Winning the Jeopardy! Tournament Didn’t Make Ken Jennings the Greatest Player of All Time. The Way He Won It Did.

It could have come down to luck, but it didn’t.

Ken Jennings with the Greatest of All Time Jeopardy trophy.
Ken Jennings won the honor Tuesday. ABC/Eric McCandless

James Holzhauer turned Ken Jennings into the greatest Jeopardy! player of all time.

Jennings always had the potential—and based on his celebrity status following his 74-game winning streak, many assumed he already was the greatest. But a simple victory in the Greatest of All Time tournament, which Jennings clinched last night, would have been enough. It’s not just that Jennings took the title, rather, how he did it that offers the best argument for his supremacy.

Jeopardy! executive producer Harry Friedman explained that the GOAT tournament was designed to “settle the question” of who was the greatest human ever to pick up that signaling device. However, the format, while engaging and effective, was inadequately powered to determine a statistically valid winner. Oakland A’s general manager Billy Beane famously observed that making the playoffs was a matter of skill and execution, but “what happens after that is fucking luck.” Given how even the competition is at that level, the postseason is too small a sample size to definitely determine the best team.

That goes for the Jeopardy! GOAT tournament as well. With the show’s 36 years as regular-season play, there was little doubt that the three contenders—Jennings, Holzhauer, and Brad Rutter—deserved to be there. But a format in which the first to win three two-game matches took home the crown was just not enough to make the determination on a statistical basis alone. After two matches, Jennings and Holzhauer were tied 1–1 (Rutter seemed to be out of the running). Assuming Jennings and Holzhauer were evenly matched (which data suggest they were), it was a question of chance—especially who found the most Daily Doubles—which of them would go up 2–1. After he did, Jennings had a huge statistical advantage. The math was likely to play itself out, just as it does in the baseball World Series.

That analysis robs Jennings of a well-earned victory, though. And this is where Holzhauer’s style of play comes in. As I wrote last week, if Jennings was going to beat Holzhauer, he would need to play at a higher level than he had in the past and embrace aggressive and risky betting strategies. And that’s what he did. By the numbers, Jennings not only narrowly outplayed Holzhauer this week, but in comparison to his prior performances, he massively outplayed himself. Playing your best ever against the best ever is greatness defined.

Jennings’ performance on a clue-to-clue analysis offers perhaps the best support for his victory amounting to more than chance. His was frequently faster on the buzzer than both of his younger competitors, he excelled in various styles of clues, ranging from pure trivia to brain teasers. But he also seemed at times to have to really dig deep to find correct responses. (I don’t believe he was hamming it up for the cameras, Quiz Show style.) Jennings’ long pause before offering “Who is Imhotep?” in an early but crucial Daily Double in Game 1 of Match 4 was indicative. Even Alex Trebek commented that Jennings’ responses had come to often sound unsure, as if he were asking the show’s questions for real. The clue writers seemed to stretch these three contestants to their limit. And under the highest-pressure circumstances imaginable, Jennings repeatedly delivered.

More than that though, Jennings incorporated Holzhauer’s game (both his statistical accuracy and aggressive style of play) and, many times, proved his ability to dominate within that context. That was never a certainty. During Holzhauer’s winning streak last year, Jennings spoke publicly about Holzhauer’s incredible stomach for large wagers, often saying that he wasn’t sure he could play that way. But when the moment came, Jennings did precisely that.

Additionally, Jennings embraced the idea that Jeopardy! is a game to be won with aggressive, not defensive, play, something that Holzhauer more than any other player in history demonstrated. Part of game theory is knowing when to apply the correct strategy—including when to deviate from an otherwise winning aggressive style. Deep into the second game of the final match, in which Jennings was mounting a large lead (he’d won the first game by more than 30,000 points), he found a crucial Daily Double. For the first time in the entire tournament, Jennings deviated from what had become the unwavering standard of play, always betting the maximum allowed at that point in the game.

“There’s a case to be made for a small wager here,” he said. (“No there isn’t!” Holzhauer added ironically, because he also knew that for the first time in the tournament, a relatively small wager was in fact the correct strategy; his best hope for a comeback was for Jennings to make a costly error at that very moment.) Jennings wagered 5,000 points when he could have wagered up to 8,800. (He gave the correct response in any case.) Nevertheless, by the end of Double Jeopardy, Holzhauer had made a huge and almost unbelievable surge, and was leading the game by 21,000, by far the biggest lead enjoyed by any player going into Final Jeopardy in any of the eight games. Combining their scores with their earnings from the first match when considering his wager, Jennings once again executed the correct betting strategy—something that, I believe, he might not have done in a non-Holzhauer environment. He bet nothing! Here’s why that was a brilliant move.

Holzhauer led the game 44,000 to 23,000 going into Final Jeopardy. Jennings assumed that Holzhauer would get Final Jeopardy correct (he usually does) and that he’d risk it all—which he had to in order to overcome the deficit from the earlier game. If both assumptions proved true, Holzhauer would have ended up with 88,000 for the game. Even if Jennings did the same and racked up 46,000, Holzhauer would still win the two-game match (more than making up for the 31,419 point deficit from Game 1), tying the tournament at 2–2 and forcing another night of play. So the only circumstance in which Jennings could win the overall match and clinch the tournament Tuesday night was if Holzhauer bet it all and was wrong. In that case, Jennings simply needed to keep what he had already accumulated and he would win. That’s precisely what happened. The capstone was that Holzhauer missed a tough Final Jeopardy clue. Jennings nailed it.

True champions always say they want to win by beating the best. Up until this tournament, James Holzhauer was statistically and strategically the finest player in the game’s history. But Jennings rose to the occasion. By beating the best, and adopting a style of play that he was neither accustomed to nor comfortable with, Ken Jennings proved himself to truly be the greatest Jeopardy! player of all time.