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Answer: He loses to an opponent who bets it all. Question: What happens when David Bleich of Shearman & Sterling’s New York office appears on “Jeopardy!”? The 56-year-old finance and bankruptcy partner began watching “Jeopardy!” in the 1980s. Even while working on big deals and cases, he says that he’s managed to watch virtually every episode. Bleich tapes the show and usually watches it on the weekends. His wife and kids by his side, Bleich often blurts out the questions long before the actual contestants respond. “Everybody would say, ‘Gee, you should go on the show,’ ” Bleich recalls. In January, Bleich took the the show’s test and passed. “Jeopardy!” officials told him not to expect to appear anytime soon. But when he returned to New York from the tryout trip to Los Angeles, an answering machine message awaited him. The show wanted Bleich right away. “I felt great, my wife started screaming,” says Bleich. He taped it in February, and it aired in June. Bleich competed against a returning champion, Kevin, and Robin, a fellow contender. Only Bleich and Robin were left for Final Jeopardy. Bleich had collected $10,100; Robin, $10,500. But while Bleich earned his dollars the old-fashioned way (one answer at a time), Robin won nearly half of hers through a correct “Daily Double” response. The subject was U.S. colleges. “I had a nice conversation with myself,” says Bleich, before deciding to wager $5,000. A thoroughly prudent risk, under the circumstances, Bleich might have advised a client. Robin and Bleich both came up with the correct question: “What is Bryn Mawr?” (The question was: This college for women was founded by Joseph Taylor, a physician who lived outside of Philadelphia.) But Robin went for broke, wagering $10,000 to beat the bankruptcy lawyer. Bleich came home happy though, and with a backlog of shows to watch.

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