Back to All Articles

Welcome to Jeopardy Win Probabilities!

📧 This article was originally published on Substack. Subscribe there to get new articles delivered to your inbox.

A couple of years ago, if you had asked me if I considered Jeopardy a sport, I would have considered the question at most a curious oddity. Then I went on the show.

At the very least, it’s an intense competition that’s a lot harder than playing at home on your couch (hot take, I know). It demands a particular blend of fundamental skills- a broad knowledge base, quick recall, manual dexterity and reflexes, an understanding of wagering and strategy- that have the added pressure of a national TV audience and the desire to call yourself a Jeopardy champion, a title nearly everyone on that stage has dreamed of since they were a kid. It’s also a title that most people who go on the show don’t get to claim: only 25% of Jeopardy contestants win at least one game. And participating in the show is exhausting, as any former contestant will tell you. The pressure, the mental fatigue, and the quick turnaround between games produces an environment that is stressful at best, and outright traumatizing at worst. I came away from the show having understood elite players even less. Their ability to string together multiple wins and maintain the stamina and ability to execute in the moment is incredibly impressive, and even if calling elite Jeopardy competitors “athletes” sounds like a little much, their accomplishments are still worthy of some genuine respect and admiration.

The preparation tactics and in-game strategies of these elite players have become more commonly known over the last couple years and adopted by subsequent contestants, which some people have characterized and/or lamented as the “professionalization” of Jeopardy. I understand why this might rub people the wrong way. Some viewers like a version of the show where it’s average people thrust on to a national stage to see how much stuff they know, and the idea of training for a competition like Jeopardy might go against what they see as the spirit of the show. I do get where that view is coming from: the subject matter is literally and definitionally trivial, so devoting any kind of serious preparation might seem unfair to people who just want to go on the show to have a fun experience and test how much they know. But ultimately, I disagree with that view. It’s a competition with a healthy amount of money and clout at stake, so as long as there are sufficient incentives to win (and it seems like that’s not changing any time soon), contestants will pursue all kinds of strategies and tactics that maximize their chances of winning. I don’t think it’s a bad thing that we still care about Jeopardy as an institution. All else being equal, I would prefer to live in a society that still cares about facts and truth, even if the subject matter can sometimes be frivolous. So if we still care about the show, it’s inevitable that contestants will explore any and all ways to win.

And make no mistake, there have never been more resources available to contestants to help them win that there are now. Former contestants have written detailed guides on how to prepare for their appearances. Tactics like buzzer speed training that used to be sources of edge are now table stakes. Players are pursuing optimal strategies with increasing frequency in the last five years. I tried my own approach before my appearance, and it remains one of the most energizing and exhilarating projects I have ever worked on. Is Jeopardy a sport? You can quibble with the exact definition and still decide it’s not, but at some point, if you look at the way the game is being prepared for and played, you’ll notice a whole lot of quacking.

One of the biggest changes in sports over the last 20 years is the rise of analytics around those sports designed to help answer the fundamental question that drives all of sports: who is going to win? If you’re reading this article, you’re probably here because this article is in conjunction with a new project of mine: jeopardywinprob.com, a site dedicated to trying to quantify that exact question by generating in-game win probabilities throughout each game of Jeopardy. This is an approach I’ve used before elsewhere, and one that’s proliferated to just about every mainstream sport by now. Some of you might even be sick of them by now- why do we need charts to watch sports, can’t we just enjoy a game on its own merits without trying to quantify every twist and turn? Part of the backlash against things like win probability is its adjacency to gambling, an industry I’ve also worked in, and I’m no stranger to seeing the downsides of the corrosive effects of making gambling a load bearing pillar of interest in a sport, a trend that I’m also not thrilled about seeing. But before our current gambling explosion, things like the growth of the Sloan Sports Analytics Conference and the Moneyball revolution in baseball were animated by more pure motives: understanding the drivers of success in a sport, how to derive success-maximizing strategies, and a genuine love of wanting to understand a game. This is why this site exists. I’ve loved understanding sports through numbers for over a decade now, but Jeopardy is the only “sport” I’ve played at a high level that I’ve also analyzed through the lens of win probability.

Part of the motivation for this site existing is to understand my own time on the Alex Trebek Stage to retroactively answer questions about how I did and what I could have done better (something literally every contestant goes through)- not because I have any big regrets about how I did, but because I think they’re interesting questions to answer on their own. Jeopardy, independent of being an American cultural institution, is also unique among trivia formats in its blend of reflexes, accuracy, and strategy, a blend that I think is worthy of unpacking and dissecting. What strategies maximize a contestant’s win probability? Are different strategies needed for the new postseason tournaments the show is beginning to incorporate? Does a game that trends towards optimal strategy make a more compelling entertainment product, or can we explore potential variations to make a more exciting game? These are all interesting questions to answer in a vacuum, but also ones I feel a much more personal connection to: I got to be part of a cultural institution I have a lot of love for, and I hope that it continues to flourish. There are plenty of ways to do that, and my hope is that understanding Jeopardy better through an analytical lens can help it broaden its appeal, either through expanding how we consume the game, driving new formats for the game, or all of the above. And if you made it this far, thanks for reading- there’s plenty more to come.

Subscribe now


Thanks for reading Colin's Substack! Subscribe for free to receive new posts and support my work.

Enjoy this article?

Subscribe to get new articles on Jeopardy strategy and analytics delivered to your inbox.