There are a few levels of Jeopardy! smart.
- The folks who can shout correct answers most of the time when they are watching the show on their television sets.
- The folks who get on the show, after rigorous testing and auditioning to test those smarts.
- The folks who not only win on Jeopardy!, but go on to win and win and win beyond what is imaginable, to the point where it seems impossible that anyone could defeat them.
For example, there’s Ken Jennings, probably the most famous super champion of Jeopardy!, the record-holder for most money won in regular games, and the player to have won the most consecutive matches in non-tournament play.
Or James Holzhauer, who won “only” 32 games, but broke the long-standing one-day total by leaps and bounds, and nearly broke Ken Jennings regular season record for most winnings.
(Both also holding the top Coryat scores in Jeopardy!… but more on that here.)
Or Brad Rutter, who, despite limitations in his initial run, went on to be the record-breaking money winner in the show’s history.
Perhaps not coincidentally, all of these extraordinarily brainy gentlemen have gone on to form the team of brainy permanent panellists on the TV game show The Chase (as well as a few other game shows). Let’s have a look at how they won—and lost—on Jeopardy!.
Who Defeated Brad Rutter?
- The producers of Jeopardy!
- A computer
- Ken Jennings
Who is Brad Rutter?
Brad Rutter is a Pennsylvania native, National Academic Championship Hall of Famer, former record store clerk, radio host, and an absolute superstar in the world of Jeopardy!
How is He a Jeopardy! Giant?
Rutter was undefeated by humans for nearly twenty years (more on that in a bit) and he has won the most money on Jeopardy! of any contestant in the show’s history, a staggering $4,938,436. (For more info on how much money that actually looks like for the winner, check out this article.)
His gameplay can be described as, well, excellently thorough; his tactics are not exotic, he just knows a lot, studies rigorously, and is a huge fan of the game.
How Was He Defeated?
Reaching Limits
When I say he was defeated by the show’s producers, that’s a bit of a fib; in the olden times of October 2000, when Rutter first appeared, there was a cap on how many games a contestant was able to play/win. So, once he won five games (and $55,102), his reign was over.
But that, obviously, wasn’t really the end.
Undefeated for More Than a Decade
As a five-time winner, Rutter was invited to compete in the Jeopardy! Tournament of Champions in 2001, which he won, along with $100,000.
In 2002, he was invited back to the Million Dollar Masters Tournament, which he also won.
In 2005, he came back again, this time for the Ultimate Tournament of Champions; unshockingly, he also won that, defeating Ken Jennings in direct competition for the first time, too. The prize was $2,115,000.
Skynet IBM’s Watson
Rutter was invited back to the Jeopardy! stage, and to compete with Jennings again, in 2011 for a special event called The IBM Challenge, a three-day affair with two days of competition against a specially programmed computer called Watson. This Man vs. Machine battle was riveting, weird, and more than a bit science fiction-y, because, in the end, Watson defeated the humans. And for even more weird and wild Jeopardy! scores and moments, check out this article.
Another Undefeated Near-Decade
Rutter came back for the Battle of the Decades in 2014, winning the tournament, and another million dollars, then formed an All-Star team with fellow super-champs Larissa Kelly and Dave Madden for a special two-week event in 2019, again winning the whole thing.
You might think getting beaten by a computer that knew, oh, everything (though still had some glitches) might be the end of the line for a game show contestant, but, this is Jeopardy!, and, boy, do those showrunners love a new tournament idea. Or two.
Ken Jennings competed in both of these, too, by the way, ending up in the first runner-up position each time.
The GOAT?
In January 2020, the three top players (Rutter, Jennings, and James Holzhauer) were invited back to compete in a two-day Greatest of All Time tournament. Rutter, for the first time ever, faltered, coming in third on both days of the competition. What happened?
Rutter himself said that he just wasn’t prepared enough, especially on buzzer timing; Jennings and Holzhauer just had the knack, and Rutter couldn’t get in. Finally! Something about a super champion’s Jeopardy! Experience that I can relate to! (James is a danged machine with the signaling device; I…was not.)
Who Defeated Ken Jennings?
- Nancy Zerg
- Brad Rutter
- Watson
- Brad Rutter
Who is Ken Jennings?
Wow. WOW. You’re reading an article about Jeopardy! and you need me to explain who Ken Jennings is? Wow.
Ken Jennings is a phenomenal player from Washington State, who, before he dominated the trivia world, was a software engineer for a healthcare company. His Jeopardy! notoriety has led to a totally different career, though, as a genuine celebrity and trivia guru, writing books, columns, and games for our edification. (Sign up for his email list if you want some genuinely tricky, curated trivia questions in your inbox.)
Oh, and his association with Jeopardy! is so strong that he was also the first guest host of the show after the passing of beloved host Alex Trebek (and some say that he is a frontrunner to take over the gig permanently).
How is He a Jeopardy! Giant?
How isn’t he?
As mentioned above, in 2003, the show eliminated the five-game limit rule for Jeopardy! champions. Jennings started his run on the show not after, and was a five-game champion nearly 15 times over, winning a total of 74 regular games, and $2,520,700 in those games.
Additionally, he has won a whole load of tournament money (though, not quite as much as Brad Rutter, whom he has only beaten once), for a total of $4,370,700.
How Was He Defeated?
