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How One Contrarian ‘Broke’ Jeopardy! and Won $1.7 Million

For all practical purposes, the way Jeopardy! is played hasn’t changed much since Art Fleming provided the game show’s first “answer” 55 years ago. At least, that was the case until James Holzhauer took his place behind the podium earlier this year.  

After winning 22 consecutive games (and still winning) by an astounding average margin of $64,913, one question must be asked: had every one of the show’s contestants been playing the wrong way?

Perhaps. Indeed, Holzhauer, “a professional sports gambler from Nevada,” may have shown the world what’s possible when a player template—never challenged or questioned over a half century—is blown up and replaced by another strategy that produces vastly superior results.

By now, millions [1] of Americans are familiar with Holzhauer’s unorthodox Jeopardy! strategy (the show is seeing ratings not reached since 2005). It’s actually quite simple: unlike 99.9 percent of the game’s previous contestants, Holzhauer starts at the bottom of the board—where the biggest money is—and goes sideways.


“It seems pretty simple to me: If you want more money, start with the bigger-money clues,”Holzhauer explained in an interview with Vulture magazine [2]. He told NPR, [3] “What I do that’s different than anyone who came before me is I will try to build the pot first” before seeking out the game’s Daily Doubles. From there, he “leverages” his winnings with “strategically aggressive” wagers (read: wagers far larger than any contestant before him was willing to make).

This strategy—along with the fact he’s answering 96.7 percent of the clues correctly—has allowed Holzhauer to build insurmountable leads heading into Final Jeopardy. With overwhelming leads, he can be ultra-aggressive with his Final Jeopardy wagers—one he made amounted to $60,013. It was that wager that allowed Holzhauer to establish his current all-time record total of $131,016. (He now holds the top 12 [4] all-time records for one-game winnings.)

In 22 episodes, Holzhauer has earned $1.69 million. Given that each show takes about 24 minutes to play, he’s averaging $192,045 an hour.

How could a strategy that really is “pretty simple”—one that on a per hour basis generates more income than any job in America—have been eschewed by approximately 25,000 previous contestants?

There are several possible answers to this question, none of which speaks particularly well of America, or Americans.

One is that most people are afraid to challenge the conventional wisdom. If something has been done the same way for decades by everyone, no one thinks that it can be done differently. That’s especially true if those who do challenge the status quo aren’t celebrated but excoriated. [5] 

Holzhauer’s contrarian approach to Jeopardy! has clearly rubbed many Americans the wrong way.

Washington Post columnist Charles Lane labeled him a “menace [6]” who is guilty of violating the “unwritten rules of the game,” a view endorsed by CNN host Michael Smerconish [7].

Other pundits have accused Holzhauer of using tactics that are “unfair.” [8] He’s been called divisive, polarizing, and controversial, someone who has “destroyed the quaintness of the game” and given America “deadly dull television.” Some speculate that he’s “gaming the system,” perhaps even cheating. Message board posters have pledged to boycott the show until the “robotic” Holzhauer is defeated.

Thankfully, the opposite view—held by slightly more Americans, if message boards are a gauge—is that James is a sensation whose accomplishments should be celebrated. According to one story, he’s the “man who solved ‘Jeopardy!’ [9]

Another depressing possibility is that the overwhelming percentage of Jeopardy contestants (and, symbolically, the population writ large) is incapable of contrarian analysis or of approaching a problem or puzzle in a unique way. Americans have either known for decades that the game was being played the wrong way but were too chicken to play it correctly, or James Holzhauer is the only American who’s figured the game out.

It’s too soon to tell whether future contestants will emulate Holzhauer’s strategy. For what it’s worth, over the past two weeks, 16 contestants have competed in Jeopardy’s “Teacher Tournament” and every contestant has reverted to the game’s normal style of play. Such is the enduring power of conformity, of conventional wisdom.

But what if the conventional wisdom is wrong? And how often is it wrong?

According to Washington Post columnist Robert Samuelson, the answer is “almost always.”

Samuelson wrote an important if largely overlooked book [10] on this very subject in 2001. The book’s title: Untruth: How The Conventional Wisdom is (Almost Always) Wrong.

Samuelson’s thesis is that people and organizations with an “agenda” often create problems that are either exaggerated or not problems at all. And the solutions policymakers give us to resolve these “crises” typically make things worse.

