Pawns of the Game

Love, obsession, madness, and other matters of chess

Omar Cartagena favors the Ruy Lopez. He admires the clean simplicity of the opening line, allowing him to ponder the various offshoots he could take, the alternative paths toward total domination. In top form, Omar figures he can imagine about a hundred different moves simultaneously, so he's ready for his opponent's every response. There's a reason he's the highest-ranked chess player in S.F.

Sometimes, though, Omar looks up from his board and wonders what the hell he's doing, sitting out in the rain on Market Street, sharing space with a few dozen nobodies, hustling games for $5 a pop. These are the occasions when the line isn't so simple, when life keeps coming up with unexpected countermoves. It all seemed so much clearer back when he was a proud member of the Philippine national team, back when the government paid his way so he could compete in the prestigious U.S. Open in the summer of 1995. Omar placed sixth in the tournament. He met a woman. He never returned to his Cebu home.

Now he calls S.F. home. Aside from being the city's best player, Omar also is apparently the only person who makes a full-time living from playing chess. Ask around at the Chess Club in the downtown Mechanics Institute, or among the studious enthusiasts at the Horse Shoe Coffee House in the Lower Haight, and they'll be at a loss to name another player who doesn't hold down a day job, or have some gig on the side that helps pay the bills. Omar, it seems, is the only one.

But it isn't easy. Because of his ranking, Omar is flown by organizers to tournaments around the country, and he often wins. This brings in a few thousand dollars a year. He gives lessons every now and then. This brings in a few hundred. But it's the hustling on Market Street that's Omar's bread and butter. This is blitz chess, with both players blazing through their moves in just five minutes, stopping and restarting the clock every few seconds. On a good day, Omar can squeeze in about 40 games -- and if he swings $5 wagers on a quarter of them, he can pocket a cool 50 bucks.

They all know Omar on the street. They know he can beat the pants off any one of them any time he pleases. So Omar handicaps himself by giving himself only one minute in which to make all his moves. He still usually wins.

"If he had the resources to play in more tournaments, instead of wasting his talents down there, he could be a top-flight player," says Max Wilkerson, who stepped down last November after 16 years as head of the San Francisco Chess Club. "He's too poor to devote himself to high-class chess." Nevertheless, Wilkerson readily concedes that Omar is the city's strongest player.

"He's an excellent player," agrees Walter Shipman, an international master who relocated to S.F. after decades as a leading figure in New York's chess community. "Cartagena is a very determined, aggressive player."

Berkeley grandmaster Walter Browne, six-time U.S. champion and the player in the Bay Area rated highest by the U.S. Chess Federation, admits that Omar is "pretty talented" and "a very good tactician." But Browne is reserved in his praise for Omar's abilities, in part because they haven't played many games, and in part, possibly, because Omar whipped Browne in a recent tournament.

As for the criticism of his street play, Omar, a stocky fireplug of a fellow, is unfazed. "If you play only for money, you are not really playing," he says in halting English. "You should play because you love chess."

It would be better, of course, if his wife, Josie, a Filipina who is now a U.S. citizen, agreed. But Josie doesn't see chess brilliance as a sufficiently good excuse for not holding a real job, not when they've got two daughters at home from her first marriage, and not when her mother also shares the apartment. Omar, 32, tries as best he can. He puts off his chess studies until after Josie goes to bed at night. He tries to be home to look after the girls if Josie is going out. But it's hard. "It's difficult to support a family," Omar confides.

By comparison, the Ruy Lopez is a snap.

What is it about chess? People don't forsake friends and family for a good game of Scrabble. No one has been famously driven to the brink of insanity by Monopoly or Clue. But chess -- well, ask serious players and they'll insist that it's not just a game. It's a sport. It's an art. It's life itself. And to be very, very good at this whatever-it-is, a person has to make sacrifices.

It's no exaggeration to say that the world of the serious chess player is one of such narrow focus as to butt right up against obsession. Chess requires study, it requires patience. It requires a single-mindedness that leaves little room for much else.

At the beginning of the century, a young American named Harry Pillsbury earned a meager living by playing simultaneous games of chess -- his record was 22 -- without looking at any of the boards. To make the feat all the more interesting to onlookers, he would at the same time play a hand of whist and memorize lists of words shown by the audience. When Pillsbury died in 1906, the New York Times attributed his demise to "an illness contracted through over-exertion of his memory cells."

