The 10 Biggest Winners In Jeopardy History

When you add up the winnings in all the daily games and the various tournaments from the 10 biggest winners of Jeopardy! of all-time, it totals an astounding $19,874,486. Even more astounding is that about two-thirds of that total, $12,921,352, has been won by only three players, including the legend Ken Jennings and risk-taking phenom James Holzhauer. However, the player who has won the most in total winnings might not be the person you are expecting. 

An Important Rule Change 

For years, there was a rule on Jeopardy! that everyone who became a 5-Day Champion would “retire” from the game, take his or her winnings, and step down as a champ. They would automatically be invited to the annual Tournament of Champions, but beyond that, their run on one of the best game shows ever would be over. That rule changed before the start of Season 20 in 2003. As a result, the winnings by single players have increased dramatically, with nine of the current top ten winning their cash after the rule change. 

A Note About The Totals 

When looking at the top ten winners of all-time on Jeopardy!, including everything they won as a contestant on the standard game as well as in various tournaments over the years — like the Tournament of Champions and other one-off tournaments — there are some interesting numbers to unfold. The official Jeopardy! totals do not include consolation prizes, so those have been noted separately when applicable. Here are the winningest Jeopardy! contestants of all time. 

10. Victoria Groce ($622,801) 

Victoria Groce made her initial appearance on Jeopardy! back in 2005, when she won just a single game and earned $22,801. What was notable about the appearance, however, was that she was the player who ended the 19-game win streak of David Madden, who appears further down on this list. Because of that and her continued success in the world of trivia — she appears with other Jeopardy! alums on The Chase — Groce was invited to compete in the inaugural Jeopardy! Invitational Tournament in 2024, which she won to earn $100,000 and a ticket to Jeopardy! Masters. There, she defeated reigning champ James Holzhauer and 2024 Tournament of Champions winner Yogesh Raut to earn $500,000 and a spot on the Leaderboard of Legends. 

9. Larissa Kelly ($655,930)

In Season 25 in 2008, Larissa Kelly, a college professor originally from Newton, Massachusetts, won a six-day cash winnings total of $222,597. In 2009, she was the first runner-up in the Tournament of Champions, securing another $100,000, and she received one-third of the $1 million prize from the 2019 All-Star team tournament. With the $10,000 she got for making it to the JIT semifinals in 2024, the $5,000 she got as an invitee to 2014’s Battle of the Decades and her original $1,000 consolation, Larissa Kelly took home a total of $671,930.  

Her husband Jeff Hoppes also competed on Jeopardy! and was defeated by Ken Jennings on the 70th game of the champ’s historic win streak. In a funny coincidence, Hoppes went to high school with Jeopardy! great Brad Rutter. Kelly was the first female champion to win more than five games. Her six-win streak was the longest for a woman until Season 29. She also held the regular-play winnings record for a female champion until Season 30.  

8. Cris Pannullo ($748,286) 

 Cris Pannullo became the third player in 2022 to crack the Top 10 in all-time winnings, when he went on a 21-game win streak that started in September. During his run he accumulated $748,286 in winnings — good for eighth place on Jeopardy!’s Leaderboard of Legends — in addition to the $1,000 consolation prize for his final game and a $5,000 consolation prize from the 2024 TOC. His streak puts the customer success operations manager from Ocean City, New Jersey, at sixth place in consecutive wins, and only four contestants have won more money in regular-season play than Pannullo.  

7. David Madden ($763,733) 

David Madden, an art historian from Ridgewood, New Jersey, earned cash winnings totaling $430,400 in 2005. Following his 19-day run on the show, he also split the $1 million prize for being part of the 2019 All-Star team that included Larissa Kelly and Brad Rutter, for an additional $333,333. Not included in the official total are $10K from the 2024 JIT, the $10K consolation prize from his Tournament of Champions, and the $2,000 consolation from the loss in his 20th game. In total, Madden took home $785,733.   

6. Mattea Roach ($810,983)

Mattea Roach, who was 23 years old when they started their streak, is the youngest player on this list, with a run spanning April and May 2022. The tutor from Toronto compiled $560,983 in 23 victories. As well as becoming the winningest Canadian in the game show’s history — an honor that would make Alex Trebek proud — Roach also became one of just three contestants to reach their age in Jeopardy! victories. Roach came in second to James Holzhauer in the 2023 Jeopardy! Masters tournament to earn a cool $250,000, and when you add in the $75,000 parting gift from 2024’s Jeopardy! Masters,  $10,000 from the 2022 Tournament of Champions and their initial $2,000 consolation prize, they’ve taken home a total of $897,983.  

5. Matt Amodio ($1,668,601) 

Matt Amodio’s 2022 run on Jeopardy! ended just a couple of months shy of Amy Schneider’s first appearance, and while his 38-game win streak was two shy of hers, he came out with a higher amount of cash winnings in regular-season play, earning $1,518,601. Both Amodio and Schneider were supposed to appear on the game show before Alex Trebek’s death, but when COVID shut down production, each was given more time to study, which probably helped Amodio, as his time on the show came when Jeopardy! was auditioning guest hosts to find Trebek’s replacement. Amodio has competed under seven different hosts, and that’s likely a record that will never be broken. 

He also caused a bit of controversy with his answering strategy, responding with the contraction “What’s…” regardless of if the clue was in reference to a person, place, etc. He placed sixth in the 2024 Jeopardy! Masters tournament for $50,000, third in 2023’s Jeopardy! Masters to win $150,000, and in addition to the $10,000 for his appearance in the 2022 Tournament of Champions, and the $1,000 consolation prize from his regular-season loss, he has taken home $1,729,601 to date. 