One can take his premise and run with it. Examples of when conventional wisdom has been wrong are abundant in the fields of science, health, economics, and education. We see it in our aggressive war policies overseas. We see it in our approach to presidential politics, at least before Donald Trump “broke” it. At this level, disproving the postulate that there’s only one way to play Jeopardy! might not seem like a big deal. It could be, however, if it opens the floodgates of independent thought among Americans.

Interestingly, as I was researching Holzhauer, I was able to identify one of his sources of inspiration.

“Do you follow hot-dog eating?” Holzhauer asked a reporter with Vulture who questioned whether he had “broken” Jeopardy!.

“No. Can’t say I do,” the interviewer responded.

Holzhauer: “About a decade ago, nobody ever thought someone could eat more than, like, 25 hot dogs in ten minutes. But this guy named Takeru Kobayashi came along and he shattered the record by so much that people realized there was a new blueprint to do this.”

So it wasn’t Secretariat winning by 31 lengths, or Bob Beamon breaking the long-jump record by almost 22 inches, or Wilt Chamberlain scoring 100 points in an NBA game who transcended what everyone thought was possible. Those athletes were simply doing the same things they’d always done, just far better than others.

The story of a 130-pound Japanese man with the goal of eating a mind-boggling number of hot dogs is what cracked the code.

Through intense study and trial-and-error experimentation, Kobayashi discovered two techniques no previous hot dog-eating champion had ever used. He quickly concluded that not only could he beat their records, he could blow them away.

He found that if he ripped the hot dog in two, squeezed each piece into a ball, dipped the balls in water (thereby breaking down the starch), squeezed out the excess water, and tossed each ball into his mouth, his stomach could tolerate many more dogs. The game-changing innovation helped Kobayashi double the existing record his first time out.

But here’s the kicker, one that offers hope for the world. Once Kobayashi smashed the record, his fellow competitors didn’t quit. They didn’t demand that the rules be changed. They simply adapted their techniques and raised the level of their game. Today, an American once again holds the hot dog-eating record [11]—72 wieners in 10 minutes!

The lesson is as obvious as Kobayashi’s bulging abdomen. When someone does think outside the box, when someone proves that performances once thought impossible are in fact obtainable, new levels of excellence become reachable.

When cancer is finally cured, my wager is it will be thanks to someone like James Holzhauer or Takeru Kobayashi. It will be someone who looks at all the work that’s come before him and says, “This doesn’t make sense. There’s a better way to approach this.”

Over the last two months, Holzhauer has been trying to teach Americans that eye-opening accomplishments are possible if one ignores or rejects conventional wisdom. The more Americans who absorb that lesson, the better.

“I’d be interested to see if there was a new paradigm in [Jeopardy!],”Holzhauer told Vulture. “If someone comes along and breaks my record, and attributed it to my style, that would be really great.” 

Bill Rice Jr. is a freelance writer in Troy, Alabama. He can be reached at [email protected]

26 Comments (Open | Close)

26 Comments To "How One Contrarian ‘Broke’ Jeopardy! and Won $1.7 Million"

#1 Comment By Dan Stewart On May 15, 2019 @ 1:29 pm

It’s not at all surprising that a group of teachers would ignore a wildly successful strategy and continue with the failed conventional approach.

#2 Comment By Joshua Ruark On May 15, 2019 @ 1:51 pm

While I find your analysis intriguing, I don’t think the reason for James’ success is his willingness to break with convention while others are content to stick with it. I believe the key to his success is his fearlessness. As you pointed out, he answers correctly over 95% of the time, so the large gambles on the Daily Doubles is not as high a risk as others might perceive. He one time he almost got beaten was when another competitor split the daily doubles and James got one wrong if memory serves.

There is an advantage to working down the category, as those questions can be eliminated from the realm of possibility James doesn’t have to worry about that with his knowledge base, so he can build his bankroll quickly before finding the DD’s in the round. There are times he hits it with the first question, and that slows him down a little but not too much

#3 Comment By Dontknowtheanswer On May 15, 2019 @ 3:43 pm

I always wondered why people didnt start at the bottom of the matrix….

#4 Comment By Kent On May 15, 2019 @ 4:05 pm

Great story. My regular day job is consulting on business process improvement. The conventional way we do things is almost always wrong. But change is incredibly hard, because people have vested interests in the current convention. I can’t tell you how many times I can show folks a way to solve a problem very simply, that cuts hours or days out of a process and they simply never imagined it. At first they’re thunderstruck and giddy at the idea, then they think about it for awhile, then they tell me it’ll never fly because the boss’s daughter wouldn’t get to flirt with the cute guy down the hall as often, or some such.

