The Washington PostDemocracy Dies in Darkness

Ken Jennings talks James Holzhauer ‘feud,’ Brad Rutter’s losses and that brutal Bloomberg tweet

Ken Jennings won the $1 million prize after he defeated James Holzhauer and Brad Rutter during “Jeopardy! The Greatest of All Time” tournament on Jan. 14. (Video: The Washington Post)

Last year, shortly after professional gambler James Holzhauer sent “Jeopardy!” ratings skyrocketing by raking up astonishing amounts of money on the nightly quiz show, producers sent an inquiry to the legendary Ken Jennings: Would he be interested in competing in a “Jeopardy! The Greatest of All Time” tournament with Holzhauer and Brad Rutter, the two other most successful players in history?

Jennings, who became a ­pop culture sensation in 2004 when he dominated with a record-shattering 74-game winning streak, had an immediate response: No thanks.

“I didn’t think I had a chance,” Jennings, 45, said in a phone interview Wednesday with The Washington Post. “I felt like I was a little too old, not really on top of my game like I had been 15 years ago. James is clearly the new hotness.”

Eventually, producers persuaded him. “I think I’m out and then they pull me back in, like a Michael Corleone thing,” Jennings joked. He flew to Los Angeles for the taping in December and told himself there was no pressure and he would just play to have a good time.

As millions of viewers saw Tuesday night, Jennings had a really good time. He won three two-game matches over four nights of hour-long prime-time specials, defeating Holzhauer and Rutter to win the $1 million grand prize. The runners-up each earned $250,000.

“It has taken 15 years for Ken Jennings to finally answer the question: Is he as good as he appeared to be in that great run on ‘Jeopardy!’?” host Alex Trebek asked in the closing minutes of the episode.

Obviously, the answer was yes, even though Jennings is effusively kind about his fellow competitors. Unlike any of his previous games, he knew who the other players would be, and he had watched in awe as Holzhauer steamrolled everyone in sight last spring, aggressively pouncing on the highest-valued clues and wagering everything. Jennings knew he had to play the same way.

Perspective: ‘Jeopardy!’ has named its Greatest of All Time. But why did it have to go there?

“James changed the game so much that . . . [we] had to adopt his strategy to try to contain him because otherwise he was going to run away with the thing,” Jennings said. As a result, Jennings had to make uncharacteristically large wagers, such as in the first game in the final episode, when he bet everything (20,200 points) on a Daily Double. When he answered correctly, it practically sealed his victory, even after Holz­hauer made a comeback in the second game.

But all that admiration for Holz­hauer didn’t stop Jennings from getting into a very entertaining Twitter “feud.” After one loss, Holzhauer wrote, “My wife is going to make me role-play as @KenJennings tonight.” Jennings’s response: “It’s all about timing on the button.”

“I don’t usually have the stomach for those kind of jabs, especially with someone I know, but James is very comfortable with that. He’s a pro-wrestling fan, he likes the taunting and bluster,” Jennings said. “He was egging me on. I’m a nice church boy!”

However, Jennings didn’t hold back on another tweet that went viral on Wednesday. Presidential contender Mike Bloomberg’s Twitter account wrote, “Remember, tonight’s winner goes on to face defending champion Ken Jennings. #DemDebate.” Jennings said that when he saw another Bloomberg ad on TV throughout the broadcasts, he was “rolling his eyes” that the Democratic candidate was spending millions to barely crack the polls instead of using that money to help climate change. So he tweeted back, “Remember, defending champion Ken Jennings wants you to vote for Bernie Sanders or Elizabeth Warren.”

As for poor Rutter, who flailed during each episode and routinely lost everything on Daily Doubles? “He’s the most tenacious ‘Jeopardy!’ player I’ve ever seen,” Jennings said of his friend, who went into this tournament as the highest-earning contestant of all time and beat Jennings multiple times in previous ones. “This time, he never quite found his footing. That makes it hard when playing catch-up, especially against James.”

We talked to Brad Rutter about that ‘Jeopardy!’ tournament to ask: What happened, Brad?

Ever humble, Jennings insists that he wasn’t putting on an act when he appeared visibly relieved after answering a tough question — much of “Jeopardy!” is educated guessing. He emphasized that victories are also about luck: if you can find the Daily Doubles, if you know the toughest clues. (Jennings loved the challenging category on the final night where they had to match Roman numerals to initials, even though it led to his hilarious mix-up of Charles Lindbergh and Courtney Love — “a mistake that very few people have ever made,” he acknowledged.) And, of course, it’s all about the timing on that tricky buzzer.

“The whole approach is based on Alex’s voice and cadence that we’ve all heard so many times, we know exactly how he’s going to read a clue,” Jennings said. In preparation, he watched a ton of “Jeopardy!” and tried to become as familiar as possible with Trebek’s inflections.

Trebek was one of the main reasons Jennings wanted to return to the show, he said, sounding emotional as he talked about reuniting with the iconic host. Trebek recently revealed that he resumed chemotherapy for Stage 4 pancreatic cancer after disclosing his diagnosis last year; Jennings, Holzhauer and Rutter wore purple pins during each episode as a tribute to those fighting pancreatic cancer.

“I knew I would kick myself if I missed the chance to play ‘Jeopardy!’ with Alex one more time,” Jennings said. “He just did a phenomenal job during that tournament.”

Jennings’s first-ever “Jeopardy!” appearance started mildly enough on June 2, 2004, when he won about $37,000. Then he won again. And again. And again. And again. “Jeopardy!” had recently instituted a rule that allowed contestants to win as many games as possible — for its first 19 seasons, players could only win up to five times. And then Jennings kept winning. And winning. And winning.

Breathless news coverage followed that summer when “Jeopardy!” ratings spiked as millions tuned in to see the genial trivia expert stomp all over every contestant who crossed his path. He was dubbed a “cold-blooded game show assassin” who was holding the show “hostage.” When he crossed the $1 million mark, one newspaper called him the “Lance Armstrong of trivia champs.” Jennings joked that his name became so ubiquitous that even his son, who was a toddler at the time, started calling him “Ken Jennings.”

Fifteen years later, his son is the one who drove him to the airport so he could travel to the taping. Jennings said he had such low expectations about actually winning that when he did, he started crying. He can’t see ever returning to the show, especially with a host other than Trebek, and said it was the perfect way to go out.

“It was surreal, I felt like I was in shock,” Jennings said. “Finally, everything went right at the very end of my career. It was an enormous sense of relief that I was going to be able to leave the stage a last time a ‘Jeopardy!’ champion.”