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James Holzhauer, Ken Jennings, and Brad Rutter behind their podiums on Jeopardy! The Greatest of All Time
Ken Jennings on Jeopardy! The Greatest of All Time.
Photo: Eric McCandless/ABC

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Ken Jennings became Jeopardy!’s greatest player of all time. Now it’s time to move on.

We caught up with the champion to talk strategy

Matt Patches is an executive editor at Polygon. He has over 15 years of experience reporting on movies and TV, and reviewing pop culture.

Ken Jennings is the greatest Jeopardy! player of all time. He has a trophy and a million-dollar check to prove it.

In Tuesday night’s match, the fourth in a set of prime-time Jeopardy! specials, Jennings, a 45-year-old writer from Washington state, bested Brad Rutter and James Holzhauer to earn the GOAT title. He arrived to the tournament as a titan: In 2004, he won 74 consecutive games, a streak that imbued him with the glow of a trivia god. The money was huge — between his initial runs, subsequent invite-only tournaments, and this week’s new bounty, he’s earned over $4.5 million in winnings — but the cultural effect was bigger. In the years that followed, Jennings wrote books, magazine columns, and puzzles for any factoid-consuming fans who wanted to channel their inner Ken. Jeopardy! was part of his life.

Still, the Greatest of All Time championship offered something entirely new. Going up against Rutter, who beat him in the Battle of the Decades tournament in 2014, and Holzhauer, whose gameplay calculus turned him into Jeopardy!’s Joker, challenged Jennings’ skills and his legacy. Who could say no?

Polygon spoke to Jennings shortly after his big win to understand the pressure of the game, reflect on his Jeopardy! career, and wonder aloud if there’s more answer-questioning in the GOAT’s future.

Polygon: First off, congratulations.

Ken Jennings: Thank you so much. I watched it last night and it was great TV. I normally hate watching myself, but I have loved this tournament. Jeopardy! does a fantastic job.

What did you get out of watching?

I said I wasn’t going to watch it, and then my family kept having it on, and I kept finding myself getting sucked in because I’ve just been a Jeopardy! fan my whole life. Like, I’ve watched the show since I was 10 years old. It really has been very formative for me and my idea of what a smart person is like and how learning is important. And these were just well-paced, well-shot games in a well-thought-out format. I think they just knocked it out of the park. They’re a national treasure, and this was a real victory lap for Alex and the show. I had to watch.

ken jennings gasps between james and brad during the jeopardy! greatest of all time tournament
The moment of triumph for Jennings (center), between James Holzhauer (left) and Brad Rutter (right).
Photo: Eric McCandless/ABC

Was there a hesitation about coming back for this game? Putting your reputation on the line isn’t easy.

I actually said no. When they told me that they wanted the big showdown with me and James and Brad, I said, “No, I think I’m past my Jeopardy! prime.” And luckily, they talked me into it. I was very stressed about the whole thing, and then the game started and it all kind of washed away, because I love playing the game so much, and all those good memories came back. Brad and James were loose and fun, and it was a really great week, I think, win or lose, for all three of us.

How far ahead did you commit to the show? How long did you have to practice?

It was very shortly after James’ run, I got the call saying, “Hey, everybody wants to do this three-player showdown. We’re going to do it around Christmas.” And I thought, No, already?! Like, I thought I was out, but they pulled me back in. I had my Godfather Part III moment. That did give me a few months, and I knew who I was going to face — which was a real novelty for Jeopardy!; you normally don’t know who the finalists are going to be, but at this time I knew — so I could look at tapes. I could kind of scout out both players, and in particular, James — like, look at his game and see if there was a way to beat him. It turned out, the only way to beat James is to play just like him.

Watching the championship, it seemed clear that this was not how you played Jeopardy! during your original run.

Well, during my original streak, I just played one game at a time. My strategy was always just to get through this game, you know, to stay loose, have a good time, and keep it going. And that turned out to be a great strategy to rattle off a long streak — just to play like I do on my couch. But that wasn’t going to work against James Holzhauer. You’re going to need to hunt aggressively for Daily Doubles, and you’re going to have to bet huge on every opportunity that comes your way. Swing for the fences, and sometimes you’re going to miss, but it’s a best of seven, essentially, so swing for the fences and hope that you connect on a few.

So how did you prep for this tournament?

I watched a ton of James’ games, mostly just so I wouldn’t get intimidated. The secret of James’ success is just that he’s so dominating out of the gate that the other contestants just feel like they’ve lost by the first commercial. Like they beat themselves. And so a lot of it was just watching just to think, Hey, this is definitely going to happen. because this guy is scary as hell. Um, do not take yourself out of the game.

How important is your relationship to Alex to playing the game? Do you have an understanding of his vocal mannerisms?