#5 Comment By Hmmm On May 15, 2019 @ 4:19 pm

I don’t know. I haven’t seen any of this guy’s games, but I used to watch the show. It seems to me that the bottom line must be that he knows most of the answers and is fast with the buzzer (the latter skill is often overlooked). By picking the high values first, and betting big on the daily doubles, he increases his odds of having twice as much money as the next player in Final Jeopardy, thus guaranteeing a win. That’s where the real advantage of his method lies — leaving nothing up to chance in Final Jeopardy. But he doesn’t get to apply his method if he doesn’t buzz first and get the question right in order to get to choose the next question. Bottom line: either you’re good enough to win or you’re not.

#6 Comment By Jacob On May 15, 2019 @ 4:45 pm

Arthur Chu a few years ago broke the mold in some respects by actively hunting for DDs. James has just taken such strategies to their logical conclusion.

And as for the Teachers Tournament and no one adopting James’ strategies, the TT was probably filmed long before James’ episodes were televised.

#7 Comment By James On May 15, 2019 @ 6:48 pm

I saw him. It appeared to me that he did it by being waaaay on the spectrum. That dude is a walking poster child for the autism crisis in America.

#8 Comment By Christian G. On May 15, 2019 @ 7:09 pm

Enjoyed reading this. “When cancer is finally cured, my wager is it will be thanks to someone like James Holzhauer or Takeru Kobayashi.” A wise wager indeed. Science guys are smart, but naturally tend to be “inside-the-box” people. Breakthroughs begin with the imagination. Side note: it seems obvious that his winning strategy is only a winning one because of his 96.7% accuracy. This allows him the freedom to “gamble” (I don’t see a 3.3% loss rate as much of a gamble) and rack up the dollars quickly. For most players, it would just be a way to get deep in the hole quickly.

#9 Comment By Sid On May 15, 2019 @ 7:16 pm

Seems his strategy is to buzz first, before knowing what the answer is, and then figure out the question. He is betting that he has the knowledge to pull that off.

No strategy will work if you don’t have the knowledge; and any strategy will work if you do (and buzz first).

#10 Comment By Little Expressionless Animal On May 15, 2019 @ 10:15 pm

I agree with the larger premise that most people, organizations, countries, etc. stick with the sub-optimal conventional wisdom just because that’s what’s always been done, but Holzhauer is hardly the first one to buck the Jeopardy CW. Chuck Forrest was bouncing over the board way back in 1985. Since then, David Madden, Keith Williams, Roger Craig, Arthur Chu, Matt Jackson, and Alex Jacob, among many others, have used unconventional wagering and/or clue selection strategies to increase their advantage. Even some 0 time winners like myself have started at the bottom row, hunted for daily doubles, and made strategic wagers.

What sets James apart is that he is just really, really, really good at trivia. Perhaps the best to ever grace American quiz shows. Anyone who saw his 2014 appearance on GSN’s “The Chase” (which is basically just a straight question and answer format) knows his unconventional strategy is largely superfluous. His strategy helps him win bigger than he would otherwise, but he would still win big going the conventional route.

Ultimately Holzhauer is like if Secretariat, already naturally the fastest horse, figured out a new way to run that was faster than a gallup.

#11 Comment By Hibernian On May 15, 2019 @ 10:50 pm

I think an important part of this is that people with strong statistical skills and those with broad knowledge of the entire spectrum of knowledge, including the arts, politics, society, etc., are rarely the same people.

#12 Comment By Kristian On May 15, 2019 @ 11:51 pm

The things you write about “Americans” — “There are several possible answers to this question, none of which speaks particularly well of America, or Americans” — would apply just as well to people in general, maybe with some slight variation from population to population.

#13 Comment By Joshua Xanadu On May 16, 2019 @ 12:14 am

As someone mentioned before, the strategy first gain mainstream attention by Arthur Chu. James is just smarter on getting more answers right, but the clue selection strategy has been around since Chu. What James does bring to the innovation table is his off-screen comments about buzzer practice and reading children’s books, which I imagine many future Jeopardy! hopefuls will adopt now.

