taking the Red Line inbound for two stops. One may also use the 96 Bus, which has two stops on Boston Avenue en route to Harvard Square.

This latter route eliminates walking entirely, which has its own benefits. Either way, the chess boards are right in the square, so they are not hard to find upon arrival. When I first got there, I was petrified of playing. Interaction with strangers isn’t my forte, but after mustering up some courage, I approached one of the men sitting at a board. He looked slightly withered but greeted me with a smile as I introduced myself.

I sat down at the board, which was already set up. He also had a timer ready, which we agreed to set to five minutes apiece. Before starting, he explained to me that he prefers to play with money on the line, so we both wagered $5. He let me use white pieces, so I started off with a slight advantage. However, that advantage gradually disappeared over the course of our game.

Not only did my opponent make good moves, he also dealt with time pressure incredibly well. He never took more than 10 seconds on a move, whereas I would get stuck on a position and spend too long looking for a solution. In the end, I lost on time and forfeited my $5, satisfied. Walking away from the game, I felt like I had come close to winning. Part of me wanted to return the next day and challenge him again. How much of my perception of our skill gap came from his hustling prowess? I have no idea, but in any case, I fully recommend taking the trip to Harvard Square to play chess with some grizzled players.