10 People Who Made the Most Money on Jeopardy!

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Brad Rutter: $4,688,436

Brad Rutter remains the all-time biggest winner of Jeopardy! according to the game show’s Hall of Fame. His total winnings, including tournaments, of more than $4.5 million, were accumulated over 14 years beginning in 2000 when he was just 22 years old. At that time, contestants could win a maximum of five consecutive games. Rutter has never lost a Jeopardy match to a human. After congratulating James Holzhauer on his epic run he tweeted, “I’m a little bummed to no longer be the “@Jeopardy champion personally recognized by the most Las Vegas casino employees.”

Ken Jennings: $3,370,700

Ken Jennings is the second largest all-time winner earning $3,370,700. He also holds the record for winning the most consecutive games (74) and the highest winnings during regular season play ($2,520,700). Jennings notes that a recent rule change that allowed contestants to remain on the show indefinitely permitted him to dominate air time for six months. He ultimately lost the show on a question about H&R Block.

James Holzhauer: $2,464,216

The professional sports gambler from Las Vegas created a new level of buzz for Jeopardy! keeping viewers glued to the screen during his 32-week run. He trails Jennings by just $58,484 for highest winnings in a regular season, a feat he accomplished in 32 games compared to Jennings’ 74 game run. He also holds all 10 spots for single-game winnings consistently breaking his own records with his top high win of $131,127. His signature strategy of betting on top dollar amounts first, waging amounts related to important personal dates, and betting big on the Daily Double served him well.

Dave Madden: $773,733

Dave Madden’s total winnings of $773,733 puts him in fourth place of all-time Jeopardy! winnings. He is third in regular season winnings at $430,400 winning 19 games in 2005. After his stint on the show, the art historian hiked the length of the United States for the Fisher House Foundation. The founder and Executive Director of the National History Bee and Bowl, Madden, like Holzhauer, hunted for the Daily Double.

Larissa Kelly: $660,930

Along with being the top woman money winner ($660,930) on Jeopardy!, Princeton graduate Kelly was the first woman to win five consecutive games in a row. Kelly’s husband and sister also were on contestants on Jeopardy! Kelly and fellow Princeton grad Dave Madden appeared in Jeopardy! All-Star Games. These are the Jeopardy! categories that trip the most people up.

Matt Jackson: $611,612

Back in 2015, Matt Jackson won 13 consecutive games, putting him in fifth place for consecutive games won as well as number five for highest winnings in a regular season of $411,612. The Yale graduate was just 23 years old when he played in 2015 and was best known for his rapid responses and quirky expressions like yelling “Boom!”

Roger Craig: $530,200

Back in 2010, Roger Craig trumped then single-day winner Ken Jennings by winning $77,000 in his six-day winning streak. Fast forward to 2019, when phenom James Holzhauer dethroned Craig by winning $110,914. Craig currently is number ten for highest single day win in a regular season of $230,200. Meanwhile, Holzhauer broke his own record three more times. (Try these memory-boosting tricks from a Jeopardy! contestant.)

Colby Burnett: $480,334

Colby Burnett, a Jeopardy! winner of $480,334, has the double distinction of 2012 Teachers Tournament and 2013 Tournament of Champions winner. The Chicago native and college counselor at Speer Academy is involved in the national trivia community. At the time of his victories, he was an AP History teacher at his Alma Mater Fenwick High School and said he would help his mother buy a house if he won $100,000.

Julia Collins: $478,100

CEO and Founder of Girls Like Me Julia Collins is a leading lady in two categories: She won 20 consecutive games in 2014 and has the highest winnings for a female in regular season raking in $428,100. The champion is ranked number three in consecutive games, number four in regular-season play and number nine in all-time winnings (including tournaments) for her total winnings of $478,100. She lost on a question about Oscar-winning writers whose correct answer was New England writer John Irving.

Austin Rogers: $461,000

Animated contestant Austin Rogers was best known for his pantomimes and energy. Tenth in all-time winnings (including tournaments) for his total of $461,000, he also is number six in the consecutive game wins for his 12-game streak in 2017 and also is in sixth place for highest winnings (regular season play) at $411,000.

Next, find out why Alex Trebek has never wanted to retire.