#14 Comment By Connecticut Farmer On May 16, 2019 @ 9:35 am

Whatchacall “thinking outside the box.” Einstein did that in 1905. The result was relativity–which revolutionized the way in which we view the physical universe, not to mention the concept of time. And, for good or for ill, the notion of “relativity” would spread outside the realm of science

#15 Comment By Deacon Blue On May 16, 2019 @ 9:54 am

James’s strategy has positive unintended consequences for him. It must overwhelm his opponents, who no doubt are extra nervous in their first game. As James sees it, his wagers are “safe” – as he’s pointed out his odds of answering a question correctly are much better than a coin-toss. In his field, sports betting, if you can beat the line just 54 percent of the time you can make a killing. He’s simply found a game where his “edge” is massive. In effect, he has “monetized” this edge and his skillset to the nth degree.

He’s also said that his “risky” strategy actually (if counterintuitively) reduces anxiety when he gets to the all-important Final Jeopardy round. Here most players can win or lose based on just one question. In 20 of his 22 games, James was so far ahead he couldn’t lose. So he had no pressure on his final wagers. To him, he’s eliminating the possibility a “bad bounce” can beat him at clutch time.

His strategy – even more than his encyclopedic knowledge – is what makes him special. He’s actually only answering one more question correctly per game than Ken Jennings (who won 74 consecutive games) did. And yet, per game, he’s winning $44,000 more than Jennings did.

To him, the purpose of the game is to win as much $ as possible.

By the way, James hasn’t really won $1.69 million. He’s won $1.06 million. Uncle Sam takes 37 percent ($625,000) off the top. And, as far as I know, the IRS hasn’t answered a single question correctly.

Question: “Who’s the IRS?”
Answer: “The biggest all-time winner in Jeopardy history.”

#16 Comment By Tough Tony On May 16, 2019 @ 10:30 am

I lived in Las Vegas for four years and spent many, many hours in the city’s poker rooms.

I can tell you that Las Vegas is full to the brim with contrarians like James. Professional gamblers are contrarians almost by definition, in fact. And for every professional who is successful in a specialty, like sports gambling in James’ case, there literally are hundreds, if not thousands, of contrarians who end up in the gutter, on a bus back to Palookaville, in a hospital, or in a morgue. For one lurid example of such a contrarian, I would point you to Stephen Paddock, who gained his 15 minutes of notoriety in Las Vegas a couple of Octobers ago.

All gamblers everywhere are happy for James, I assure you. He gives them hope, but that is far from an unmitigated blessing in my (informed) opinion.

#17 Comment By Johann On May 16, 2019 @ 10:50 am

His strategy works because he is a walking encyclopedia. It won’t work for anyone who is not a walking encyclopedia.

#18 Comment By Deacon Blue On May 16, 2019 @ 11:06 am

Re: Little Expressionless Animal’s point that some previous players had bucked conventional wisdom and used the same “strategies” James is using.

This is true. A handful have. But even this fact might make the author’s point. The players you mention were huge winners on the show, all-time greats. Still, at least 99 percent of the contestants who came after these standout players did not use the same approach.

So even if someone shows us we could be doing something a better way, we still don’t do it. Or 99 percent of us.

I expect that the vast majority of future contestants will NOT employ James’s game theory. The best and smartest – the one percent – probably will.

To beat someone like James, you probably have to employ this style of play. So maybe in the upcoming “Tournament of Champions” will see James’s style more often.

At the same time, contestants probably shouldn’t play a style that makes them uncomfortable. That’s another big edge James has – making big wagers doesn’t scare him. Plus, if you’ve noticed, he typically only goes “all in” in the game’s first round. If he misses and loses everything – which has happened four times – he knows he has plenty of time to rally.

Later in the game, he doesn’t risk everything on DD. Per a quote from the story, he’s “strategically aggressive.”

#19 Comment By Richard Parker On May 16, 2019 @ 2:16 pm

Alpha Zero, a software program, has done much the same for chess recently. Even the best human players have been playing the game all wrong. Mobility (particularly the bishop pair) over material at all costs.

#20 Comment By Wilfred On May 17, 2019 @ 9:31 am

Hibernian is right. Game shows mix academic-type questions (science, history, etc.) with “popular culture”-type questions (movies, sports).

If you were studying hard in school, you probably weren’t attuned to all the popular culture stuff, & vice-versa.

#21 Comment By Barry Black On May 17, 2019 @ 9:45 am

Also, it helps to have an encyclopedic knowledge of many subjects.

