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By Root 345 0

was his undoing. He faced Matt Martin, a police officer from Arlington, Virginia, and Jelisa Castrodale, a sportswriter from North Carolina. Just a day earlier, his luck with Danish kings and atomic elements made him wonder if he was dreaming. Now his fortunes took a cruel turn. Sleep-deprived, he found himself struggling in a category that seemed to be mocking him: “Pillow talk.” Such fluff was hardly his forte. Castrodale identified the “small scattered pillows also known as scatter cushions” (“What is a throw pillow?”) and the “child carrying the pillow in a wedding procession” (“What is a ring-bearer?”). And when a clue asked about “folks with tailbone injuries” sitting on “pillows in the shape of these sweet baked treats,” Martin buzzed in. It was the cop, as Alex Trebek gleefully noted, who answered, “What are donuts?”

Barely a week before Craig’s final show aired, Watson was engaged in a closely fought match with the former champion Justin Bernbach, and they were playing the very same clues. This was the day that Watson, following a dominating morning, later faltered and crashed. Its patterns in this game seemed to mirror those of Roger Craig. Like Craig, Watson appeared largely lost on pillow talk. Both of them, however, swept through the category on the ancient civilization of Ur. (When you have a category like that, Craig later explained, “You almost know the answers before they ask the questions.” He listed a few on the fingers of one hand: Iraq, Sumeria, Cyrus the Great, and Ziggurats (the terraced monuments they built). “What else can they ask about Ur?” Watson, though following a different logic, delivered the same winning results. Watson and Craig also thrived in the category “But what am I?” It featured the Latin names for certain animals, along with helpful hints, alerting players, for example, not to confuse “cyanocitta cristata” with Canadian baseball players (“What are Blue Jays?”). These were easy factoids for computer and computer scientist alike.

As Watson went into Final Jeopardy on that September afternoon, it held a slim lead over Bernbach and a comfortable one over Maxine Levaren, a personal success coach from San Diego. But it lost the game to Bernbach, you might recall, by missing a clue in the category Sports and the Media. It failed to name the city whose newspaper celebrated the previous February 8 with the headline: “Amen! After 43 Years, Our Prayers Are Answered.” The computer had only 13 percent confidence in Chicago, but that was higher than its confidence in its other candidates, including Omaha and two cities associated with prayer, Jerusalem and the Vatican. In retrospect, Watson was scouring its database for events dated February 8. But the machine, raised in the era of instant digital news, ignored the lag at the heart of traditional paper headlines: Most of the events they describe occurred the previous day.

Like Watson, Roger Craig reached Final Jeopardy clinging to a narrow lead, $22,000 to $19,700, over Jelisa Castrodale. The Sports and the Media category looked perfect for the sportswriter. But Craig was a fan as well and a master of sports facts—especially those concerning football. The same clue Watson had botched, featuring forty-three years and answered prayers, popped up on the board and the contestants wrote their responses. After the jingle, Alex Trebek turned to them. Martin, who lagged far behind, incorrectly guessed: “What is Miami?” Castrodale was next: “What is New Orleans?” That was right. She had bet all but one dollar, which lifted her to $39,339. Craig had anticipated her bet and topped it: He would win by $2 if he got it right. But his answer was 840 miles off target. The six-time champion, who had trained himself with the methods and rigor of computer science, came up with the same incorrect response as his electronic role model: “What is Chicago?”

Was the melding of man and machine leading Craig and Watson through the same thought processes and even to the same errors? Weeks later, sitting in IBM’s empty Jeopardy studio, David Gondek opened his Mac and