Arthur Chu has recently won money and attention for doing something on Jeopardy! that even Watson didn’t attempt: gaming the system–hacking it in a sense. IBM’s robot beat the humans the old-fashioned way, never using out-of-ordinary strategy to circumvent the spirit of the game or disrupt it. Contestant Chu has done just that. For instance: He pursues Daily Doubles he knows he can’t answer, betting a miniscule amount on them, absorbing a nominal loss and scrubbing them off the board so that the other players can’t gain from them. And that’s just one of his “tricks,” all legal if unorthodox, intended to not break the rules but the bank. 

From “Meet the Man Who Hacked Jeopardy,” Jason Schreier’s Kotaku interview with a champion for the search-engine age:

“So what makes Chu so unusual? While most players will start from the top of each column on the Jeopardy board and progress sequentially as question difficulty increases, Chu picks questions at random, using what’s called the Forrest Bounce to hunt for the three Daily Doubles, which are often scattered among the harder questions in every game. Instead of moving from the $200 question to the $400 question and so forth, Chu might bounce between all of the $1,600 or $2,000 questions—not the kind of strategy you often see on Jeopardy.

Chu does this for two reasons. For one, it throws everyone off balance. ‘It’s a lot more mentally tiring to have to jump around the board like that,’ Chu told me.

More importantly, snagging those Daily Doubles offers him a massive statistical advantage. Since Daily Doubles allow players to bet up to their entire bankrolls, just one can swing an entire Jeopardy match—and Chu’s strategy is to control them all, even just to prevent other players from using them.

‘The only chance you have to give yourself an edge—the only moment of power, or choice you have in Jeopardy is choosing the next clue if you got the last one right,’ Chu said.”