Alex Trebek will host 'Jeopardy! The Greatest of All Time' with Ken Jennings, Brad Rutter, and James Holzhauer competing in a multi-night tournament. Which Jeopardy! contestant is the greatest of all time? We're about to find out. On Monday, ABC announced the return of Ken Jennings, Brad Rutter, and James Holzhauer — the highest money winners in the game show's history — to the Jeopardy! stage to compete in The Greatest of All Time, a multi-night tournament that will kick off Tuesday, Jan. 7 at 8 p.m. ET. Jennings holds the records for most consecutive games of Jeopardy! won and the highest winnings during regular-season gameplay (,520,700). Rutter maintains the top spot for highest winnings