4. Amy Schneider ($1,682,800)  

Second behind only Ken Jennings with 40 consecutive games won, Amy Schneider made history during her win streak in 2022. Early in her run, she became the first openly transgender champion to qualify for the Tournament of Champions, and she just kept winning! She crossed the million-dollar mark in regular-season play, earning $1,382,800, even before appearing in the Tournament of Champions. She went on to win that too, adding an extra $250,000 to her total, and in 2024 she earned another $50,000 as runner-up of the Jeopardy! Invitational Tournament. Though it doesn't count toward her official total, Schneider also received $100,000 for fourth place in 2024’s Jeopardy! Masters, $75,000 for her fifth-place finish on the 2023 Jeopardy! Masters, and with the $2,000 consolation prize from her regular season loss, Schneider has taken home a total of $1,859,800. 

3. James Holzhauer ($3,612,216)

A sports gambler from Las Vegas, Nevada, whose 32-day cash winnings totaled $2,462,216, Holzhauer took the Jeopardy! world by storm in the winter and spring of 2019, bringing in record ratings with his swashbuckling style and the odd, but daring, amounts of his bets on Daily Doubles and Final Jeopardy.

Holzhauer was not the first to use the style of bouncing around the board until the Daily Double was revealed, but he was especially good at keeping control of the board until he found it, when he would inevitably make his bet a “True Daily Double” and double his money when he virtually always answered correctly. The same thing happened in Final Jeopardy, when he would usually be so far out in front of his two competitors that he would be in a position to bet huge amounts and again, virtually always answer correctly.

James Holzhauer set the record for the highest single day total an astonishing 16 times over his 33-day run and finished with 21 of the 25 highest single-day scores, including winning $131,127 in one game on April 17, 2019. He went on to add $250,000 as the 2019 Tournament of Champions winner, another $250,000 as the runner-up in the 2020 Jeopardy!: The Greatest of All Time tournament, $500,000 in the 2023 Jeopardy! Masters tournament and $150,000 for third place in 2024’s Masters. Adding in the $2,000 consolation from his regular-season loss, he took home a total of $3,614,216. 

2. Ken Jennings ($4,370,700) 

The mighty Ken Jennings! A computer scientist from Seattle, Washington, compiled 74-day cash winnings totaling $2,520,700 plus another $500K for a second-place finish in the 2005 Tournament of Champions and $1 million and the title of “Greatest of All Time” in 2020’s GOAT Tournament. As the 2019 All-Star Games captain whose team was first runner-up, he won $100,000, got another $100K from the 2014 Battle of the Decades first runner-up and won $150,000 as first runner-up in the 2011 IBM Challenge. Adding the $2,000 consolation from the loss in his 75th-consecutive game puts him with a take-home total of $4,372,700.

Ken Jennings was the first true Jeopardy! celebrity contestant, expanding his popularity beyond just the show’s hardcore fans and into pop culture when he went on his almost unfathomable 75-day run in the summer of 2005. He was the first person to really take advantage of the rule change that allowed champions to keep competing until they were beaten, rather than being limited to five games.

Ken Jennings has parlayed his Jeopardy! celebrity into a career, writing trivia books, appearing on other game shows, and co-hosting a podcast called Omnibus with John Roderick. Following Alex Trebek’s death in November 2020, Jennings was the first guest host to take over, and he ultimately made that a permanent position. 

1. Brad Rutter ($4,938,436) 

So, at number one is someone you might not have expected: Brad Rutter, a record store employee from Lancaster, Pennsylvania, whose 5-day cash earnings in 2000 totaled $55,102. Yes, you read that right. Rutter was a 5-day Champion who had to retire after his first run. It’s been since then that Rutter has set records and proven he is easily one of the best players of all time.

In the years since being a 5-day champ, Brad Rutter has won $2 million in the 2005 Ultimate Tournament of Champions, $1 million in the 2002 Million Dollar Masters Tournament, another $1 million in 2014’s Battle of the Decades, and hundreds of thousands more in the 2001 Tournament of Champions, the IBM Challenge, 2019’s All-Star Tournament and the Greatest of All Time tournament in 2020. 

Honorable Mentions

Honorable mention goes out to Arthur Chu, a columnist from Broadview Heights, Ohio, whose controversial game play, annoying, aggressive buzzer pressing, and his penchant for getting snippy with host Alex Trebek made him a polarizing contestant among Jeopardy! fans in 2014. He won $298,200 over 12 games in 2014 and won another $100K for finishing second in that season’s Tournament of Champions. Chu returned to the Alex Trebek Stage in 2024 to compete in the JIT.

Another honorable mention goes out to Chuck Forrest, a contestant who, in the ‘80s, was once one of the best to play the game. Because of the 5-Day Champion rule, as well as the lower cash prizes when he played, Forrest doesn’t appear on the list, but his accomplishments are legendary, including being credited with a common strategy now known as the “Forrest Bounce,” when contestants bounce from clue to clue (a strategy that drove longtime host Alex Trebek nuts), rather than going one by one down a category as contestants were originally intended to do. Arthur Chu and James Holzhauer were both very successful using the “Forrest Bounce.” Forrest also made an appearance in the 2024 Jeopardy! Invitational Tournament.

Finally, a third honorable mention goes to IBM’s supercomputer known as “Watson,” whose artificial intelligence software was originally specifically designed to compete on Jeopardy! and faced off against Ken Jennings and Brad Rutter in a 3-day game in February of 2011. Watson won the game for a total of $77,000.

Winning a lot of money on Jeopardy! is hard work. These champions don’t just show up with their bad sweaters and inane personal stories and win without any preparation. Almost all these big-time winners studied the game intently before appearing on the show. They were members of esteemed trivia teams, watched thousands of hours of old games, read strategy guides, and even sought out the advice of past champions. They are also clearly pretty damn smart people. Ken Jennings’ record of 74-straight wins may never fall, but who knows?