The 5 ‘Jeopardy!’ Contestants Who Won the Most Money

While Jeopardy! welcomes many Trivial Pursuit masters to compete in a battle of stored knowledge, not many walk away with life-changing amounts of money. Getting to compete on the show is an honor, in and of itself, as many individuals apply for years to get a chance to appear on the show opposite Alex Trebek.

'Jeopardy' Alex Trebek
‘Jeopardy’ host Alex Trebek ” Frederick M. Brown/Getty Images

Some who apply never actually get a chance to meet Trebek. Yet, some competitors have gone on to take the game show by storm, claiming hundreds of thousands of dollars, if not more. So of the Jeopardy! contestants, who among them can claim the rights to the most money earned? Let’s go through the top five, according to reports from

5. Matt Jackson won over half a million dollars on ‘Jeopardy!’

Matt Jackson won 13 games of Jeopardy!, and claims the rights to one of the show’s longest winning streaks, earning a total of $411,612 throughout his original run. However, when he returned for the 2015 Tournament of Champions, he won another $100,000, bringing his total earnings to $511,612. Interestingly enough, to prepare for the show, Jackson used another winner’s book, Brainiac, written by Ken Jennings. 

RELATED: Who Hosted ‘Jeopardy!’ Before Alex Trebek?

4. Roger Craig won $530,200 on ‘Jeopardy!’

Roger Craig is a computer scientist who won over half a million dollars competing on the hit game show. He managed to beat Ken Jennings one-day winnings record when he appeared on the show, claiming $77,000 in 2015; Ken Jennings had previously won $75,000 in one day, as Insider notes. 

You can say Craig “out-smarted” the game itself; he reportedly used data-mining techniques, as well as text-clustering strategies to group questions — determining which were statistically common (and which were not). Talk about strategy, right? Maybe it’s not just about knowing a bunch of random facts about the world and all the people, galaxies, animals, and objects that comprise it. 

3. James Holzhauer broke $2 million! 

James Holzhauer won over $2 million by competing on the game show. He came to be a millionaire by winning 32 games in a row. He took some major risks, which led to some even greater payouts. In total, he won $2,426,216. Maybe his history as a professional gambler helped him here..though this may not be the strategy to success that a financial adviser would recommend. 

RELATED: Will ‘Jeopardy!’ Go On Without Alex Trebek?

2. Ken Jennings won $3,270,700 on the show

Ken Jennings is definitely one of Jeopardy!’s most famous contestants. If the amount of money he won isn’t memorable, his contagious personality sure is. Jennings holds the record for the game’s longest winning streak, as he won 74 games in a row!

RELATED: What is ‘Jeopardy!’ Champ Ken Jennings’ Net Worth Today?

1. Brad Rutter won $4,385,702

While Ken Jennings is arguably the most famous contestant to ever compete on Jeopardy!, he did not win the most money on the show. The honor belongs to Brad Rutter, who has made over $4 million on the show across a 14-year span. He raked in the big bucks by winning The Tournament of Champions, The Ultimate Tournament of Champions, and the Master Tournament of Champions, as well as The Battle of the Decades.