Good chess players are like that: extroverted, bold, highly intelligent, perhaps more than a little loony. It's almost required in order to excel at a game that's been pondered to extremes since the sixth century. Not much room remains for genius in the chess world. In a finite realm of 64 squares, only so many moves, so many variations can be devised. Yet they keep coming, the top players, trying to peer deeper than others, trying to find that one, pure combination that will take the game to places no one has seen before.

Omar played in his first tournament at the age of 12. He won. "It was the only sport I could be competitive at," he says. "I tried basketball. I tried boxing. I wasn't good enough for them." But he was a natural at chess. "Nobody taught me how to play," Omar says. "I taught myself."

His father, like his future wife, didn't see how anything could come of devoting all his energy to a board game. He wanted Omar to grow up and be an engineer. They fought, and Omar threw himself at his schoolwork to pull in the high grades that would appease his dad. But he never turned his back on chess. "I could read chess books and remember all the moves," he says. "All of them."

He went to college for a year, but it was quickly apparent that his aptitude lay elsewhere. In 1984, after once again crushing all the competition in a local tournament, Omar was named Cebu's outstanding athlete by a Philippine newspaper. Two years later he helped bring the national team to a respectable sixth-place finish at the world chess Olympiad in Dubai.

Then, his father's displeasure ringing in his ears, Omar tried for the first and only time in his life to walk away from the game. He landed a job with a food-processing company, where he passed four uneventful years looking after canned goods. He didn't play once. "I can only concentrate on one thing at a time," Omar explains.

In 1990, a friend called from Manila to request Omar's help in organizing a tournament. Omar arrived at the venue and took in the rows of chess sets, the clocks, the battles waiting to be joined. "I quit my job at the food company and started playing again," he says. "I missed the action."

In 1993, Omar placed second in the Philippine Open and was acclaimed one of the country's top players. It was only natural that the government would spring a couple of years later for his airfare so Omar could defend national honor at the U.S. Open, held that year across the bay in Concord. They never anticipated he'd like the level of competition in America so much that he wouldn't bother returning home.

Omar shrugs and says a little eccentricity is common among talented chess players. "Bobby Fischer was eccentric," he offers by way of explanation. "Fischer is my idol. He was a genius."

Such a genius, in fact, that Fischer played in his first tournament at the age of 10. Four years later he traveled to S.F. and won the U.S. Junior Championship, and a year afterward he became the youngest ever grandmaster and U.S. champion. The rest is pretty well known -- the 1972 world championship against Boris Spassky in Iceland, the years of reclusiveness, the return to semipublic life (and interest in anti-Semitic causes), the violation of an embargo on traveling to the former Yugoslavia, which means he'd face criminal charges should he ever now return home from his expatriation.

It's a short hop from genius to madness. For some, like Omar, the insanity is kept at bay by the continuing pursuit of excellence. For others, the only recourse is to flee.

Jay Whitehead was 15 when he looked across the chessboard and saw the person he would never be.

It was 1977, and Jay, one of the world's top-ranked players his age, was chewing up the competition in the under-17 chess Olympiad in France. But the 14-year-old boy he faced now was different. He was from the Soviet Union, for one thing, and everyone knew that the Soviets were the leading force in international chess. Fischer had said the Soviets fixed matches among themselves so as to allow the strongest players to glide easily to the finals, and grandmaster Viktor Korchnoi confirmed that game-rigging was common among top Soviet players. But there was something else: a quiet fierceness in the boy's eyes and manner. "Just from sitting across from him, you could tell there was something extraordinary about this person," Jay recalls. The young Soviet, barely out of puberty, was Gary Kasparov, who now reigns as world champion.

"The game was boredom personified," Jay says. "He played a dull opening, and I strived to equalize. There must have been some apprehension. I was afraid to duke it out with him. Maybe he was also a little afraid of me."

The game ended in a draw, but it was enough for Jay to score 8.5 out of 11 points in the tournament and finish second; young Kasparov's eight points brought him in third. Where the two boys differed, though, was that Kasparov returned home and resumed the intense study that would make him one of the most knowledgeable and well-rounded chess players in history. Jay, on the other hand, would study a bit, but not with any great zeal to push his game to new limits.

