James Holzhauer is trying to prove he is the greatest Jeopardy! player of all-time. The Naperville native is facing off against Ken Jennings and Brad Rutter in the “Jeopardy! The Greatest of All Time” tournament. All three are the biggest winners in the quiz show’s history. Holzhauer lost by just 200 points to Jennings in the first matchup last night, with Rutter coming in third. The first person to win three matches receives one-million-dollars.