Complex sentence: Following his third tournament win, in which he defeated Ken Jennings and Jerome Vered in the finals and won the top prize of $2,000,000, Rutter surpassed Jennings as the highest money-winner ever on American game shows.
Split into simpler sentences: Following his third tournament win, in which he defeated Ken Jennings and Jerome Vered in the finals. Winning the top prize of $2,000,000, Rutter surpassed Jennings as the highest money-winner ever on American game shows.