"I just played for the sheer thrill of winning, and the artistic pleasure of creating something logical on the board," he says. "I never really thought about being world champion. I knew that to get better would be hard work."

Jay chooses his words carefully, as if a conversation with a new acquaintance requires as much cunning as a well-executed King's Gambit. It's difficult in any case to believe that a person who was once among the 12 best players in America, who won the U.S. Junior Invitational in 1981 and the chess Grand Prix in 1987, did not think about becoming world champion. A chess player, after all, is a person whose natural inclination is to think many moves ahead. A chess player is as involved with future possibilities as with present realities. Outcomes are planned, not awaited.

It's more likely that Jay thought quite seriously about becoming world champion, but understood, as he says, that scaling this particular peak would be hard work indeed. This is where one of Jay's personal demons lives: in his apparent fear of committing himself to being the best. Jay Whitehead, who claims an IQ of 176, advanced as a chess player through raw, brute talent. For him, it was always effortless. To make a special effort, therefore, would be to expose himself to the possibility that, at his very best, he might not be good enough.

This is where Jay's other demon lives.
"I would get extremely depressed over losing games, to the point where my whole world would collapse," he says. "This was something that really stunted my development, the way I would react to setbacks. My tendency was to become angry. I wouldn't learn from my mistakes. I suffered a lot."

To ease the suffering, Jay turned to religion. Since 1984 he has been a Hare Krishna devotee. Around the ornate confines of the International Society for Krishna Consciousness in Berkeley, he is called Jaya Krishna, and his unique abilities as a chess player are mostly unknown to others. When he excuses himself from lunch by saying a reporter has come to interview him, a man with a yellow stripe on his nose looks up from the floor and asks why. Jay explains, slightly embarrassed, that he used to play chess, that he was once pretty good.

Jay is now 35. Like many vegetarians, he looks like he doesn't eat enough. A misbuttoned shirt and a rubber band serving as a watch strap hint at a lack of interest in personal appearance.

Jay learned to play chess 30 years ago, first being taught the basic moves by his father and then pursuing it on his own -- as many kids did -- amid the hoopla over Fischer wresting the world chess crown from Spassky. Sales of chess sets and chess books skyrocketed in the United States, and chess enjoyed a status among Americans higher than any other time before or after. For Jay, it was just the beginning.

"Chess became my purpose in life," he says. "It gave me a focus, something to care about." This was helpful, because Jay's parents had been roaming Europe, teaching at American military bases, and Jay was feeling adrift and isolated. "Once I got back to San Francisco in 1973," he says, "chess became an obsession. It became a substitute for the natural urge to find meaning in life."

Most of all, it became a way he could cream his brother. Paul Whitehead, who is a year-and-a-half older than Jay, also learned chess from their father, and had been similarly captivated by the excitement surrounding Fischer becoming world champion. "He was always a little better than me," Jay remembers. "Then, around the early '80s, I started having better results."

The brothers were never all that close. They fought a lot, and engaged in the can-you-top-this sniping common to many siblings. "Chess was the most intense aspect of our rivalry," Jay says. "It was intolerable to be the loser. It was the ultimate humiliation." The brothers seldom see one another these days, and Jay says he's pretty much sworn off chess for good. But he's said that before.

In 1987, after losing four in a row in an important tournament, Jay told himself he couldn't take it anymore. The pain -- the humiliation -- was too severe. Losing left him battered and scarred, vulnerable to the dark forces within that no amount of Hare Krishna chanting would chase away. "I had to give it up out of necessity," he says. "It became too much of my psychological makeup. It became like a drug."

Jay shuts his eyes tight, as he has done frequently in formulating careful answers to my questions. He is playing a private game somewhere inside, working out the moves, trying to gain the upper hand. "There's nothing wrong with chess," he concludes. "But for a chessaholic, there is."

A few months ago, out of the blue, Jay decided to enter a two-day tournament in Sunnyvale. He doesn't really know why -- maybe just to flex his muscles a little, see how he'd fare against the new talent. Maybe because he had no choice. "I thought it would be easy," he says.

