How to Bet the Jeopardy! Greatest Of All Time Tournament

Retroactive Hint: Lay Odds on the Underdog

The Jeopardy! Greatest of All Time Tournament kicks off today as a Prime Time Television Event, the sort of thing the syndicated game show almost never does. It pits against one another the show’s three biggest money winners, Brad Rutter, Ken Jennings, and James Holzhauer, in a best-of-seven format that’ll air at 8/7c on ABC until one contestant wins three games. First prize is a cool million, and public interest in the tournament is likely to be sky-high; by the end of Holzhauer’s run in 2019, “Jeopardy!” ratings were up 24% year-over-year. Believe it or not, you could even bet on this, or at least you could before the shows were taped in early December. As of late November, offered the following odds:

James Holzhauer   -175

Brad Rutter   +175

Ken Jennings   +225

A quick primer on money-line odds: the books express these in variables of $100, so to bet on Holzhauer you’d wager $175 to win $100 – a $275 payout including the initial bet–and to bet Jennings you’d bet $100 to win $225. Holzhauer is a significant betting favorite. In other words, although this is what online bookmakers call a “special”; most bookmakers set the limit for how much you can wager on a special bet like this at a nominal sum like $50 or $100. No worries, then, that Holzhauer, a professional sports bettor, could possibly be in the tank.

So who’s actually likely to win? Here’s an attempt to handicap the field and provide some insight into the strengths and weaknesses of the three competitors.

Rutter Ball

When Rutter appeared on the show in 2000, the old rules still stipulated that a contestant could win no more than five games. Rutter won his five, then the 2001 Tournament of Champions, then the 2002 Million Dollar Masters, then the 2005 Ultimate Tournament of Champions, and so on. Most recently, his team won the 2019 Jeopardy! All-Star Games. The only blemish on his record was a 2011 loss to Watson, an IBM supercomputer, which easily defeated him and Jennings in an exhibition match. In 27 games over 19 years, Rutter has never lost to a human being on “Jeopardy!”

When you consider that most of the humans he did beat were legendary Jeopardy! super-champions, including a perfect 7-0 record against Jennings, the magnitude of his accomplishments becomes clear. His raw statistics are less impressive than Jennings’ or Holzhauer’s, but only because he’s played the vast majority of his “Jeopardy!” against the best of the best. If the Greatest of All Time Tournament boils down to speed and reaction time, as “Jeopardy!” so often does, there might not be a better buzzer game trivia player in the world than Brad Rutter.

Gee-Whiz Jennings

Jennings won 74 consecutive games in 2004, a streak that will likely never be equaled. The “Jeopardy!” schedule is deceptively punishing; the show usually tapes five games per day, two days a week, and there’s a bit of internal mythology around the fact that returning champions tend to lose on Fridays, when the fatigue of a long taping day has caught up with them. Jennings displayed a preternatural ability to endure the rigors of taping for so long that by the time he finally lost game 75, he was already a national celebrity.

In terms of sheer breadth of knowledge, neither Rutter nor Holzhauer can touch Jennings. He was a top college quiz bowl player at BYU and has an elite quiz bowl player’s comprehensive knowledge of a whole range of academic minutiae. If this were a quiz bowl competition, he’d be the heavy favorite.

But Jeopardy! is not quiz bowl, which employs a format that rewards one’s ability to parse incomplete clues and de-emphasizes pop culture and current events knowledge. By the standards of college quiz bowl, “Jeopardy!” material is incredibly pedestrian. One open question about the tournament is exactly what Trebek will ask, and how high they’ll scale the difficulty level–one would think it’ll be rather difficult, given the competition, but “Jeopardy!” writers forever need to balance esoterica with the comprehension of their audience. This is a game show that many viewers enjoy playing along with at home, after all. Yet if the material written for the tournament skews heavily academic, Jennings could have a major advantage.

Darth James

This leaves us with the question of Holzhauer, the least-known quantity of the three of them despite his recent run of sustained success. Because Jeopardy! has invited Rutter and Jennings back so often and they’ve played against each other so many times, we have a pretty good idea of their relative abilities in high-stakes tournaments. Holzhauer has his 32-game streak, numerous dazzlingly high single-game winnings records, and a victory in the 2019 Tournament of Champions, but he’s never faced players at this level.

What we know is that hunting Daily Doubles and wagering big are integral to his gameplay, and that he tries to put the game away before Final Jeopardy whenever possible. Holzhauer clearly has the best command of game theory and strategy of the three contestants, and he’s likely to be the best at identifying any unusual in-game inflection points that occur. He’s also almost certain to provoke adjustments in the other contestants’ playing styles, rather than the other way around; Rutter and Jennings are generally conservative when it comes to Daily Double wagers, which won’t be an optimal approach against Holzhauer.

Don’t expect six-figure wins from any of them; the $1,000,000 for first is much more than anyone could plausibly expect to win in three games. But should Holzhauer find the Daily Doubles, he’s generally more accurate; over time, he’s gotten 93% of his Daily Doubles correct, vs. 85% for Rutter and 83% for Jennings. These are all world-class numbers, but a missed Daily Double can easily be the difference between a win and a loss.

As far as the mythical betting lines are concerned, I think Rutter was a good value at +175; I would personally have him as a slight favorite vs. the field. Buzzer control is too important in a game that’s likely to swing on late Daily Doubles, and Rutter’s skills have held up against super-champions. While I wouldn’t expect his perfect record against carbon-based life forms to remain intact, there’ll be plenty of opportunities down the road to relitigate the “Greatest of All Time” title; once you’ve ascended to the highest echelon of Jeopardy! fame, there’s nothing to do but keep coming back.

Prediction: Rutter in six.

And if you’re one of the people who laid down your bet, with, apparently, inside leaked knowledge of who won these games taped in December, well, dinner’s on you.

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Daniel Cohen

Daniel Cohen is a software developer who lives in Syracuse, New York. He has written for Yard Work, The Guardian, and Maura Magazine.

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