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Ken Jennings, IBM's Watson, and Brad Rutter

If you added up all the winnings in all the daily games and the various Tournaments the biggest winners of Jeopardy! have won of all-time, it totals to an astounding $14,517,261. Even more astounding is that two-thirds of that total, $10,521,352, has been won by only three players, including the legend Ken Jennings and the most recent phenom James Holzhauer, but the player who has won the most in total might not be the person you are expecting.

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 be automatically be invited to the annual Tournament of Champions, but beyond that, their run would be over. That rule changed before the start of Season 20 in 2003. As a result, the winnings by single players has increased dramatically, with nine of the current top ten winning their cash after the rule change.

When looking at the top ten winners of all-time on Jeopardy!, including everything they won as a daily constant on the standard game as well as any money that has been won in various tournaments over the years -- like the Tournament Of Champions and other one-off tournaments the show has conducted -- there are some interesting numbers to unfold. Here are the winningest.

Wacky Austin Rogers on Jeopardy!

10. Austin Rogers ($461,000)

One of the “wackiest” contestants in Jeopardy history was Austin Rogers, a bartender from New York City, whose 12-day cash winnings totaled $461,000. Rogers was as known for his goofy looks and pantomimes when he was introduced as he was for his skills as a Jeopardy! player. Before the recent run by James Holzhauer, Rogers held the record for the third-highest single-day total with $69,000.

Julie Collins on Jeopardy!

9. Julia Collins ($478,100)

Julie Collins, a supply chain manager from Kenilworth, Illinois, whose 20-day cash winnings totaled $478,100 has the 4th longest daily streak in Jeopardy history and the longest by a woman. When her streaked ended on June 2nd, 2014, she ranked third all-time in winnings. There is no question that her MIT education was an asset in her record streak.

Colby Burnett on Jeopardy!

8. Colby Burnett ($480,334)

Colby Burnett, a schoolteacher from Oak Park, Illinois who ZERO-day cash winnings total $480,334 is unique because all of his winnings have coming tournaments, first by winning the annual Teacher’s Tournament in 2012 and then by winning $250K a few months later, in February of 2013, in the Jeopardy! Tournament Of Champions.

Roger Craig on Jeopardy!

7. Roger Craig ($530,200)

Roger Craig, a computer scientist from Ferndale, Pennsylvania whose 7-day cash winnings totaled $231,200, plus another $250K for winning for Tournament of Champions as well, plus more earned in various other tournaments and special games, like the 2019 All-Star Games. In Craig’s second game, first as a returning champion, he set the record at the time for the largest single-day take on Jeopardy!, winning $77,000 in one game, including $30K in Final Jeopardy.

Matt Jackson on Jeopardy!

6. Matt Jackson ($611,612)

A college student whose 14-day cash winnings totaled $413,612, plus a second place finish in his season’s Tournament Of Champions and another $35K in other special games, Matt Jackson finished his 13-show run in 2015 as the fourth-highest earner in Jeopardy! history. The graduate of Yale had tried twice to compete in the College Tournament, but was unsuccessful both times. Instead, he was finally successful in getting on the regular show and he certainly took advantage of it.

Larissa Kelly on Jeopardy!

5. Larissa Kelly ($660,930)

Larissa Kelly, a college professor originally from Newton, Massachusetts whose 7-day cash winnings totaled $222,597 plus splitting a $1,000,000 prize by winning an All-Star team tournament. Her husband Jeff Hoppes is also famous in Jeopardy! circles for being the man who finally defeated Ken Jennings after his legendary 74-day run as champion.

David Madden on Jeopardy!

4. David Madden ($773,733)

David Madden, an art historian from Ridgewood, New Jersey whose 20-day cash winnings totaled $432,400. Combined with splitting the winning $1,000,000 prize for being part of the All-Star team that also included Larissa Kelly and another $10K as a consolation prize in his Tournament Of Champions (which he did not win), Madden was, at the time, the third most successful Jeopardy! contestant of all-time.

James Holzhauer Screenshot from Jeopardy! 2019

3. James Holzhauer ($2,462,216)

A sports gambler from Las Vegas, Nevada whose 33-day cash winnings total $2,464,216, 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 early on in his run, on April 17th, 2019. If you take just his top six finishes, he would STILL rank #3 on this lists, with $809,656!

It’s also important to note this total includes NO tournament winnings like virtually ever other player on this list, at least at the time of this writing. His daily game total ranks second behind Ken Jennings, but he came within $100K in just half the games! It was an amazing run that shocked people when it ended.

Jeopardy! superstar Ken Jennings

2. Ken Jennings ($3,370,700)

The mighty Ken Jennings! A computer scientist from Seattle, Washington whose 77-day cash winnings totaled $2,522,700 plus another $500K for a second-place finish in his season’s Tournament Of Champions, the rest of the $3.37 million total came in various special games he’s participated in over the years, Ken Jennings is one of the most well-known Jeopardy players.

Ken Jennings was the first true Jeopardy! celebrity contestant, expanding his popularity beyond from 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 recent rule change, allowing champions to keep competing until they were beaten and no longer bound to the 5-Day retirement rule for champions.

During his run, he set the record for most days as champion, 74, which still holds today, the highest total cash earnings, $2.5 million, and what was at the time, a single-day record of $75,000, which has since been broken by Roger Craig and James Holthauer (a bunch of times).

Ken Jennings has parlayed his Jeopardy! celebrity into a career, writing trivia books, appearing on other game shows, including a number of special appearances on Jeopardy! and currently co-hosts a podcast called Omnibus with John Roderick.

Brad Rutter on Jeopardy

1. Brad Rutter ($4,688,436)

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 total $55,102. Yes, you read that right. Rutter was a 5-day Champion who had to retire during his first run back in 2000. It’s been since then that Rutter has set records and proven he is easily one of the best players of all time. In 19 games, he has never lost to a human opponent in Jeopardy, but he did lose to Watson (see below).

In the years since being a 5-day champ, Brad Rutter has won an amazing four tournaments. The 2001 Tournament Of Champions, the 2002 Million Dollar Masters Tournament, the 2005 Ultimate Tournament Of Champions and the Battle Of The Champions in 2014. His team also split the $1,000,000 All-Star tournament earlier this year.

It’s is an absolutely incredible record that Rutter has on the show. Among serious Jeopardy fans and contestants, he has been the most fear competitor for years. It’s going to really cool to see how James Holzhauer stacks up against Brad Rutter (and Jennings for that matter) when the show inevitably comes up with a format for the three to face off.

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. He won $298,200 over 12 games in 2014 and won another $100K for finishing second in that season’s Tournament Of Champions.

Another honorable mention goes out to Chuck Forrest, a contestant who in the ‘80s was once one of the best to play the game. Forrest is sort of the Babe Ruth of Jeopardy!. Because of things like the 5-Day Champion rule, as well as the lower cash prizes when he played, he doesn’t appear on the list, but his accomplishments are legendary, including with being credited with a common strategy now known as the “Forrest Bounce” when contestants bounce from clue to clue, not 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.”

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 and won 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 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 75-straight days as champion may never fall, but who knows?

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