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Inside Ken Jennings’ ‘Jeopardy! Greatest of All Time’ victory

When ‘Jeopardy!’ producers approached him last year about doing the ‘Greatest of All Time’ tournament, Ken Jennings figured he was past his prime or, in his words, ‘over the hill.’

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This image released by ABC shows contestant Ken Jennings with a trophy on “Jeopardy! The Greatest of All Time.” “Jeopardy!” ratings have dropped since Ken Jennings stopped hosting.

This image released by ABS shows contestant Ken Jennings with a trophy on “Jeopardy! The Greatest of All Time.” Jennings recently spoke with the Deseret News about the tournament.

Eric McCandless, ABC via Associated Press

Editor’s note: This is the first in a two-part series. The second article will focus on Ken Jennings’ new board game, “Half Truth,” due out May 6.

Ken Jennings didn’t want to do it. 

Not at first, at least. 

When “Jeopardy!” producers approached him last year about doing the “Greatest of All Time” tournament, Jennings figured he was past his prime or, in his words, “over the hill.”

He figured he’d played his best games in 2004, when he went on a 74-game winning spree and won $2.52 million. 

While “Jeopardy!” was the same show 15 years later, the game was different. Jennings had watched a professional sports gambler named James Holzhauer waltz onto the set and revolutionize the trivia game in 2019. 

Holzhauer didn’t stick with one category, gradually working his way from the easiest clue to the hardest clue. He attacked the game board. He started with the hardest, most valuable clues. He went from category to category stalking the Daily Doubles. And he bet big. 

The idea of the tournament stressed Jennings out. But the show’s producers talked him into it. 

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Ken Jennings won the “Jeopardy! The Greatest of All Time” tournament, which aired in January. Jennings recently spoke with the Deseret News about the tournament.

ABC

Soon after, Jennings found himself engulfed in Holzhauer footage. He watched tapes to pin down the player’s strategy — and to figure out how he could defend himself against that strategy. He listened to the cadences and inflections of Alex Trebek’s voice. 

But it was the night before the tournament, which was filmed in December, that Jennings had a real change of heart. 

“I had this sudden epiphany where I realized, ‘If this is going to be your last time playing ‘Jeopardy!’ just go enjoy it. It’s certainly going to be your last time playing with Alex (Trebek) there. Just enjoy every minute,’” Jennings recently told the Deseret News. “I kind of went out on that stage with that goal in mind, just to really have a good time.” 

Well, he had a really good time — to the tune of $1 million.

‘It was just a blast out there’

For a moment, though, let’s set aside the fact that Jennings emerged from the tournament the champion, walking away with $1 million and a large trophy engraved with the words “The Greatest of All Time.” (Don’t worry, we’ll come back to it.) 

That was obviously a huge moment for Jennings. But even more fun was getting to play trivia with Brad Rutter, his longtime friend, and Holzhauer — and finding little ways to banter while doing it.

During the second night of what would end up being a four-night event, Jennings had 8,400 points when he landed on a Daily Double. 

“I gotta do it, and I can do it with a clear conscience: 8,400, Alex,” Jennings told Trebek, wagering all of his points.

“But can you do it?” Trebek joked as he mimicked Holzhauer’s signature move of pushing in poker chips to indicate being “all in.” 

“Has James copyrighted this?” Jennings asked.

“One-time use only, you’re good,” Holzhauer quipped. 

“He now owns 10% of whatever you get,” Rutter told Jennings. 

In this image released by ABC, contestants, from left, James Holzhauer, Brad Rutter and Ken Jennings appear on the set of “Jeopardy!” in Los Angeles. The all-time top money winners; Rutter, Jennings and Holzhauer, competed in a rare prime-time edition of the TV quiz show “Jeopardy! The Greatest of All Time.” Now, that tournament is re-airing May 4-15.

In this image released by ABC, contestants, from left, James Holzhauer, Brad Rutter and Ken Jennings appear on the set of “Jeopardy!” in Los Angeles. Jennings recently spoke with the Deseret News about his victory on the “Jeopardy! The Greatest of All Time” tournament.

Eric McCandless, ABC via Associated Press

Miming Holzhauer, Jennings then went on to breezily answer the following clue: “This German developed calculus independent of another wise guy” (Gottfried Wilhelm Liebnitz, of course). 

“It works!” Jennings said of Holzhauer’s “all-in” gesture. Holzhauer looked on with approval.

That’s just one example of how the contestants somehow managed to be witty even under a great deal of pressure. 

