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Who Will Win the ‘Jeopardy! The Greatest of All Time’ Tournament?

On Tuesday night, James Holzhauer, Ken Jennings, and Brad Rutter will begin a multiday, prime-time battle of the brains. How will the contest work? And how will each of the participants gain an edge?

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The Jeopardy! gods are just. They heard our cries for order, our need to replace the horrors of subjective reasoning with cold, hard, quantitative certainty. Who is the greatest Jeopardy! contestant of all time? Well, the answer to that question won’t just be debated on Reddit and JBoard anymore. The immortal judges seated just to the left of the great celestial stage have seen fit to make a definitive ruling, replacing opinion (fickle, messy, difficult to put in a trivia question) once and for all with glorious, pure, highly testable fact.

On Tuesday, Jeopardy! will begin airing a first-of-its-kind “Greatest of All Time” tournament, pairing Brad Rutter (the all-time winningest Jeopardy! contestant, who has won an unparalleled five previous tournaments and never been defeated by a human opponent), Ken Jennings (whose 74-game streak during his initial 2004 appearance remains perhaps the most astonishing feat in the game show’s history), and James Holzhauer (who nearly equaled Jennings’s total prize money in less than half the number of games, and has since won the Tournament of Champions).

It is Jordan vs. LeBron vs. Kareem; Ruth vs. Mays vs. Aaron; The Last Jedi vs. The Last Jedi vs. The Last Jedi. A million dollars hangs in the balance. But before we get to the games and have the ever-loving gyrification beaten out of us, let’s go through the basics. How is this tournament going to be structured, how do you plan for playing the best minds in Jeopardy! history, and—no big deal—who’s likeliest to win?

The Format

The GOAT tournament, which begins Tuesday, will play out more or less like a best-of-seven sporting championship. Each evening will consist of two back-to-back games. The winner of the night’s aggregate two games receives a point; the first player to receive three points wins the tournament, meaning the event could last anywhere from three to seven nights. The tournament is getting prime placement: Instead of Jeopardy!’s usual block, GOAT will air during prime time (8 p.m. ET) on ABC.

Harry Friedman, who has been the executive producer of both Jeopardy! and its sister show Wheel of Fortune for the past 25 years, is retiring this spring when the current season finishes taping. GOAT is effectively Friedman’s last hurrah before Mike Richards, a veteran of The Price Is Right and Let’s Make a Deal, takes over as EP this summer: “This is his bookend,” says Cory Anotado, the founder of the game-show-focused Buzzer Blog.

Anotado says that GOAT is in keeping with Friedman’s ethos. “He’s responsible for making the show exactly what it is today,” he says. As EP, Friedman has pushed an otherwise staid show in new directions and toward new audiences, with tournaments like this one, doubling the dollar values of clues in 2001, and getting the show onto streaming platforms like Netflix, where it has found an eager audience of cord-cutters.

“There are very few game shows that have such a high level of play that you could convince a network to show a bunch of people doing the same thing” over and over, says Anotado. “Jeopardy! is a very sport-like game.”

How Do You Beat Brad and Ken?

Jennings has gotten attention for, as he joked recently, always being the “Bradsmaid”: He’s lost to Rutter in each tournament they’ve played. The two have faced one another head-to-head on nine occasions: Three times in the finals of the 2005 Ultimate Tournament of Champions, twice in the 2011 IBM Challenge (a.k.a. the Watson showdown), twice in the finals of the 2014 Battle of the Decades, and twice in the finals of the 2019 All-Star Games. In seven of those nine outings, Rutter has come out on top. Rutter has taken home the grand prize in three of the four tournaments they’ve faced off in—everything but the IBM Challenge, when Watson steamrollered to victory and Rutter came in third.

But perhaps more notable is their combined ability to lay waste to other challengers: They’ve finished in first and second place in every single one of the seven games in which they faced a human competitor.

