Biggest winner

The biggest winner in chess, last year, was Ylon Schwartz, 38, a FIDE Master who grew up in Brooklyn, New York, an uninspired student who took on odd jobs after flunking out of college. As a public school special education assistant he started playing chess for a few dollars on the side, and soon was hustling $100 per day playing chess against passersby in Manhattan's Times Square. He soon devoted full-time to gambling on backgammon, chess, darts and horses. An inveterate gambler, Schwartz made $340 from passersby on wagers that he would be able to throw a lemon across a street onto the top of a Burger King restaurant on the other side. Schwartz had practiced the throw the previous night and knew he could win the bets.

Schwartz was introduced to poker – specifically to Texas Hold'em – by Fat Nick, a fellow backgammon player. He entered a pair of poker tournaments at a club run by Fat Nick in 2000, winning both and walking away with $12,000 and a new passion. Soon he stopped playing competitive chess and devoted himself almost entirely to poker.

Schwartz has drawn comparisons between his tournament experience as a ranked chess master, noting that many of the skills he needed to succeed in chess are useful in poker and that the memory skills needed in chess transfer to retaining details on betting patterns of opponents needed to win in poker. He also pointed out that chess strategy provides excellent preparation for knowing when to time bets to prevent other players from folding when he has a good hand. Schwartz observed that the two games share the geometric relationships between the pieces on the chessboard and those connecting the cards and chip stacks of fellow poker players, while recognizing that chess is a game of complete information, in contrast to poker.

In November 2008 Ylon Schwartz, whose nick in poker is TenthPlanet, made it to the final rounds of the World Championship No Limit Hold'em Main Event of the 2008 World Series of Poker (WSOP). He was was eliminated on November 10th after going all in against Peter Eastgate and ending the tournament in fourth place, earning $3,774,974.

Souce: Wikipedia. See also profile in PokerPages.

Biggest loser

Born to Israeli and Polish émigré parents, Boaz Weinstein – haven't we heard that name before in chess? – was enrolled in chess workshops at the age of five by his parents. He was was a chess master by 16, and also excelled excelled at poker and blackjack. He became a top trader at the Deutsche Bank, where he collected similar-minded colleagues around him, and would play high-stake poker with them after the trading day was over. In 2005 he won a Maserati in a poker tournament sponsored by a unit of Warren Buffett's Berkshire Hathaway Inc. Weinstein also played blindfold chess, once against a Russian colleague, whom he beat in two hours of play, with over 100 colleagues watching.

As a derivatives trader Weinstein was a legend on Wall Street, taking home annual bonuses of about $40m. His signature trade was a strategy called "capital structure arbitrage," based on gaps in pricing between various securities of a single company. For instance, if he thought its bonds were undervalued relative to its stock, he might take bullish positions on the bonds and simultaneously bet against the stock, waiting for the disparity to shrink or vanish.

The Deutsche Bank profited from Weinstein's financial wizardry, but the instruments were questioned by economists, who think the market became little more than a casino, one with $60 trillion of bets outstanding at its peak last year. The enterprise collapsed in September when one of the biggest gamblers, Lehman Brothers, went bust, and Weinstein's charmed position began to decay. Losses spiraled to $1.8 billion, wiping out two years of profits and shredded the reputation of Germany's most powerful bank. On Thursday the German bank reported a 2008 loss of $5 billion (€3.9 billion), its first one-year loss in over five decades. Deutsche Bank shut down Weinstein's operation and wound down many of his positions. He left the bank this week, with plans to start a hedge fund.

Links and sources

• Wall Street Journal: Deutsche Bank Fallen Trader Left Behind $1.8 Billion Hole
• Independent World: Exposed: chess genius who lost his bank $1.8bn