For Love or Money: The World of Chess Hustling

By: Steve Scott
Source: OnStage Magazine

They can be found in any of New York’s public parks or gathered in chess shops throughout the city. Their names evoke the legendary status that some of them achieve: Broadway Bobby, Russian Paul, Sweet Pea, Poe. Their ranks have included future Hollywood greats, day laborers, students, international champions and homeless knockabouts. Although the trade that they ply is technically illegal, they are largely ignored by legal authorities—and their unique brand of fame has been chronicled by newspapers, blog sites and at least one feature film.

Welcome to the world of chess hustlers, players who compete at the board game for money, a fixture of New York street life that has been referred to as the “largest growth industry” in the city. Chess hustlers have plied their trade in Manhattan’s parks for decades; according to local lore, actor Humphrey Bogart made his living as a master of speed chess during the Depression, as did future Unites States chess champion Arnold Denker. Film director Stanley Kubrick (whose passion for the game made its way into such movies as 2001: A Space Odyssey) was a frequent—and victorious—habitué of Washington Square Park’s chess boards in the early 1960s. But the popularity of street chess is generally acknowledged to have started with a former convict named Bobby Hayward, who in the late 1960s or early 1970s set up shop on a garbage can on Eighth Avenue, between 42nd and 43rd Streets. Word soon spread, and Hayward’s enterprise was immortalized by photographs in The New York Times. Such mainstream attention brought visibility (and perhaps legitimacy) to Hayward and his fellow hustlers, and soon street chess was a sought-after activity for both chess wizards and New York tourists.

The form of the game preferred by most hustlers is known variously as speed chess, blitz chess, or lightning, in which each side has five minutes (or three, in a variation known as bullet chess) to complete all their moves. There are two ways to play speed chess: touchmove (meaning that if a player touches a piece, he has to move it) or the more common clock-move (meaning that a move is not complete until a player punches the clock). Veteran speed chess players can keep several games going at once, keeping track of the tally as they go. This can be an effective method of bilking more money out of the neophyte player by causing him to lose track of the number of games that have actually been won, or to lose track of the amount of the wager made on each game. There are other tricks that the hustler can use to fix the outcome of a game: rigging the clock so that the opponent’s time runs out faster than the hustler’s or, when a hustler’s luck runs out, fleeing the game via an unannounced break. In his 2000 book The Virtue of Prosperity, author Dinesh D’Souza describes one such game in which his opponent, a storied street chess champion, was unexpectedly down after fifteen minutes. “I’ll be right back,” the opponent said, heading for the men’s room in a hotel across from the park. A few minutes later, an observer pointed out the obvious to D’Souza: the hustler wasn’t coming back, and D’Souza wasn’t getting his five-buck winnings. Although such shenanigans are eschewed by many bona fide chess hustlers, the competition among hustlers is fierce, and the stakes may be higher than the monetary bet at hand. As the character Flash in Cándido Tirado’s Fish Men says, “We’re not happy with just winning. We want to obliterate the opposition.”