Weinstein, now a star hedge fund manager, was trying to get a summer job at Goldman Sachs in 1991, when he was just 18. After being told there was nothing available, he stopped in a bathroom on the way out and ran into David F. Delucia, then the head of corporate bond trading.
Delucia, who is ranked as an expert by the U.S. Chess Federation, had played Weinstein, ranked as a master by the federation, many times. He arranged for a series of interviews until Weinstein got an internship on a Goldman trading desk.
Weinstein is not alone among Wall Streeters who have a chess connection. Peter Thiel, the billionaire co-founder of PayPal, who now runs the hedge fund Clarium Capital, is also a chess master, and Douglas Hirsch, the founder of Seneca Capital, while not an expert, has become an ardent chess enthusiast.
Chess helps in trading, Weinstein said. To become a good chess player, he learned to focus on how he made decisions because he could not calculate the results of all his possible moves. Learning to deal with that uncertainty or risk has been useful. When you make an investment, “you can have an 80 percent chance of being right. And then the 20 percent comes up,” he said. “But really it is the process that you used to make the decision.”
Other games of strategy are prominent in finance. Warren E. Buffett, the chief executive of Berkshire Hathaway, is an accomplished bridge player; and David Einhorn, president of Green light Capital, who bet against Lehman Brothers in 2008, finished 18th in the main event of the 2006 World Series of Poker.
But being skilled at games is no guarantee of success. James E. Cayne, the former chief executive of Bear Stearns, which collapsed in March 2008, is a world-class bridge player, who has won many international bridge tournaments.
Still, the idea that gaming skills may be adaptable to investing spurred a hiring program in the early 1990s at Bankers Trust. At the time, the bank had a successful trader named Norman Weinstein (no relation to Boaz Weinstein), who had earned the title of international master from the World Chess Federation. In an effort to replicate his success, the bank hired a small group of people who had little or no trading experience, but were world-class chess and bridge players.
David Norwood, a World Chess Federation grandmaster (the highest ranking a player can obtain), was one of the recruits. “I was studying history at Oxford,” Norwood said. “Right out of the blue, I got contacted by Bankers Trust who said, ‘You would really make a good trader.’ I had no idea what trading was.”
Norwood took the job and was soon put on a trading desk, but it was too sudden. “It was like being stuffed into a world-class chess match without knowing the moves,” Norwood said. He quit after only a few months.
Despite the setback, Norwood said the experience “kind of planted a seed in me.” After a year, he found a job at Duncan Lawrie, a British private bank, and began learning trading and investing. In 2008, at the age of 40, he retired a multimillionaire.
Norwood said that he definitely believed that his skills in chess helped make him a success in business. “So many people in the investment world have bull-market mentalities. They do well when things are going well,” Norwood said. In chess, he said, you are constantly facing setbacks, and the people who become great players learn to overcome them.
Other companies have followed the Bankers Trust example. The website of the hedge fund manager D.E. Shaw Group lists among its employees a life master at bridge, a past “Jeopardy!” champion and Anna Hahn, the 2003 U.S. women’s chess champion.