#22 Comment By Deacon Blue On May 17, 2019 @ 10:49 am

The hot-dog eating savant doubled the record in his “sport” first time out by thinking differently.

I can think of at least two examples in the sports world that are somewhat analogous:
Dick Fosbury inventing his “Fosbury Flop” in high-jumping. No one else had ever done this … and the guy wins the gold medal the first time he is in the (1968) Olympics. Now, of course, EVERY high jumper uses this technique.

Pete Gogolak – the first “soccer style” NFL (and college) football kicker. Through the mid ’60s, every kicker kicked straight on. Today, none do. Also, the conversion rate of the soccer style kickers is far superior to the previous “Status Quo” technique.

… But no one had doubled records almost immediately by using contrarian techniques until the hot-dog eating contrarian.  Until James, who has more than tripled the amount a typical “Jeopardy!” contestant wins on this show with his new “innovations.”  James is averaging $76,864/ per episode. The average winner, pre James, won $19,980 on the show.

Leave it to James to pick up on some “out-of-left-field” example. To me, the fact he did this is another example of his genius, or at least his contrarian bent of mind.

#23 Comment By Kent Richmond On May 17, 2019 @ 11:34 am

And don’t forget Babe Ruth. Before his time, the strategy was to push runners to the next base. The Babe rejected that approach, swung for the fences, and changed the game. Today the sabermetrics crowd is showing how right Ruth was.

#24 Comment By Sid Finster On May 17, 2019 @ 2:41 pm

If markets were as efficient as proponents of market economics claim, why did it take over 100 years to invent Moneyball?

#25 Comment By Deacon Blue On May 19, 2019 @ 7:41 am

Basketball Hall of Famer Rick Barry shooting free throws underhanded is an example of someone who defied conventional wisdom – and had spectacular results by doing it – and still no one emulated his technique.

Barry’s free throw percentage is 4th all-time. One year, he made just shy of 94 percent of the free throws he attempted. Still, the “granny style” of shooting free throws simply looks silly or “sissy” and so no players have followed his example.

Lesson: You can be a contrarian and be proven right and your example will still be ignored or dismissed.

I think of Ron Paul in the political field as perhaps analogous to Barry. His entire career was defined by challenging political wisdom. His predictions/policy proposals were usually proven to have been right, but still “the establishment” ignored, dismissed or derided him. In fact, we see those who have been spectacularly WRONG rewarded with the highest positions in government. Think Bolton and Pompeo. Compare their views and predictions of these Mideast wars to Paul’s. Did they suffer career damage from being spectacular wrong? No. The opposite.

So … following conventional wisdom that is wrong (and toxic) is still a good “career move.”

#26 Comment By Deacon Blue On May 19, 2019 @ 8:23 am

… Expanding on the Ron Paul analogy/example. Paul is probably an example that makes the author’s larger point. Yes, Paul’s willingness to challenge conventional wisdom didn’t exactly make him a “success” during his political career (he barely got 4 percent of the vote in his most successful bid for the presidency). Still, he will go down in history as a transformative candidate IF a future presidential candidate or political leader builds on Paul’s platform of views … and wins.

I think Paul himself viewed his presidential runs as an opportunity to influence future generations and candidates – as the best way to get his contrarian ideas “Out there.” That is, he knew he was not going to win. But he ran anyway.

Even today, we see that views Paul held his entire career (that were long rejected as “radical”) are today becoming mainstream. Consider his view that marijuana use should be legalized. Thirty years ago, only maybe 2 percent of Americans would have held this view. Today, six or seven states have legalized its use, with more to come.

Paul also says/said that America’s “national defense” should be contained to protecting our own borders – not “Intervening” in countless other nations’ affairs. He says we should abolish The Fed. He says that real inflation is much higher than reported inflation. He thinks every governmental/Fed policy simply creates “artificial bubbles” that will burst, with terrible consequences.

If one day there is a major “reassessment” of Paul and his contrarian views – and more people come to believe he was right (and should not have been ignored or derided – his efforts in politics will not have been in vain.

It just takes one person – perhaps with more charisma or greater ability to “sell” his message – for smarter policies to be accepted, and detrimental policies to be rejected.

… The author could have also used the example of Galileo, someone who was indicted and imprisoned during his times, but who is now considered one of the most important figures in world history. If Galileo didn’t challenge conventional wisdom no one did.

If just one person working in the right field is strongly influenced by Holzhauer’s example that thinking outside the box can payoff big time, great changes could indeed be possible.