5 Facts About Brad Rutter, the Highest Winning 'Jeopardy' Contestant

On Tuesday, the three biggest money winners in Jeopardy! history will compete in the "Greatest of All Time" contest, including highest earning contestant Brad Rutter.

Rutter's first appearance on Jeopardy was on October 3, 2000. He won five days in a row, before retiring with $55,102 in winnings. Jeopardy! rules changed in 2003, allowing contestants to play more than five days in a row. Since his initial run, Rutter has returned for the Tournament of Champions, Million Dollar Masters, Ultimate Tournament of Champions, All Star Games and the Battle of the Decades. His total official Jeopardy! winnings are $4,688,436.

Much has been written about Rutter and his Jeopardy! experience, but here are five lesser-known facts about the contestant:

Never Lost to a Human Opponent

Unlike his opponents Ken Jennings, who won 74 straight games, and James Holzhauer, who won 32 straight games, Rutter has never lost an official game, except when he and Jennings faced off against IBM's Watson, question-answering—or is it answer-questioning?—computer system.

Rutter and Jennings faced off in an exhibition match against Watson in February 2011. At the end of the three-day match, Rutter finished in third place, with $21,600, behind Watson's $77,147 and Jennings' $24,000.

Friends With Ken Jennings

In an interview with TMZ, Rutter said that despite the two competing for the top spot, he's friendly with Jennings. "In fact, we're kinda the only two guys to know what it's like, up to this point," he said.

He also said their mutual loss to Watson helped forge their friendship. "That Watson thing—both getting spanked like that—was kind of a bonding experience too," he told TMZ.

In a 2005 faceoff against Rutter in the Ultimate Tournament of Champions, Jennings wrote "Go Brad!" in his Final Jeopardy! answer.

Self-Described Slacker

In a 2005 interview with The Baltimore Sun, Rutter described himself as "not ambitious" despite being a pretty good student and avid reader. "My attention span was not great," he told the Sun. "I was a slacker, and I could coast." He studied English at Johns Hopkins University, but dropped out.

Created His Own Game Show

According to the Pittsburgh Post-Gazette, Rutter used some of his Jeopardy! winnings to produce and host his own quiz show InQuizitive, which aired in central Pennsylvania and tested high schoolers on their knowledge. Rutter told Trivia Hall of Fame that writing questions for the show helped him for future Jeopardy! appearances. "It keeps you sharp. Even when you're researching things that you won't use on the show, you're learning things and they stick with you," he told Trivia Hall of Fame.

More Appearances Have Made Him a Stronger Jeopardy Player

In a 2014 Reddit AMA, when asked if his continued appearances made him a better player, he agreed. "It's become easier for me over the years, just because I've sort of got used to it," he wrote. "No one who hasn't been on the show realizes what a bizarre experience it is. The more comfortable you can be in that milieu, the better you'll do."