James Holzhauer will battle Ken Jennings and Brad Rutter in the Alex Trebek-hosted Jeopardy!: Greatest of All Time tournament that kicks off on Jan. 7 at 8 p.m. “When James had his run last year, a lot of people were wondering, well how would he do against Ken Jennings? How would he do against Brad Rutter? (They’re) our two most successful players in Jeopardy! history,” Trebek tells USA Today. “These three players have won close to $10 million in Jeopardy! prize money and over 100 games among them, so it was logical.” According to USA Today, the tournament won't be typical: "It consists of a series of two back-to-back games, airing weeknights (8 EST/PST) beginning Jan. 7. The player with the most combined winnings from the two games wins the 'match,' and the play continues on successive nights (except Monday) until one of them has won three matches and takes home a $1 million prize. (The other finishers get $250,000 apiece). That means the tournament can last anywhere from three to seven days." ABC reality chief Robert Mills calls the tourney his "dream project." "I don't know how this doesn't become an event," he says. Watch the Jeopardy!: Greatest of All Time teaser.