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Yale-Bound Hess Seeks U.S. Chess Title as Wall Street Beckons

Yale-Bound Hess Seeks U.S. Chess Title
Robert Hess, chess grandmaster in competition at the U.S. Chess Championship in St. Louis. Source: Chess Club and Scholastic Center of Saint Louis via Bloomberg

Robert Hess, who interned at a hedge fund in 2008 and will attend Yale University in August, will try to see the future over the next seven days -- on a chessboard.

The 19-year-old grandmaster is alone atop his group in the first phase of the 2011 U.S. Championship in St. Louis, and has clinched a spot in the semifinals. In five months, he plans to use his chess skills to help study finance at Yale in New Haven, Connecticut, and join the likes of Harvard University economics professor Ken Rogoff as grandmasters to attend the university.

“These are the kinds of things that I like doing, strategizing and finding patterns,” Hess said in a telephone interview from St. Louis.

Hess, who deferred from Yale for a year to play chess full time, worked a 2008 summer internship at Fortress Investment Group LLC, a New York hedge fund. At Fortress, Hess analyzed entertainment stocks and developed an interest in finance.

“It is something that I want to study in college, and this internship really opened my mind to it,” said Hess, who is from Manhattan and was captain of the Stuyvesant High School football team as a sophomore.

He said finance is similar to chess, in that success depends on the ability to see the effective move out of a wide range of possibilities.

Grandmaster Capital

Patrick Wolff, a former Yale student and Harvard graduate who won the U.S. Championship in 1992 and shared the honor in 1995, worked at Peter Thiel’s Clarium Capital Management LLC before launching Grandmaster Capital Management LLC on Jan. 1. Wolff says his chess background helped him make the transition into business.

“There is a quality of mind that comes from chess, in terms of thinking analytically and conceptually,” Wolff, 43, said in a telephone interview.

Grandmaster Capital is a five-person hedge fund with about $50 million in assets under management. Wolff, who plays six simultaneous blindfolded games each year at Warren Buffett’s Berkshire Hathaway Inc. annual shareholders meetings in Omaha, Nebraska, says chess has also helped him network in the business world.

“Throughout my career there have been many moments where my chess experience has gotten me noticed or helped me make connections,” Wolff said.

Hess, like Wolff, started playing chess at age 5, and can remember losing in four moves in his first competitive tournament. In 2001, at age 9, Hess won the K-3 SuperNational title, and eight years later placed second at the U.S. Championship. He became a grandmaster, the highest permanent title that can be earned from the World Chess Federation, in 2009.

‘Stormed Field’

“Robert was ranked 17th in a field of 24 players that year, and wasn’t even a grandmaster,” Tony Rich, director of the Chess Club and Scholastic Center of Saint Louis, said in a telephone interview. “He came in as a dark horse and just stormed the field.”

Hess graduated from high school last year and planned to go directly to Yale until he won the Samford Chess Fellowship, a $42,000 grant that’s helped pay for coaching and trips to tournaments in Russia, Spain, Greece and Iceland.

“Technically, chess is a job for this year,” Hess said. “If it becomes a chore, then it’s no longer fun, but I still love every game I play.”

The 2011 U.S. Championship, which has competitors ranging in age from 15 to 54, started on April 15 and runs through April 28. Hess has four wins and two draws against his first six opponents, and will advance to the two-day semifinals, which start on April 23. Hess has won his last four games, all against higher-ranked opponents with a combined eight U.S. Championship titles.

"He Plays Calmly"

“Robert plays much more maturely than you expect from someone his age,” Rich, 29, said. “He plays calmly, he doesn’t try to crush his opponent at the opening and he is able to out-play them from there.”

The tournament has a $250,000 purse, with the champion taking $40,000. Rich said the prize fund has grown from $50,000 in 2008.

Last fall, Hess was invited to play exhibitions outside New Meadowlands Stadium during New York Jets home games. Hess played 25 simultaneous games against all comers, with new players sitting each time a game ended. He never lost.

Hess says chess has taught him lessons about independence and responsibility.

“In chess you learn from your mistakes, and if you don’t learn, you’ll lose again in a similar fashion,” Hess said. “That’s true of pretty much everything in life.”

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