Contestant Ken Jennings is the winner of ‘Jeopardy’s' entertaining tournament to name the mythical 'Greatest of All Time' player in the game show's history. Jennings won by being bold in Tuesday's tournament, three times betting all of his points on one question, and three times answering correctly. His closest competitor James Holzhauer had a chance to win when he bet all his points on a question about Shakespearean tragedies, but was wrong. Jennings won three matches, Holzhauer one and Brad Rutter came up empty.