Murrow has no varsity sports; its nationally known chess team is a source of deep pride at the school. And while Shawn’s story has echoes of the classic tale of the star high school athlete who struggles academically but remains on the team, it is also very different. Instead of marveling about quarterback options and touchdown passes, his supporters speak about castling and checkmates. And no one questions his intelligence.  Charming and funny, Shawn has a remarkable long-term memory, and parries easily with older members of the Wall Street crowd as he takes their money. He is by turns quiet and boisterous, open and defensive, and seems easily bored. He says he does poorly in English class, but he is well spoken. During nearly three years at Murrow, Shawn has missed so many classes that he is credited with passing only three courses.  Administrators and the teacher who runs the club say they have struggled with Shawn, and are seeking a balance of how to engage him in his studies without barring him from the one thing about which he is passionate. Beth Siegel-Graf, Murrow’s assistant vice principal for student guidance, said allowing Shawn to compete on the team is part of a strategy intended to keep him from dropping out altogether.  “What we try to make students and parents understand is that students doing poorly in school are hooked to the building because of their extracurricular activity,” she said. “We try to use that activity as a hinge.”  A math teacher named Eliot Weiss started the school on its road to becoming the powerhouse it is today when he formed a chess club; Murrow is now able to attract some of the city’s best young players. The team was the subject of a recent book, “The Kings of New York,” by Michael Weinreb, an occasional contributor to The New York Times. Two years ago, the team met President Bush in the White House.  Shawn, like many great players, has been blessed with the combination of an amazing visual memory and the ability to essentially see into the future by predicting various outcomes within a few seconds. During the past two years, Shawn has raised his United States Chess Federation rating more than 100 points to 2,028, giving him the rank of expert, a level just below master, and ranking him No. 19 among 16-year-olds. During that same two-year period, however, he has flunked every class.  His relationship with chess sums up his contradictions: he loves it, yet in one candid moment he said it had ruined his life. He had strong grades in sixth grade, he said, but was failing in seventh — the year he started playing. And he rejected the opinions of adults that he benefits from his relationship with the game.  “I became addicted to chess,” he said. “They think they did something for me, but they didn’t. Chess didn’t save my life. They want to make it like I’m a kid from the ghetto and I can play chess and that’s special. Why does it have to be like that? It’s embarrassing. They compare me to my environment — the way I dress to chess. You don’t have to be the brightest person in the world to play chess.”  Perhaps the most significant of those adults, Mr. Weiss has evolved into something of a father figure for Shawn, whose own father died when he was young. The teacher said he was taken aback by Shawn’s chronic underperformance.  “I have never had a student this talented in a particular skill — not just talented, but one of the best in the country — and so disinterested in schoolwork, not understanding what it means to fail high school,” Mr. Weiss said.  On some days, Shawn does attend classes with about 10 other students who are also behind. On many other days, he simply does not bother. He likes math, but the algebra course he has been forced to take repeatedly is too easy, he said, so he does not make an effort. “The sad thing is, some of the kids can’t even do it,” he said.  Murrow, a 4,000-student school in the Midwood neighborhood with a far-reaching variety of course offerings that are reminiscent of a small liberal arts college, was founded in 1974, and it gives its students considerable freedom. Periods are called bands. There are no bells, and no one is herded from class to class. Free time is scheduled into every school day, and students can choose to eat, to sleep, to do homework, to do nothing or, as Shawn has often done, to play cards in the cafeteria.  “It is a school where if you don’t have your personal responsibility together, you could drop out,” Shawn said.  Ms. Siegel-Graf, the assistant vice principal, said Shawn was allowed to accompany his teammates on the plane to Missouri on Wednesday afternoon after a conference at which he promised that, this time, he would begin going to school regularly. Shawn turns 17 on April 24 — 11 days after the nationals start — and Ms. Siegel-Graf said Shawn and the school had worked out an arrangement in which although he would still be technically enrolled at Murrow, he would begin taking courses to prepare for the G.E.D diploma.  The rules for the national tournament require students to be enrolled full time in school in the United States or its territories for the entire semester. They also state, “The coach is responsible for assuring that all of his players are properly registered and eligible to participate as members of his team.”  On a recent Thursday, a few weeks before the nationals, Shawn said he had not gone to school because he had a sore throat. Later, he said he had run out of minutes on his mobile phone and needed to win some money playing chess to pay the bill.  Here, among the businesspeople and tourists on Wall Street, Shawn sticks out with his Yankees cap, baggy jeans and well-worn red and black Nike high tops, but he also mixes easily with the stockbrokers and others who come to play.  They challenge Shawn and lose their money, even after he warns them he is an expert.  “What I do is allow them to think they can beat me,” he said, though he denies adamantly that he is a hustler. “It’s gambling, and gambling you do at your own risk.”  Playing chess for money is a gray area in the law. The state statute generally prohibits wagering on “games of chance,” but it is unclear whether chess falls into that category. A Police Department spokesman did not respond to a request to clarify the matter.  Shawn was taken away from his birth mother when he was one week old because of her crack cocaine habit. Lidia Martinez, a widow who is Shawn’s adoptive mother, said she knew immediately upon seeing the week-old Shawn that she wanted to adopt him. Ms. Martinez acknowledged however, that she, like everyone else, had failed to get her son to go to class. “He believes he’s too smart for school,” she said.  Shawn says he is able to remember his biological father, who died when he was 2. He says he can even recall his own first birthday.  At Murrow, Shawn is the third best chess player, behind the seniors Alex Lenderman and Sal Bercys, who are each among the top 2,000 players in the world. They were both featured prominently in Mr. Weinreb’s book, while Shawn appeared in fewer passages. In one he is described as being “monosyllabic” and unable to let his guard down.  “The kid’s been an enigma since junior high school,” Mr. Weinreb wrote. “He has a gift, that much is clear, and he’s managed to discover it amid a life that has been fraught, like so many in the city, with disappointment.”  While Alex and Sal have played since around the time they started kindergarten, have had private coaches, and have extensive experience at tournaments, Shawn claims to have never even cracked a chess book. “I never studied a book in my life,” he said. “I’m too bored.” Shawn said he learns by playing, often against opponents online. He favors an aggressive style that employs his pawns as attackers.  “When you put pawns together, there’s no stopping them,” he said. “You put two or three together and they practically control the whole game. People know me for my pawns.”  A version of this article appears in print on , on Page A1 of the New York edition with the headline: At 16, a Star at the Chessboard, But Adrift in School and Life. Order Reprints| Today's Paper|Subscribe
A chess star at a Brooklyn high school skips a lot of school — but he is no ordinary truant.