The 10 Biggest Winners In Jeopardy History

It's pretty amazing to think back to all of the big names Jeopardy! has produced in the past four decades, and it's even more exciting to know the list of Jeopardy!'s biggest winners is always changing. You never know — the next Ken Jennings or James Holzhauer could show up any day on the 2025 TV schedule.

Each of the top 6 on Jeopardy!'s Leaderboard of Legends has earned six figures on arguably the best game show ever, so let's take a look at the Top 10. First, a couple of notes about this list:

An Important Rule Change 

For years, there was a rule on Jeopardy! that contestants could win a maximum of five consecutive games before stepping down with an invitation to return for the annual Tournament of Champions. That rule changed before the start of Season 20 in 2003, allowing every player to proceed until they lost, and as a result, the win streaks and money earned by single players increased dramatically. In fact, only one of the 10 winningest Jeopardy! champions on this list competed on the show prior to the rule change.

A Note About The Totals 

The winnings attributed to the top 10 winners of all time on Jeopardy! include 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 Jeopardy! Masters. However, the official Jeopardy! totals do not include consolation prizes (which are sometimes significant amounts of money), so those have been noted separately on this list when applicable. Here are the winningest Jeopardy! contestants of all time:

10. Cris Pannullo ($748,286) 

Cris Pannullo was one of three players in 2022 to crack the Top 10 in all-time winnings, going on a 21-game win streak. During his run he accumulated $748,286 in official winnings, as well as 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.

9. 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.

8. Victoria Groce ($772,801)

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. 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 TOC winner Yogesh Raut to earn $500,000, and she added $150,000 more by placing third in the 2025 Masters tournament.

7. Mattea Roach ($810,983)

Mattea Roach, who was 23 years old when they started their streak in 2022, is the youngest player on this list. 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.

6. Yogesh Raut ($1,096,403)

In 2023, Yogesh Raut won $96,403 in three Jeopardy! victories, becoming just the second contestant to advance to the TOC with so few wins. He made the most of it, too, winning the 2024 Tournament of Champions to collect $250,000 and advance to Jeopardy! Masters Season 2, where his second-place finish earned him another $250,000. He returned to Masters in 2025 and defeated Victoria Groce and Juveria Zaheer for the $500,000 grand prize, making him the sixth millionaire in Jeopardy! history. He also earned a $2,000 consolation prize from his initial run.

5. 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.

4. Matt Amodio ($1,818,601)

Matt Amodio’s 38-game win streak in 2022 ended just a couple of months before Amy Schneider’s first appearance. He won $1,518,601, and almost as impressive as that is the fact that Amodio has competed under seven different hosts, as his time on the show came when Jeopardy! was auditioning guest hosts following Alex Trebek’s death.

In 2025 he won the JIT to earn $150,000, which followed his sixth-place finish on 2024 Jeopardy! Masters for $50,000 and third in 2023’s Jeopardy! Masters to win $150,000. Not counting toward his official winnings are the $75,000 consolation prize from 2025's Masters, $10,000 for his 2022 TOC appearance, and the $1,000 consolation prize from his regular-season loss. Altogether he's taken home $1,954,601 to date.

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 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 bounce around the board in search of the Daily Double, but he was especially good at keeping control until he found it. His gesture of going "all in" to make it a True Daily Double has been picked up and copied by numerous contestants since, but his ability to double huge amounts of money stands unrivaled. He finished his 33-day run with 21 of the 25 highest single-day scores, including the biggest one-day total ever: $131,127 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 (plus 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 as the 2014 Battle of the Decades first runner-up and won $150,000 as first runner-up in the 2011 IBM Challenge. Small potatoes now, but he also took home $2,000 as a consolation from the loss in his 75th-consecutive game.

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 74-day win streak in the summer of 2005. He parlayed his Jeopardy! celebrity into a career, writing trivia books, appearing on other game shows, and co-hosting the podcast Omnibus.

The GOAT would also serve as the first guest host to take over following Alex Trebek’s death in November 2020, a position he ultimately made permanent. Now, as the host, Ken Jennings is technically banned from ever returening as a player, but EP Michael Davies has suggested he'd be willing to make an exception if Jennings ever got the itch.

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. His winnings have primarly come in tournaments, proving his place 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.

After a five-year hiatus, he returned to the Alex Trebek Stage (thanks to James Holzhauer) for Jeopardy! Masters Season 3, where he placed 7th out of 9 and earned $15,000 (not counted toward his official total).

Honorable Mentions

Julia Collins won nearly $500,000 from her appearances in the 2014 season and 2019 All-Star Games, and while that may no longer be enough for the top 10, she remains at No. 7 in Most Consecutive Games Won. Her win streak lasted for 20 games, and those who followed haven’t forgotten how she paved the way, with both Amy Schneider and Mattea Roach mentioning her when they reached their own respective 20th victories.

Another honorable mention goes out to Chuck Forrest, because if you have a popular play style named after you, you deserve to be on this list. Forrest competed in Season 2 in 1985, where he won the maximum five games and ultimately the 1986 TOC. In an era where contestants typically chose clues in order from top to bottom of a category, he preferred to jump around the board to throw other players off. The strategy became known as the “Forrest Bounce,” and despite the fact that it drove Alex Trebek nuts, it’s the preferred style of play in Jeopardy!’s current era. Forrest was invited back to participate in the 2024 Jeopardy! Invitational Tournament, where he lost in the quarterfinals.

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

Brad Rutter and Ken Jennings may not have beat Watson but will anyone ever be able to top Rutter’s nearly $5 million in winnings? Will a contestant ever last long enough to surpass Jennings’ 74-game winning streak? Those benchmarks seem pretty insurmountable, but only time will tell.