And Jennings’ changed mindset the night before the tournament, choosing to enjoy the tournament rather than stress about it, played a key role in that.

“It helped me play a lot looser,” he said. “But also it was just a blast out there. I think that’s why you could see us joking around a bit. We were really having fun.” 

Playing smart

But don’t let Jennings’ cool demeanor fool you; he was still terrified to make those large, “all-in” bets. 

“(James) would take players out of the game before the first commercial break by running up big leads,” Jennings said. “The hard part was the big wagers — it’s disturbing honestly to have to wager $60,000 on a single trivia question, even if you know in your heart that it’s strategically right. It’s a lot of pressure to put on yourself. I just happened to get some breaks.”

Throughout the tournament, Jennings landed on eight Daily Doubles. He got seven of them right. Of the 192 questions he buzzed in on, he answered 179 correctly, according to the Seattle Times. That’s a 93.23% accuracy rate.

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Ken Jennings goes “all-in” during a “Jeopardy! The Greatest of All Time” match. Jennings recently spoke with the Deseret News about the tournament.

ABC

But what would end up being one of Jennings’ best moments came near the end of the tournament, when, trailing Holzhauer, he opted to bet nothing during the Final Jeopardy question that asked for the nontitle character with the most speeches in a Shakespeare tragedy. 

That conservative move, he said, all came down to math. 

“In Final Jeopardy, if the game is kind of close, the right move from first place is usually to make a pretty big wager. The right move from second place is almost always to make a smallish wager,” Jennings said. “The only way you’re going to win from second place is if the leader gets it wrong. … If you make a small bet … you can get it right, you can get it wrong. You just doubled your chances of winning.”

Jennings came up with the correct answer — the villainous Iago — and added nothing to his name. 

All eyes shifted to Holzhauer.

“Who is Horatio?” the contestant had written. Holzhauer lost all of his 44,000 points. 

And that’s how Jennings’ decision to wager $0 led to a $1 million victory. 

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Ken Jennings and James Holzhauer shake hands after a “Jeopardy! The Greatest of All Time” match. Jennings recently spoke with the Deseret News about the tournament, which aired in January.

ABC

It was a calculated move, but Jennings was visibly shocked by the outcome. Holzhauer and Rutter — who each went home with $250,000 — lifted Jennings high up on their shoulders so he could hoist his “Greatest of All Time” trophy in the air.

‘It’s still Alex’

But for Jennings, the greatest honor of all was getting to play with his fellow “Jeopardy!” legends — and doing it in front of Trebek, who last year was diagnosed with stage 4 pancreatic cancer

“It was a pleasure to see him again and to see that he was really doing well,” Jennings said. “He’s had his good days and bad days because he was in chemo at the time, but he was really enjoying himself during that tournament.” 

In terms of ratings, the prime-time tournament — which “Jeopardy!” recently announced will be rebroadcast May 4-15 — ended up being a giant. Nearly 15 million viewers tuned in for each episode, putting it on a level with the 2019 NBA finals and the 2019 World Series.

That was satisfying for the 45-year-old Jennings, who as a kid ran home from school to watch “Jeopardy!” every day.

“I could not have been happier when I saw those ratings,” Jennings said. “‘Jeopardy!’ and ABC were blown away by those numbers. I love that the show is such a stalwart. Tonight’s episode of ‘Jeopardy!’ almost down to the second will be the same as an episode of ‘Jeopardy!’ from 1995 or 1985. They got it right the first time. And there’s just not a lot that’s like that in our culture, that never dumbed down or sped up. 

“It’s still ‘Jeopardy!’ And it’s still Alex, thank goodness.”

Late “Jeopardy!” host Alex Trebek is pictured with Ken Jennings.

During his initial run on “Jeopardy!” Ken Jennings amassed more than $2.5 million over a 74-game winning streak. Jennings spoke with the Deseret News about his recent run on the show during the “Greatest of All Time” tournament.

Associated Press

But as Jennings has now claimed legendary status during two different “Jeopardy!” eras, the longtime speculation among fans has again picked up steam: Could Jennings one day be the host of “Jeopardy!”? 

“I mean, it’s absolutely a dream job,” Jennings said with a laugh. “What a great job. … But I really can’t even think about anybody but (Trebek) hosting the show. He’s a hero to America’s nerds. I’m not emotionally prepared for turning on the TV and seeing anybody who’s not Alex Trebek — whether it’s me or not — hosting ‘Jeopardy!’ I’m just not ready to consider that yet.

“I hope he hosts for 100 years.”