For Jennings, it's a man vs. man competition


IBM's supercomputer adds interest, but it's Rutter - Jeopardy's longevity champ - he wants to beat



Two-game, three-night

man-vs.-machine challenge

When: Monday through Wednesday, 7: 30, p.m.

Where: CBC

As long as Ken Jennings didn't face any questions involving FedEx or H&R; Block, he knew he had a betterthan-even chance of beating a computer on Jeopardy!, not to mention downing his longtime Jeopardy! rival, Brad Rutter.

Starting Monday, Jennings will face undefeated Brad Rutter -Jeopardy's all-time money winner and one of only two players to have beaten Jennings at his own game -and the IBM supercomputer, Watson.

In the two-game, three-night, winner-take-all challenge for Jeopardy! bragging rights, $1 million in prize money is also at stake.

Jennings' 74-game winning streak, set in 2004, still stands as Jeopardy's benchmark for longevity. That streak came to an end when he tripped over a question involving the tax preparation firm: He confused H&R; Block with the courier delivery firm FedEx.

That was then, this is now. Jennings, like Rutter before him, had not stepped behind the Jeopardy! podium in five years, but he soon learned that, like riding a bike, once you've learned how to play the game, you never unlearn.

The Jeopardy! shows have been taped but no one -aside from those who were there at the time -knows the outcome.

"Honestly, I can't talk about the Jeopardy! matches now, because I have Jeopardy! snipers on the roof across the street from my house," Jennings said on the phone from his home.

Playing a computer wasn't as intimidating as it sounds, though.

Jennings says that, in all honesty, he felt more personal pressure to beat Rutter, who defeated him soundly in their only meeting before the latest Jeopardy! challenge.

"He beat me badly," Jennings said, "which was a new experience for me. To the casual viewer, this is all about, 'Can a computer play Jeopardy?' and rightly so. That's a fascinating question, and it has real-world implications. "But to me, personally, and maybe to other, harder-core Jeopardy! fans, it's also interesting to see, regardless of how the computer does, what happens next in this rivalry. I knew I wanted a second chance, and I'm sure he wanted a second chance, too."

Winning on Jeopardy! is more complicated than it looks, Jennings says. Deep down, he felt that no computer could be programmed to take all the game's nuances into consideration, even a computer reputed to be six times as powerful as Deep Blue, the IBM chess computer that fought Russian chess master Garry Kasparov to an effective draw in a dozen matches spread over 1996-'97.

Jennings knew going into the game that Watson was designed to be fast on the draw -or quick on the buzzer, in Jeopardy! parlance. Jennings saw the challenge as being akin to apples vs. oranges, rather than one Jeopardy! contestant against another. The computer's speed at responding to questions would be pitted against a human being's ability to more accurately read the wording of certain questions. A human being, Jennings reasoned, would be more adept at game play.

"Answering a Jeopardy! clue is not like performing a Google search," he said. "The overwhelming response I hear from people, when they first hear about the Watson thing, is, 'Well, of course a computer can win on Jeopardy! A computer's full of knowledge. All it has to do is just Google it.' People seem to think that winning on Jeopardy! requires a simple retrieval of single facts.

"That downplays the weird kind of mental gymnastics that do go into a Jeopardy! clue. Sometimes it is a simple matter of word association and retrieving a single fact or piece of knowledge from your brain. More often, though, there's a whole other level of thinking involved: trying to figure out which part of a clue is most relevant, trying to pick out hidden, double meanings. Answering a Jeopardy! clue is more like real-life problem-solving than it is a computer pulling a single value out of its database."

Jennings is no stranger to game theory: In 2006, he wrote the book Brainiac: Adventures in the Curious, Competitive, Compulsive World of Trivia Buffs.

Even so, he knew going in that Waton would have two big advantages.

"One, a computer has perfect recall of how it has done in every category. It's very good at computing, for example, 'This is a history question; this is a question about the Civil War; what is the likelihood I will get this right,' and then wager accordingly, whereas people play the game more intuitively.

"Secondly, a computer is not selfaware. It has a big psychological edge. I was able to win quite a few games on Jeopardy! back in 2004, just by showing up, by being the guy with the big dollar value under his name. You could see people give up right then.

"Watson is never going to be intimidated. Watson is never going to be psyched out.

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