The Jeopardy! Greatest of All Time Tournament Has Turned Into a Dogfight

James Holzhauer changed the game, but Ken Jennings has proved he can play that game, too.

Holzhauer and Jennings smile from behind their podiums. Holzhauer has $32,400 on the board, and Jennings has $22,000.
James Holzhauer and Ken Jennings on Jeopardy! Eric McCandless via Getty Images

We are two matches into the Jeopardy! showdown between three of the most dominant players in the show’s history, and here’s what we know so far. The greatest player in Jeopardy! history is either James Holzhauer or Ken Jennings, currently tied at one match apiece. If Brad Rutter wins in the end, it will be one of the most remarkable comebacks in sports history. (Yes, Jeopardy! is a sport. Don’t @ me.)

That the competition has been fierce is actually somewhat of a surprise. Coming into the tournament, Holzhauer was a huge favorite to win.

This is the case for three reasons. First, the format essentially eliminates the biggest potential weakness in Holzhauer’s game: variance. During regular-season play, his large bet strategy came with what statisticians call a high “risk of ruin”; even though his large Daily Double bets usually paid off, if and when they did not, the downsides could have been potentially devastating. However, in the GOAT tournament, a player can not only lose a match without being eliminated—they can lose big and they’ll still be back for more.

In regular-season games, if you lose once, you’re a goner, and even in the typical three-round tournament format, Holzhauer’s style could be particularly risky. (Faced with a Daily Double deep into the first round game of the 2019 Tournament of Champions, he wagered a measly $1,109, knowing that if he failed to connect, he would not only risk losing the game but also a chance at a wild-card spot.) But in the GOAT format, the risk of ruin is essentially eliminated. If Holzhauer loses one match, it makes far less of an impact. He can just reboot and return to business as usual in the next match.

Second, conventional wisdom holds that Holzhauer’s strength is in his betting strategy while Jennings has the more comprehensive knowledge of trivia, but a side-by-side statistical comparison of regular-season games suggests that for the most part, Holzhauer’s gameplay was superior to Jennings’. This holds through virtually every numerical lens, including percent correct and incorrect responses, and percent correct on Daily Doubles and in Final Jeopardy. For Jennings to have any chance of defeating Holzhauer, he would not only have to adapt Holzhauer’s flashy betting style (something Jennings publicly said he might not have the stomach for)—he would also have to perform better clue-to-clue.

In the first two matches, Jennings has done just precisely that. We’re in a dead heat so far. Neither Jennings nor Holzhauer has missed a Daily Double, and both have wagered the maximum allowed (as has Rutter on his Daily Doubles). Jennings and Rutter have also incorporated Holzhauer’s gameplay, searching for Daily Doubles early by choosing more expensive (and harder) clues. Jennings even borrowed Holzhauer’s preferred terminology, favoring his “all in” over the classic “Let’s make it a true Daily Double.” Together, Holzhauer and Jennings have gone 7 for 8 on Final Jeopardy clues, which have been harder than almost any in the show’s 36-year history. (Jennings’ miss would not have changed the match’s outcome, as Holzhauer’s victory was mathematically assured going into the final round.)

The third advantage Holzhauer has is his age. At 36, his performance on the signaling device is likely to be a hair faster than either Rutter (41) or Jennings (45). Research suggests that even these modest age differences may amount to a few milliseconds’ advantage. But speed on Jeopardy! is not only a matter of reflexes. (Players can ring in as soon as Alex Trebek finishes reading a clue and a blue light in the studio illuminates; if you ring in early, you’re locked out for a second or two.) Watching for that blue light and anticipating it is much harder if you’re still processing the complex information coming from Trebek. Certainly faster information retrieval means a player can devote more of their cognitive burden to timing that buzzer, but it is harder to focus on that aspect of the game if you’re still trying to remember the name of a British prime minister in the 1960s, or piece together multiple pieces of information needed to come up with the correct response.

This is where Jeopardy! is more than just a test of trivia and speed. Jeopardy! clues are frequently brain teasers crafted by a team of gifted writers, full of winks and subtle hints that can steer astute and experienced players toward the correct answer. While that still favors the young overall, it is clear after two matches that Jennings’ mind continues to be a beautiful machine, capable of efficient synthesis under pressure. Jennings has beaten Holzhauer to the punch in many instances, so far, and narrowly leads on correct responses overall.

What’s also clear is that Holzhauer’s strategy has changed the game for the better and everyone is benefiting. If Jennings were playing his usual game, Holzhauer would be cleaning his clock right now. Instead, we are watching a dogfight unfold. Jennings is now playing Holzhauer’s game and proving that he can.

So what does this mean for everyone else? For a typical player trying Holzhauer’s approach, a huge one-day win is now more possible (with a little luck). Also, the stigma and shame of large bets backfiring have largely become things of the past, as most viewers now understand the game theory. (In years past, the goal of many challengers appeared to be avoiding disgrace first, and winning second.) The “Holzhauer game” is more interesting to watch. It is less predictable and creates more high-pressure moments.

With elite players like Jennings, utilizing Holzhauer’s style makes the game more exciting as well. It’s as fun to watch a player dominate the competition as it is to watch them try to salvage a win after a costly error or two. Whether Holzhauer’s style overall favors a dominant player’s ability to make a long run during regular-season play or whether it helps a challenger spoil such a run is hard to know now. We should know this in the coming season or two.

Who will ultimately win the tournament remains anyone’s guess. Each has his individual strengths. It looks as though, even at 45, Jennings may be better at making oblique connections and doing quick mental math. For example, during the second match, Jennings rang in with the correct response in the intimidating category “20-letter words” 4 out of 5 times (though he benefited from rare mistakes in the same category by both Holzhauer and Rutter). Holzhauer, on the other hand, may possess a slightly more prodigious memory bank, and may be a bit more facile recalling remote trivia. His correct response in the second game of match two of Final Jeopardy (which Jennings missed), essentially required encyclopedic knowledge. It was Watson-esque.

Given how closely matched Holzhauer and Jennings appear to be, the ultimate winner will come down to a combination of three things: performance under pressure (especially as it mounts), endurance, and luck. If the games continue as they have, the winner may simply depend on flukes like who finds the Daily Doubles (and when). If that’s the case—and this is sacrilege because Jeopardy! is a three-player game—we may need a much longer duel to determine the true GOAT. Would people watch a one-on-one Holzhauer-Jennings faceoff? I know I would.