Three players have had the luck and/or misfortune to join Jennings and Rutter in a game: Jerome Vered, Roger Craig, and Pam Mueller. All are überdominant players in their own right—Vered was a Tournament of Champions runner-up before making it to the Ultimate Tournament of Champions finals; Craig long held the record for highest single-game winnings with $77,000 (thanks for nothing, James Holzhauer) and won the subsequent Tournament of Champions; and Mueller, originally the 2000 college champion, has gone deep in four subsequent tournaments. All have hard-won places in the Jeopardy! pantheon—and all have found themselves coming in third to Jennings and Rutter. (Some good news, maybe: The GOAT tournament is going to send the second- and third-place finishers home with the same prize—$250,000.)

“A lot of people are like, ‘Oh, my god, you were going up against Ken and Brad. How could you even do that? Weren’t you just petrified?’” says Mueller. “And I say, ‘Well, that would’ve been a really bad way to go into the game.’”

Heading into her matchup with Jennings and Rutter in the finals of the 2019 All-Star Games, Mueller knew that her biggest challenge would be the buzzer. Rutter and Jennings are famously good at boxing out the competition by ringing in first—a largely unseen but vitally important element of Jeopardy! game play. Jennings, for example, beat his opponents to the buzzer an astonishing 61.45 percent of the time during his original 75-game run. (Brad’s lifetime percentage, 42.71 percent, is misleadingly low, because he’s mostly played in tournaments—more on that later.) And the duo isn’t just better than the average opponent—they’re also better than other very good Jeopardy! players. The current reigning champion, Karen Farrell, is in the midst of a thrilling win streak—but through Friday, her seventh victory, she rang in first only 39.89 percent of the time. (Holzhauer, also renowned for his buzzer abilities, rang in first 57.81 percent of the time during his initial streak.)

Buzzer timing on Jeopardy! requires finding a narrow window after host Alex Trebek has finished reading the clue and a nearby staffer has manually activated the signaling devices; buzz too early, and you’ll be locked out for a likely decisive quarter-second. Mueller, who had effectively played against Rutter in an earlier round of the All-Star tournament when he came in a distant third, managed her performance by trying to anticipate her opponent’s buzz times. And while Rutter and Jennings are both fond of self-deprecatingly pointing to their age as a hindrance—Rutter is 41 and Jennings is 45, with their initial runs 20 and 15 years ago, respectively—Jennings told me last year that he doubted age had much influence on buzzer timing.

“There’s very little speed involved in pressing the button. It’s not a first-person shooter,” Jennings said at the time—the day after Tiger Woods won the 2019 Masters, incidentally. “It’s much more like golf where you could see a 40-year-old with a back injury win occasionally because it really is just all about the timing more than the muscles.”

Mueller witnessed as much: She fell in both rounds to Rutter and Jennings during the All-Star Games, unable to find the window before the pair buzzed in. “It may be that they’re both so quick that there’s barely a gap to fit into,” says Mueller.

She says she once asked Rutter what the secret to his timing is. “If I knew what I was doing,” Mueller says he told her, “I could have made a lot more money selling that skill to others than I ever have on Jeopardy!” (With the help of tournaments, he’s made $4,688,436 on Jeopardy!, the most in the game show’s history, so take from that what you will.)

Roger Craig came as close as anyone has to toppling Rutter and Jennings, facing them in the two-game final of the Battle of the Decades. In both games, Craig pushed to a lead and then located a Daily Double. Both times in the Battle of the Decades, he had $10,200 in the bank. Both times, he chose to make it a true Daily Double. Both times, he was wrong.

Craig had made bold wagers because he, like Mueller, had worried about countering Rutter and Jennings on the buzzer. But he knew he’d have to make other adjustments, as well. “I also thought because I’m maybe not as good at the buzzer as them, I would have to take more risky shots with the Daily Doubles,” says Craig. “And that’s what I ended up doing.”

While his aggressive strategy ultimately cost him both wins and very possibly the tournament (and its $1 million grand prize; as second runner-up, he got a comparatively paltry $50,000), Craig’s strategy—hunt for Daily Doubles; go all in when possible—might be seen as a blueprint for beating Jennings and Rutter.

