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Roger Craig: Jeopardy's most devastating player

Roger Craig became famous for making bold moves on Jeopardy that paid off big, notably for breaking Ken Jennings' one-day record, but he is also one of the game's canniest strategists.

Data mining and text clustering

Now living in Brooklyn and working as a data scientist, Craig became famous for how he prepared for the show. Instead of studying wildly, he downloaded all the game compiled at j-archive.com and used his data training to parse the questions and categories and look for patterns.

For example, more serious "academic" categories tended to appear in the second round (the Double Jeopardy round), while sports, for example, tends to come up in the first round (the Jeopardy round).

In fact, work on the app began well before he even auditioned for the show. "It was very organic, so at first all I was doing was looking at the categories: seeing how often does 'Presidents' comes up as opposed to'Shakespeare,' for example, then I'd put it aside for a few weeks before adding to it."

As friends starting going on the show, he tailored his app for them, which allowed them to "play" old games. But since players only have a few weeks separating The Call and the taping, Craig realized that he'd need to maximize his use of it before even auditioning.

Filling in the gaps

The app helped him refresh on what he'd known already and pointed out many of his weaker spots, and in particular weak spots with a solid chance of coming up, like European royalty. So he did a Sporcle quiz on Danish monarchs, noticing that for 400 years they alternated between kings named Christian and kings named Frederick. That came up. In Final Jeopardy. "I almost thought I was dreaming when I saw that."

On the other hand, he knew that kids' books and contemporary literature were weak areas. With time to kill before the show, he wandered over to a mall near the Culver City hotel where most Jeopardy contestants stay. He found a Barnes and Noble and saw Ian Falconer's Olivia the pig series on a display. That came up.

"A lot the big winners have played in quiz bowl or been in the trivia world, so it's not like they say, 'Oh, I want to be on Jeopardy' and then they learn everything," he says. "You're filling holes so you're more ready for the 5-10 new things that come up over the show."

He thinks of it as a conditional probability. "It's not the probability it comes up, given that you studied it, which you shouldn't worry about, because that will be low. Instead it's the reverse: it's the probability that you studied it, given that it comes up."

The $77,000 Game

All this worked paid off, particularly when he broke Jennings' one-day record in 2010, in only his second appearance.

It was an unusually strong game. Going into Final Jeopardy, he had $47,000. "I wasn't thinking of the record at all during Double Jeopardy, I was just maximizing my score."

One of his opponents had a negative score and the other was far behind. Not only was it a locked game, but he had enough room to make a huge bet.

Although you don't see it on air, Alex Trebek mentioned to the audience that Craig was in position to break the record. He'd already known: his opponent had turned to him and said, "Dude, I think you can break the record."

As Craig recalls: "I hadn't even looked at the scores yet but then I did and I said, 'I think you're right'"

It was an easy decision. "Well, I have a chance to break the record and even if I'm wrong, I still come back the next day. You gotta try for it. After the first game everything you win is gravy, so I thought of it like poker chips instead of money. The only thing might have stopped me was if the category were Things Roger Knows Nothing About but even then you might take a flyer on it. It's not just the money, it's also the intangible benefit of being the guy with the highest game ever. In some ways that might be worth more than $30,000."

He wagered $30,000 on Literary and Movie Title Objects. "It seemed sort of narrowed down a bit and you can start brainstorming answers: Maltese Falcon, Harry Potter objects. It's going to be a famous book and a famous movie. There are only so many things that fit the bill that Jeopardy would ask about."

As it happened, he knew the answer (Bridge on the River Kwai) right away. "I was thinking, 'How am I going to celebrate? Should I jump up and down? What do I do?'"

Ken Jennings was out of town when the shows ran, but blogged about it and congratulated Craig by email. He later let Jennings use his app to prepare for Watson. They also talked by phone.

"If it were still, say, Jerome Vered's record, it wouldn't have gotten a hundredth of the publicity. Nothing against Jerome or anyone else, just that when it comes to Jeopardy contestants in the public's mind, there's Jennings and then there's everybody else. And it was my second episode, so everybody was saying, 'Is this the new Ken Jennings?'" The AP story brought everything back down to Earth. "As I recall, it ended with something like, 'Roger still has to win 72 games in a row to tie Jennings' record streak.'"

Doubling Double Jeopardy

In his seven-day run he amassed $231,200, still one of the five highest regular season Jeopardy scores of all time, as of 2013. This earned him a berth on the Tournament of Champions, and he progressed to the two-day final, where he pulled off another historic feat: hitting two straight Daily Doubles, going all in each time.

Part of his lucky break was guessing where the Daily Double would be and hunting for them. "The first column is really likely and it's more likely you find Daily Doubles in the bottom half of the board. Of course I didn't know where they are. When you get the first one, you can make an educated guess where the other one is. It was mostly dumb luck."

Either way, first he bet and won all $9000 and successfully identified Anne Bronte as the author of the book Agnes Grey. He then hit another DD and bet all $18,000, winning when he knew that Dutch and Sranan Tongo are the main languages of Suriname.

"When I got the second Daily Double, I thought if it made sense to go all in the first time, why not go all in for the second one. " But he was also aware of the potential psychological impact of the risk he was taking. "No matter who you're playing you want to put the game away as soon as you can."

Even though he was playing Tom Nissley, who had passed him on the all-time winnings list, Craig was still thinking strategically. It was early in the first game of a two-game final. He calculated that even if he were wrong on the second Daily Double, there were enough clues, and enough potential money, still on the board for him to catch back up.

"You just have to have confidence and go for it."

The $18,000 "true Daily Double" remains a record, as does his first five-day total of $195,801 (although for complicated reasons you can say that Frank Spangenberg "did more with less money").

As for the app that started it all, Craig is still interested in finding partners to help commercialize it.