this! is! a winner!

How Emma Boettcher’s ‘Whimsical’ Jeopardy! Strategy Defeated James Holzhauer

Photo: Jeopardy!

Just when we thought James Holzhauer was going to conquer the all-time Jeopardy! winnings records with his signature mix of megabets and awkward smiles, in walks Emma Boettcher, the ultimate mental samurai, ready to fight him with her proverbial sword and shield of knowledge. Such an epic battle occurred on Jeopardy! Monday evening, when Boettcher — a user-experience librarian at the University of Chicago — defeated Holzhauer in a very tight game, which ultimately came down to the duo’s Final Jeopardy wagers and Shakespearian-history prowess. Boettcher walked away with a cool $46,801 compared to Holzhauer’s second-place $24,799 finish, casually ending one of the most historic streaks in the show’s history.

Prior to the episode airing, Vulture gave Boettcher a call to learn everything about her stunning win, which occurred in mid-March, from her strategy, to the psychology of wagering, to how she celebrated.

Prior to tonight, had your friends and family caught on to the fact you’d probably be facing James, knowing when you flew out to tape the show?
I’d say it was only recently that they realized what was going on. Besides James having a huge breakout moment for the show, sadly, a lot of people I know aren’t big Jeopardy! fans.

Aw, boo.
I know! What are they thinking?! Sometimes people will be around me and say, “Oh, I saw this article about this guy on Jeopardy!,” and they didn’t necessarily connect that this person could still be winning by the time I got on the show. But it’s been fun watching people get excited about it, just by virtue of James being such a great champion.

Tell me a little about yourself. What motivated you to try out for Jeopardy!?
Funny enough, I first auditioned for the show when I was a senior in high school. It was for the college tournament, since I was going to be a freshman in college by the time they filmed. So, that didn’t work out. [Laughs.]

Hey, it was a real blessing in disguise.
Truly. I was much too awkward to be on the show. Now, I’m not sure that’s changed really. [Laughs] I’ve always loved trivia. It’s how I found my people again and again, all throughout school. Academic contests were one of my favorite activities. Finding people to sit down and answer a few questions with is what I consider home, in a lot of ways. Watching Jeopardy! and trying to get on the show is a natural outgrowth of that. When I auditioned for the first time, I was hooked on the audition process. It was a lot of fun, which sounds extremely nerdy, since it’s like, you get to take a 50-clue test and then play a mock game! The auditions themselves are pretty fun. You really see how Jeopardy! brings together every type person from around the country.

Before you knew you would be facing James, what goals or strategies did you have in mind?
When I got the call to be on the show, I really wanted to hold my own. I wanted to be able to say I got onstage and I was able to put this lifelong love of trivia to good use. It didn’t necessarily mean I would win — there’s skill and luck involved in every game. I wanted to do right by that love of Jeopardy! The sillier goals are things like, If I had the opportunity, I’d give a shout-out to the MC of my high school academic competition, and other people who’ve informed my life.

For strategies, I’ve been watching the show for a while, and there have been some competitive champions over the years. They go hunting for Daily Doubles or they bet big in categories they’re really comfortable in. I wouldn’t say I executed this perfectly, but the Daily Double hunting was something I thought of before taping the show. When I watch the show, I often make a little grid of the board on a piece of paper and mark off what clues I got right and wrong. So when I got the call, I had all of this data in front of me, so I could be like, When it turns out the Daily Double is in this row, I have such-and-such chance of getting it correct, as opposed to this row. I was pretty well informed of my own abilities and knew where I could be confident and where I could be cautious.

I also simulated the experience of playing on the show as close as I could from home. I put my television in one corner and stood as far away from it as possible. Sometimes I used a pen as a makeshift buzzer, and sometimes I used a toilet-paper holder. It’s not a close representation, but it’s the best I could do in anticipation.

Did your career as a user-experience librarian help inform your strategy in any way?
When I was getting my master’s degree in information sciences, I wrote my master’s paper on Jeopardy! I don’t think being a librarian uniquely prepares me for such a game show, but I’m in an environment that really values knowledge. No question is too small, and no research avenue is too weird or unheard of. You’re around a lot of people who are fascinated by everything. It’s such a great place to be in to keep that love of learning going all the time.

What was your paper’s title?
Oh God, I can’t even remember the title. I stayed away from “This! Is!” puns. [Laughs] I opted for a slightly more academic title in the end, alas. The question I started out with was, How do people perceive what’s difficult, and how can we train a computer to make those same types of predictions? The Jeopardy! board values its clues going from top to bottom. I was parsing the text of those clues for length, the words used in each, the syntax, and whether or not they linked out to audiovisual materials. I gave all of that information to a machine learning tool and said, If I gave someone just words, is it better than giving someone just length? If I gave someone just audiovisuals, would that be better than having no information at all? I was very lucky to find an adviser who completely went with it.

When you flew out for the taping, how familiar with James were you when you were informed he’d be your competitor?
I was informed a little later on in the morning. When I got to the studio, I personally hadn’t heard of James before. The show keeps things under wraps pretty tightly, even for future contestants. We were sitting around a table filling out paperwork and doing things like that, and somewhere in the course of the morning a contestant coordinator pointed out James and said, “Here’s our returning champion, he’s won 29 games, and he’s won $2 million, but anyway, here’s more paperwork for you.” There’s a lot of information coming at you quickly, and that was one data point I had to deal with.

