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10 Biggest Jeopardy Winners, Ranked

The game show Jeopardy! is a cultural touchstone, having been on air since 1964. Over 8,000 episodes later, and it remains as popular as ever. Many people like to watch the trivia game and play along, but very few go to the lengths to audition for the show and potentially air their smarts on television.

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Take a look at the winnings of previous contestants, however, and many might be tempted to change their minds! Some of the brainiest people in America have managed to acquire some serious cash after participating in the competition. Here are the ten richest Jeopardy! contestants of all time.

10 Dan Pawson - $420,902

Dan Pawson, a legislative aide to Massachusetts state senator Bruce Tarr, had already made an impression on the show after accumulating $170,902 during a nine-day winning streak in 2008. What scored him a spot on this list, however, was winning the Jeopardy! Tournament of Champions a year later.

Every year, there is a tournament where previous champions are invited back to the show to go head-to-head. Fortunately for Dan, a former law student, many of the questions were law-related. He was able to win an additional $250,000. Add that to his previous winnings, and he's in the top ten richest Jeopardy! winners.

9 Ben Ingram - $426,534

IT consultant Ben Ingram can also thank the Tournament of Champions for helping him to get in the top ten. He garnered $176,534 in his initial run on the show in 2013, where he came out on top for eight games straight. After earning $250,000 at the 2014 Tournament of Champions, Ben was able to bring up his total Jeopardy winnings to $426,534.

The South Carolina native wasn't expected to beat out fellow contestants Arthur Chu and Julia Collins - both who had astounding track records on the show - but Ben came up from behind and took the lead.

8 Julia Collins - $478,100

Julia Collins had her first appearance on the show all the way back in 2014, but remains Jeopardy's richest female champion to this day. After winning 20 games in a row, Julia finally ended her streak by betting her entire total during the final round, and getting the answer wrong for once!

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Fortunately for Julia, she's been invited back to the show multiple times and continues to prove herself - as well as earn some more moolah! She participated in both the 2014 Tournament of Champions and the 2019 All-Star Games.

7 Jerome Vered - $499,102

Jerome Vered, a screenwriter from California, was certainly determined to get on the show. He took the test for Jeopardy! four times before finally securing a spot in the competition in 1992. His five-day winning streak was record-setting at the time, and he was later invited back to compete in the 1992 Tournament of Champions, 2005 Ultimate Tournament of Champions, and 2014 Battle of the Decades.

He has also gone on to compete in a bunch of other quiz games like Win Bein Stein's Money and the World Quizzing Championships.

6 Matt Jackson - $511,612

Matt Jackson was no stranger to the game's format, having won a bunch of trivia competitions with his Yale quiz bowl team. He was even president of the non-profit "Partnership for Academic Competition Excellence" for a time! After his friend won some money on the show,  the then-paralegal was encouraged to audition for himself.

He ended up having a thirteen-day winning streak in 2014, and then came in second place at the 2015 Tournament of Champions. Just this year, his team also won second place at the All-Star Games.

5 Roger Craig - $530,200

Roger Craig set the record for most money won in a single game, earning $77,000. His seven-day winning streak ended up giving him a total of $231,200. He was then invited back to participate in the 2011 Tournament of Champions, and ended up winning the whole thing. He also participated in the 2014 Battle of the Decades and the 2019 All-Star Games.

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The computer scientist was said to have used "data mining" techniques on all of the previous Jeopardy! questions ever given, helping him to correctly predict what categories were going to appear.

4 David Madden - $775,733.33

Those who knew art historian David Madden weren't particularly shocked that the man was able to draw out a 19-day winning streak in 2005. After all, he's the founder of the National and International History Bee and Bowl! Clearly, he knows his stuff.

After earning $432,400 in his initial run, David was invited back for the Tournament of Champions. Though he didn't win, he was given a consolation prize of $10,000, adding to his total. After winning $100,000,000 (split with two other team members) at the 2019 All-Star Games Tournament, his new grand total is $775,733.33.

3 James Holzhauer - $2,462,216

A professional sports gambler, James Holzhauer was prepared to dominate Jeopardy! He actually competed on other game shows The Chase and 500 Questions before finally appearing on Jeopardy! in 2019. James shocked viewers by winning 32 games in a row.

Needless to say, he was able to rack up quite a check during that streak! Dubbed "Jeopardy James" by the media, he is confirmed to be appearing in this year's Tournament of Champions to earn even more money. Meanwhile, James is using his current winnings to contribute to various charities and non-profits in the Las Vegas area.

2 Ken Jennings - $3,270,700

Ken Jennings became a TV star after appearing on Jeopardy! 75 times in a row in 2004. As one can imagine, winning 74 consecutive games has made him a multi-millionaire. He later got second place in the 2005 Ultimate Tourament of Champions, second place in the  2011 IBM Challenge, second place in the 2014 Battle of the Decades, and second place in the 2019 All-Star Games.

Ken has written several books, including Brainiac: Adventures in the Curious, Competitive, Compulsive World of Trivia Buffs, Ken Jennings's Trivia Almanac: 8,888 Questions in 365 Days and Maphead: Charting the Wide, Weird World of Geography Wonks.

1 Brad Rutter - $4,385,702

Brad Rutter has accumulated over four million dollars over a period of fourteen years. He initially had only a five-day winning streak in 2000, which doesn't seem as impressive as some of the other winning streaks on this list.

However, Brad was invited back for - and also won - the 2001 Tournament of Champions, the 2002 Million Dollar Masters Tournament, the 2005 Ultimate Tournament of Champions, the 2014 Battle of the Decades, and the 2019 All-Star Games. As of now, he remains the richest Jeopardy! contestant of all-time.

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