Rutter became a five-time champion on "Jeopardy!" in 2000. He later won four tournaments: the Tournament of Champions in 2001, the Million Dollar Masters tournament in 2002, the Jeopardy! Ultimate Tournament of Champions in 2005, and the Jeopardy! Battle of the Decades in 2014 His win in the Ultimate Tournament of Champions made him the highest winner on a game show. This was later beaten by Ken Jennings in 2007 when Jennings won $500,000 on "Are You Smarter Than a 5th Grader?". However, Rutter reclaimed the record after he won the Battle of the Decades tournament.