In his 75th game, Jennings had, well, a not-great day, missing two Daily Doubles, and going into Final Jeopardy! without the commanding lead that had become his signature; he had $14,400 compared to second-place, and super solid player, Nancy Zerg’s $10,000. Without a cushion of cash to enable a shut-out, Jennings needed to get the Final Jeopardy! clue correct AND needed to bet big.
In this case, well, it didn’t work out.
But don’t feel too sorry for him; H&R Block offered to do Jennings’ taxes for free for the rest of his life. And he had plenty of victories ahead.
The GOAT!
As mentioned above, in addition to losing to IBM’s Watson, Ken Jennings had a bit of a Brad Rutter problem, coming in second to him in the Ultimate Tournament of Champions in 2005, the Battle of the Decades (2014), and the multi-week team games in the All-Star Tournament (2019). (Jennings DID however come in second place to Watson, and Rutter came in third.)
(Note: not an actual image of Watson.)
It took until 2020 for Jennings to conquer his foe (and friend), when he was (finally!) crowned The Greatest of All Time.
Who Defeated James Holzhauer?
- Emma Boettcher
- Ken Jennings
Who is James Holzhauer?
James Holzhauer is a more recent addition to the list of legendary Jeopardy! players, and, phew, he is a phenom.
He’s a math whiz and professional gambler based in Las Vegas (of course) who made a mission out of getting on Jeopardy! (in part to honor his grandmother), then used his betting moxie and know-how to maximize his winnings, like, a lot.
How is He a Jeopardy! Giant?
Although he “only” won 32 regular games, he won $2,464,216, nearly matching Jennings’ total ($2,520,700) in far fewer matches (remember, Jennings’ won 74). He also holds the top 16 one-day totals in regular Jeopardy! games.
A big part of the “how” of his incredible $70K+ per-game average is that, in addition to his mega-buzzer prowess, and his incredible breadth of knowledge, he bet big, and was able to bet big by going for the highest-value clues right away in each of the Jeopardy! and Double Jeopardy! rounds, instead of a more classic “start at the top of the category, where the easiest clues lie” strategy. He didn’t invent this strategy, but he definitely made it his signature.
Why would he do this? Two reasons:
- To accumulate as much money as possible quickly.
- To have more to bet with on finding a Daily Double. (Better to have a few thousand than a few hundred to wager, right?)
He bet a lot, and his years of experience as a professional gambler gave him a real understanding of how to bet optimally. Knowing how to wager in Jeopardy! is the third key to being a phenomenal player and champion, and it’s probably the most neglected one. (When I was preparing to compete on the show, my eyes glazed over any time I tried to read what the experts had to say, but I hadn’t taken a stats class in 20 years—one in which I got a C.)
How Was He Defeated?
One person who did not neglect Jeopardy! math in training for the game was Emma Boettcher, a librarian who, as well as also having a truly excellent knowledge base, had studied game theory at graduate school.
And not just any game: She wrote her Masters’ thesis ABOUT Jeopardy!
She also sought higher-value clues, to such a degree that, in her (first) showdown with Holzhauer, Alex Trebek suggested that she might have picked up tricks from him.
Nope. The first time she saw him play was when she played him; none of his episodes had aired by the time she got on the Jeopardy! stage, and her giant-killing victory over Holzhauer was a Monday game, meaning that it was the first one (of five) taped on the day of recording.
It was an epic game, and Boettcher found two Daily Doubles (betting well, answering correctly, which is, of course, key!),so, going into Final Jeopardy, Holzhauer was in the rare position of not being a runaway victor (a scenario he only faced three times over his previous 32 games). All three competitors got the correct answer (Kit Marlowe), but Holzhauer relatively modest bet (some corners of the Internet questioned the strategy, thinking he “threw the game,” but here’s the rationale behind it), and Boettcher’s aggressive double-or-nothing one, led to this ending.
And, thus, Emma Boettcher became a Jeopardy! legend.
Holzhauer seems to have taken it in stride that he was defeated, but not without a tinge of his ultra-confident mien: “I lost to a really top-level competitor,” Holzhauer said. “She played a perfect game. And that was what it took to beat me.”
Rematch
Holzhauer did get his win back from Emma, eventually, though.
Even though Boettcher’s run of winning matches only lasted three days (still impressive!), she earned a wild-card spot into the November 2019 Tournament of Champions; both made the two-day final, and, this time, Holzhauer won. (Though, at times, Boettcher looked poised to take him down once again.)
Not the GOAT?
As mentioned above, Holzhauer did have one more defeat, though, because, of course, the battle for the title of Greatest of All Time in January 2020 resulted in a victory for Ken Jennings, but, given Jeopardy!’s penchant for creating new and exciting ways to bring back champions (and fan favorites), he’ll probably get another chance to finally conquer his Chase costar.
So, how do you beat a Jeopardy! giant? You have to be exceptional in every aspect of the game (1. Extensive knowledge of Jeopardian subjects, 2. Buzzer acumen, 3. Betting strategy), and also pretty darned lucky—maybe the giant will get tired and start making spacey mistakes, or “your” categories will just come up again and again.
At any rate, it ain’t easy, so get practicing! Dive into Trivia Bliss quizzes, find out more about how Jeopardy! preps its competitors, how hard it really is to get on an episode, how you can prepare to be on Jeopardy! yourself, its taping schedule, and, of course, keep watching Jeopardy!
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