Perhaps this sounds familiar. If any player is known for that strategy, it’s Holzhauer, who—playing off his day job as a professional gambler in Las Vegas—made it a signature move to push all his “chips” forward whenever he found a Daily Double, usually after frenetically searching for it along the bottom of the game board.

How Do You Beat James?

The popular favorite to win the tournament is James Holzhauer, who last year stormed to Jeopardy! stardom. Whatever the influence of recency bias, there’s no denying Holzhauer’s absurd dominance: He cruised to an eye-popping $2.46 million last spring over a 32-game win streak, repeatedly breaking the one-day record thanks to his aggressive betting in Double and Final Jeopardy. In November, he returned to the Jeopardy! stage for the Tournament of Champions, taking the crown (er, belt) and the $250,000 grand prize.

Holzhauer is emblematic of the “new” style of Jeopardy! game play, one characterized by clearing the highest-value clues first, regardless of category, and wagering large amounts of money wherever possible. And while Rutter and Jennings have both observed similar patterns in recent tournaments, it’s probably not their preferred way of playing.

Both players began their Jeopardy! careers with the top-down, one-category-at-a-time method that characterizes the “traditional” way of playing. Likewise, both have usually been much more cautious in their betting. Like Holzhauer, Jennings found plenty of Daily Doubles during his initial streak, but he was significantly more conservative with them, betting an average of $3,265 through his first 33 games to Holzhauer’s $8,984. This difference in style adds up quickly in aggregate, which will matter more in a longer tournament like this one: While Jennings won himself $159,299 on Daily Doubles in that window, Holzhauer earned more than quadruple that amount ($654,416).

But while Holzhauer’s betting tendencies may have made him rich, Craig’s experience in the Battle of the Decades shows that going all in can easily be what dooms a player—even a very good one.

Yet Vered, the third player to face Rutter and Jennings, likes Holzhauer’s chances. “Roger bets insane,” Vered says, noting that Holzhauer is more conservative than Craig. “James only bets all in usually in the first round of Jeopardy, and then he bets big when he sees that losing would still give him the runaway. He’s never endangered a runaway once it was established.”

Then there’s the matter of age. While his and Rutter’s buzzer skills might not have slowed since they first went on the show, Jennings suggests that something else might have.

“Honestly, the thing that ages the most in your 40-something Jeopardy!-playing gentleman is just the recall of facts,” Jennings told me. “At some point you move into the age where you’re like”—he mimicked trying to remember a name—“‘Oh right, no no no, from that show, I think she was on that show with Brooke Shields.’ Everybody does that, but me and Brad, when we were younger, we did not do that. We could remember stuff that we had heard once.”

The Verdict

Imagine if instead of seeing Rutter, Jennings, and Holzhauer play somewhere between six and 14 games, depending on how many nights the tournament lasts, we could see them play … 1 million games. Who would win? Also: Who would dehydration claim first? Would anyone get scurvy? Would the audience pull a Donner Party?

We have a pretty good answer to one of those questions: Andy Saunders, who runs The Jeopardy! Fan, built a statistical model that uses data as varied as their answer histories, betting patterns, opponent skill, and the slight shifts in difficulty between different seasons of the show.

That model predicts that Rutter will win—kind of. The prediction had Rutter winning the, er, best-of-a-million GOAT tournament 36.118 percent of the time, Holzhauer 32.809 percent of the time, and Jennings a measly 31.073 percent of the time. Because the vast majority of Rutter’s victories have taken place in tournaments—unlike Jennings and Holzhauer, he didn’t start with a lengthy run in regular-season Jeopardy!—the model credits him for having a higher-than-average level of opponent across most of his Jeopardy! career.

But that’s still just the slightest of edges for Rutter, particularly when extrapolated back down to a mere seven-game tournament. The three players, in short, have strikingly similar skill levels.

Saunders says he’s just excited to watch. With the tournament in prime time, this marks the first time in the social media era that Jeopardy! will be on for everyone simultaneously. “You’ve never really had that massive shared experience of fans watching it at the same time.”