New York’s Chess Hustlers

In the streets of New York, there is a public underground of gamblers and “hustlers” that earn their meager income through cutthroat games of chess. These so-called “chess hustlers” ride a fine line of practicing illegal gambling in public areas like Central Park and providing vast amounts of knowledge to fellow chess players from around the world, all at a price.

The term “hustler” carries a negative connotation as it generally denotes an individual as one who gains money through “fraud” or “deceit”. In the world of chess hustlers, it is certainly common to come across players who will practice illegal moves and pester their opponent with banter or “trash talk” in order to increase their own odds of winning.

Despite this, there is a large percentage of chess hustlers that do not personify the stereotype of a “hustler” as they choose to earn their income with fair games of chess and even through teaching quick lessons to children and beginner players. With this positive goal behind them, the world of chess hustling has become a staple of New York neighborhoods and parks like Washington Square Park and has led to legal authorities choosing to turn a blind eye to their “illegal activities”.

The illegal nature of this culture is not limited to the present as many chess hustlers have a criminal background and played chess while serving their sentence as they believed it to be a means of therapy for themselves. In fact, chess hustling is theorized to have been mainstreamed by a former convict, Bobby Hayward, in the late 1960s as he used a garbage can to set up his stall for games which attracted the attention of media outlets and tourists.

It is important to realize that this sport has been popularized with minority groups and low-income populations, making the moniker of “chess hustler” a divisive one as it can be a demeaning definition for chess grandmasters and professionals or a badge of honor for those that aim to manipulate the game and the player for their own benefit. It is interesting to see how this challenges the history of chess as a traditionally “educated” game for those of a higher socioeconomic class as this type of “street chess” has now earned its own place on the world stage as a respectable and rewarding pastime.

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