Jay won his first two games. They weren't pretty wins; he had to use his instincts and experience to overcome stupid blunders. Then, in his third game, he got whipped. "I felt totally confused and depressed," he says, his face darkening. "I still do."

Somewhere deep within, one of Jay's demons has removed another piece from the board.

"My brother was exaggerating," Paul Whitehead says over coffee at an Irving Street cafe. "I've seen him play in lots of tournaments, and I never saw him act humiliated." Later in our conversation, though, he says Jay may have been telling the truth about the intensity of his emotions. "If you're a competitor in any sense of the word," Paul decides, "you must feel all those feelings."

Paul is such a competitor -- and he isn't. Like his brother, Paul was a powerful chess player as a teen-ager. He tied for first place in the under-21 U.S. chess championship in 1978, and won the American Open tournament the same year. He was, by his own estimate, among the top five players his age in the country. Then, at the age of 18, it all changed.

"I woke up one morning, and I just wasn't that interested in the game anymore," Paul says. "To go farther would have limited myself in other ways. I saw the involvement that people needed to get to the top."

I observe that Jay said almost the exact same thing -- that he was unwilling to make the effort necessary for advancement at the top levels. Paul cups his chin in his hands and considers momentarily.

"It's not that," he replies. "It was more that I didn't really like a lot of the other players. I didn't like the rampant egotism in terms of how strong you were as a chess player."

Paul gives an example. He recalls the time he beat a friend at a Berkeley cafe, and how a prominent grandmaster joined them afterward as they analyzed the game. "The grandmaster then says to my opponent, 'Why do you play games with these weak players?' like I'm not even there." Not long after, Paul had the satisfaction of trouncing the grandmaster at a major tournament. And, Paul admits, the win was very sweet indeed.

"The whole thing of intimidation, one-upmanship, underhanded dealing -- it's all really common to stronger players," he says. "There's winning and losing -- nothing else. The most important thing is checkmating your opponent."

Paul seems to have come to terms with whatever inner demons reached out for him from the chessboard. He's been married for several years now and has two kids. He works as a free-lance photographer, and makes an engaging impression with his playful smile and wavy, Kenny G-ish hair. He says he's always been well-adjusted socially, with none of the alienation and loneliness frequently associated with being a chess prodigy. "I had friends," he says simply enough.

(Jay, by contrast, says he was "basically confused" as a child, especially in his dealings with girls, which he found lacked the "purity of logic" of a good game of chess. "I didn't have any friends," he says. "All my friends were older chess players.")

For Paul, chess was a stepping stone in his life, nothing more. Although he was one of the best young players in the country, when he saw that chess was taking up too large a space, he pulled back. "I still play," he says. "I also still play basketball, and Go. And these days, the game I play most around the house is Candy-land."

Paul believes he has the will to win as a photographer that eluded him as a chess master. This time, he insists, he's committed to succeeding. "I'm a much better photographer than I was a chess player," he says. "I have more of an interest in it. I apply myself to it.

"But," he adds, "one day I may wake up and decide I've lost all interest in photography."

To the unknowing, Omar appears perfectly ordinary in a gray baseball cap and blue sweat shirt. We're standing on Market Street watching a couple of games in progress. The regulars know better, and treat Omar with the deference of royalty. They nod to him and hope for a sign of recognition in return. Omar stands with his arms crossed, master of the universe.

The better street players aren't the ones gathered near the Powell Street cable car terminus. Those are the hacks. The better players are down the street on the next block. For the most part, they're Asians and Russians, and they turn out rain or shine to match wits and maybe score a few bucks.

Omar says he hangs mostly with the good players, but goes slumming among the others when in search of fresh prey. There are always a few around cocky enough to take up his five-minutes-to-one challenge. They always lose.

"I want to be a grandmaster one day," Omar says. "As a grandmaster, I would be invited to all the important tournaments and receive appearance money for participating. If I was a grandmaster, I would not play on the street."

He savors this dream, and then a friend sidles up and tells Omar his wife is looking for him. Omar's bubble pops, and he glances around nervously. He spots Josie approaching down the sidewalk. She looks pissed.

"Listen," Omar whispers, "I have to go. Sorry. Maybe we can talk some other time."

And the king falls in step behind the queen.

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