Why Ken Jennings Hasn’t Won The Most Money In ‘Jeopardy!’ History Despite Winning The Most Games By Far

Ken Jennings stands alone in the pantheon of super champions. His 74-game steak remains a record far out of reach, yet he is not the all-time earner in the show’s history. Brad Rutter sits comfortably above Jennings in terms of all-time winnings despite competing during the five-episode era. How is that possible?

Brad Rutter: Ahead Of His Time

In 2003, Jeopardy! changed its rules to allow contestants more than five games on the show. Up until then, no one could spend more than one week competing. The change occurred just in time for Jennings, who went off on his 74-game streak beginning in 2004.

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When Rutter appeared on Jeopardy! in 2000, he was limited to only five days on the show. He managed to win $55,102 in that stretch, and two brand new Chevy Camaros. The steak earned him guaranteed entry into the 2001 Tournament of Champions. Rutter won that tournament, earning another $100,000 in the process.

The King Of ‘Jeopardy!’ Tournaments

The 2001 tournament was the first of many, many tournaments win for Brad Rutter. In 2002, he was invited back for the Million Dollar Masters Tournament, which he won. In 2005, he went toe-to-toe with Ken Jennings for the first time in the Ultimate Tournament of Champions. Rutter won that game, making him the highest money-winner in the history of American game shows at the time.

Fast forward to 2014 and Rutter and Jennings appeared in the Battle of the Decades tournament. With $1 million up for grabs, Rutter beat Jennings in Final Jeopardy yet again. You should notice a pattern here: Rutter beat Jennings again and again to boost his career earnings. He split a $1 million jackpot in 2019’s Jeopardy! All-Star Games. That’s five major tournament wins to throttle his career winnings well past Jennings.

The Greatest Of All Time

Then in 2020, Ken Jennings and Brad Rutter competed for perhaps the final time in the historic Jeopardy! The Greatest of All Time tournament. The two squared off against James Holzhauer, each with a valid claim to being the greatest in Jeopardy! history. As Alex Trebek pointed out on the broadcast itself, the tournament really changed very little about all-time rankings. Jennings won, but his $1 million prize was not enough to unseat Rutter.

The Greatest of All Time tournament leaves Jennings with $4,370,700 in all-time winnings. Rutter is still on top with $4,938,436. Since Jennings is now hosting Jeopardy!, he may never get a chance to make up that $567,736. One can’t help but wonder how Rutter would have fared if he went on Jeopardy! just a few days later. With his obvious skill, he could have gone on a streak to rival Jennings himself. As it stands, he can rest happily with his millions.

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