Well, we all have that relationship, right? If you’re a Jeopardy! fan, he’s in your living room every night. Like, people really think of him as part of the family. And so I’ve heard his cadence for decades, and I feel like it’s built into my biology at this point, you know — it’s almost like your heartbeat or your brain waves. I know how he’s going to read the clue each time, and that’s what gives you the rhythm on the buzzer. So I watched a ton of Jeopardy! in preparation for this, just kind of getting back into the rhythm of his voice and trying to recapture that. In my original run, I felt like if I just followed that rhythm, I couldn’t be beat. Like, my thumb would just find the right second. I was just trying to get back into that happy place.

When does the buzzer actually allow you to ring in?

You can’t buzz as soon as you know it. You have to wait for Alex to finish reading the question. When he does, a human somewhere flips the switch, activating your buzzer. And if you buzz in early, before your buzzer’s activated, you get locked out for a fraction of a second. And of course, if you take too long, you get beat. So there is a very narrow window — maybe, like, a syllable or a half syllable after Alex finishes reading the question — where you want to buzz like crazy. You’ve just got to find that millisecond.

You possess a wealth of trivia knowledge, but suddenly, Jeopardy! is like shooting proton torpedoes into the Death Star. Do you have a background playing physical games that helps you with that coordination?

I have a background in being very competitive at games. I am not a huge video game gamer. I did kind of get very addicted to Mario Kart 64 in college, and I had very lousy grades for a semester. I tried to put the demon back in the bottle and stay away. But that’s the rising generation. That’s the James Holzhauer generation and the next generation of Jeopardy! players. They’re all going to be Nintendo-trained or PlayStation-trained.

Has James fundamentally disrupted how Jeopardy! will be played in the future?

Absolutely. I was on Jeopardy! for six months, and nothing I did, anyone will ever think of as a strategy to duplicate, because I’m just yelling out answers. But he had a thought-out approach that is amazing to me. He watched Jeopardy! and thought, For 35 years, people have been playing this wrong. I have an idea, but I’m just going to try it out on my first time on the stage. I’m just going to play the game a totally different way. And if you’re a very skilled, accurate player like he is, that’s just unstoppable. I think you’re going to see more strong players in Jeopardy! in the future, trying to play his way and winning big. And I think you’re going to see a few deluded players try to play his way and self-destruct.

ken jennings holds his jeopardy trophy next to alex trebek
Jennings celebrates with his GOAT trophy and Jeopardy! host Alex Trebek.
Photo: Eric McCandless/ABC

What category pops up on the board and makes you gulp?

Honestly, I’m a huge generalist. That’s the Jeopardy! secret: You have to know a little bit about everything. So even if it’s something I don’t love — even if it’s hockey, like, I know there’s going to be some approachable tip of the hockey iceberg where I’m going to be able to get some foothold on some of the clues. I love the wordplay stuff, but maybe I’m not great on, like, corporate-type stuff: business and industry, history of companies and consumer culture and all that. I’m not great. I’m also now at the age where pop music scares me. That’s why you have to be young on Jeopardy!. It’s not just buzzer thumb; you still need to know who Cardi B is.

Which brings us to an important question: Where did you learn “OK boomer” in order to employ it during the tournament?

Everyone knows “OK boomer”! I’ve been railing about the Baby Boomers my whole life. My kids are going to grow up on an underwater planet because of the Baby Boomers. I was not going to get beat to that.

Is there a question from your many runs on Jeopardy! that haunts you to this day?

I guess the hardest pill to swallow for me was the time I had the best chance at beating Brad, who cleaned my clock three times from the past, but I was one question away from beating him. And you had to name which secretaries of state were unmarried, and I guessed Madeleine Albright instead of Condoleezza Rice, and Brad came back and won that game. Just because I didn’t know enough about the love lives of U.S. secretaries of state. I still think about that sometimes on sleepless nights.

Your first record-breaking run on Jeopardy! changed your life by giving you the chance to shift occupations and own a reputation of being great at trivia. What will winning this tournament do for you?

I think it lets me move on. It always kind of bugged me that I kept finishing in second place in all these Jeopardy! tournaments, and that’s what kept me coming back for more. And I feel like now I can happily retire and become a happy ex-game show contestant. I did everything I set out to do on the show, I’m a little bit past my prime, and it’s time to hang up my spurs and my buzzer and ride off into the sunset.

Alex isn’t looking to retire, but in theory, Jeopardy! will go on without him. Would you ever come back to host?

Oh man. To me, I can’t even think about that question, because Alex is irreplaceable to me. He’s synonymous with the show. To answer that question, it would require thinking about a version of Jeopardy! without Alex Trebek, and I have not emotionally prepared for that. I mean, it would be very flattering, honestly. Obviously, that’s a dream job.

OK, so when can we expect you on Wheel of Fortune?

If my country needs me, yes, I will be on Wheel.

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