What was your initial reaction? Was there any Oh, shit moment?
My first reaction was that I honestly didn’t think it was a real number. I thought they were playing a joke on us — like, giving us a really big number at first and then giving us a lower number afterwards to make us feel relieved. Obviously that wasn’t true. [Laughs] I thought, Of course that’s the real number, just my luck. I was trying so hard not to dwell on it at that point. I talked to a few former Jeopardy! contestants heading in, and the best piece of advice I got was that I had to be comfortable with the surreal. It was going to be a weird experience, just go with it. They didn’t know my particular set of circumstances, of course, but it was surreal indeed. I tried to think about literally anything else. I had the advantage of playing in Monday’s game, which is the first game to tape of the day. So I didn’t see him play. I can’t imagine what it would’ve been like if I had to watch him on a roll beforehand.

When the taping began, what was your thought process like to beat this guy? Did you tweak your initial strategy at all?
I didn’t have the presence of mind to tweak things. [Laughs] After the first couple of clues, I had gotten some right, and my heart was pounding. I was surprised in myself. I thought I would be more chill about it, but I was wrong. Early on, I had to stop taking everything in and focus on every single clue, respond to it if I could, and if I couldn’t, go to the next one like an assembly line. I had to force myself to stay in the zone and stay pretty unemotional about it. That’s not necessarily because of James in particular, even though I knew he was good because of his numbers. It was more of a function of, I wanted to be on this show for so long, now it’s happening. Answer the clues, and oh my God, Alex Trebek is here. I didn’t focus on anything except playing the game.

James has described his gameplay strategy as being “strategically aggressive.” Did you feel you needed to adapt to this strategy in order to defeat him?
I pretty much did what I planned to do when I came in, to be honest, which was to jump around the board a little bit so the higher-value clues were taken care of first. As far as if I was “strategically aggressive,” I know it’s definitely a controversial strategy. Aggressive is an interesting word. It kind of implies you’re trying to throw off your opponent. It’s something you do to catch them off guard as opposed to stocking up things for yourself. I very much respected the other contestants I met that day, and I like to think I wasn’t deliberately trying to undercut them. But yeah, I knew jumping around the board was a tried and true success on the show. Let’s put it that way.

If you had to define your strategy in a non-aggressive way, how would you describe it?
It was a little bit whimsical. If I had to compare it to James — where it was more systematic — I was jumping around the board or staying in a particular category just because I liked it and felt like I was on a roll. I was a little more guided by intuition and feeling as opposed to having sussed out the exact, optimal strategy beforehand and using that every single time. I had all this data going in from having watching the show for so long, and that was another part of it, too. I don’t think I would’ve been as confident doing what I did, going for the higher-value clues, if I didn’t have the knowledge for certain rounds and certain rows to back it up. “Whimsical” and “data driven” probably don’t belong in the same sentence, but as a librarian, it makes me happy.

It was such a perfect nail-biter when you two were so close going into Final Jeopardy, especially when you factor in James’s professional background of being a sports gambler with years of wagering experience. Can you talk about the psychology behind why you chose to wager what you did? And why do you think he wagered so conservatively?
His conservative wager would’ve served him fairly well if I got the clue wrong. If you’re in second place going into Final Jeopardy, that’s what you need to be looking at. I can’t speculate on why he did what he did, but I will say that’s exactly what I would’ve done in that situation — staying ahead of third place but enough to cover me if the other person got it wrong. I wagered as large as I did because our scores were so close. Wagering isn’t something I’m terribly nuanced in, but I had a couple of options. The first was, assuming James was going to wager zero, and that third place — who played a great game, but unfortunately didn’t get any Daily Doubles and couldn’t catch up — wasn’t going to be a threat. I thought James was going to bet zero because that’s the logical thing to do in that situation. I thought, Do I have to wager anything at all? But when I saw that the category was Shakespeare-related … if there’s a dream category for me, it’s Shakespeare. James had been making so much money, and if he made a huge wager, I didn’t want to lose if I knew the correct response but didn’t wager enough to beat him. I figured I bet on myself knowing the answer, and wagered accordingly.

Did you have time to celebrate after the game, realizing the achievement you just made?
Not really. Jeopardy! tapes five shows a day, so I immediately became the returning champion and had to continue on. I didn’t have any opportunity to celebrate. I had to clamp down any energy I had and go right back into the zone to be totally focused to play the next game. But I was so happy. I invited my parents out to Los Angeles with me. My God, can you imagine if I hadn’t been able to talk to anyone about this at all since March? [Laughs] We found a very nice spot to have dinner afterward.

Did you and James get a chance to chat after this all went down?
We didn’t really talk after the episode. What people saw on television was pretty much all that happened — he came around to my podium and high-fived me, which was a wonderful gesture. After that, we chatted at the podium very briefly. I said I was so proud of us. But then I had to go on and play the next game, and James was out in the audience watching me play. He did send me an email a few weeks ago through the show’s production staff to say congratulations again and to give a bit of insight into what he learned with his time as a “news story.”

I hope you also got a high five from Alex Trebek.
I don’t recall, which is shocking. He was very congratulatory. You have to understand, that day was such a blur. A blur, but one of the best days ever.

How Emma Boettcher Defeated James Holzhauer on Jeopardy!