'Jeopardy!' legend Ken Jennings says it's 'inevitable' he will face-off against James Holzhauer

The "Jeopardy!" legend shares advice for the man who nearly broke his record.

ByCatherine Thorbecke, Cameron Harrison, and Alyssa Ponce via via logo
June 06, 2019, 7:25 AM

What is "inevitable?"

"Jeopardy!" legend Ken Jennings selected that response when asked if he would ever face off against the recently-unseated champ James Holzhauer, whose winning streak made headlines before coming to an end just shy of breaking the regular season prize money record earlier this week.

"It's got to be inevitable," Jennings, 45, said in an exclusive interview with "Good Morning America" when asked if there would ever be a Jennings-Holzhauer showdown on the beloved game show.

"But 'Jeopardy!' only does those special tournaments so often," he added. "And obviously I can't get 29-year-old Ken to show up with his sleek, 29-year-old brain, it's got to be me with my broke down brain."

PHOTO: "Jeopardy!" legend Ken Jennings opens up in an interview with "GMA."
"Jeopardy!" legend Ken Jennings opens up in an interview with "GMA."
ABC News

Jennings, of Seattle, holds the "Jeopardy!" record for the most consecutive games won -- 74 -- and the highest winnings in regular season play -- $2,520,700 -- according to the show's Hall of Fame.

Jennings said he was cheering for Holzhauer during his 32-week winning streak, saying, "For many years I have assumed that the record is beatable."

"It seemed like he might be the guy, the chosen one, so I was very excited," he said. "I wanted to see it come down to the wire, I wanted to see if it could be beaten because I think it can be done."

"He was so close to the cash record," Jennings added. "And it just shows how fragile a 'Jeopardy!' streak is."

Jennings even equated Holzhauer's "Jeopardy!" prowess to the AI-powered IBM supercomputer Watson, who famously beat Jennings during a "Jeopardy!" match in 2011.

"Watching James on that show, he feels as close to Watson as you can get and still have a pulse," he said. "My guess is playing against James is going to be a lot like playing against Watson."

While he was rooting for Holzhauer, Jennings said he did grapple a little bit with losing his identity of the instantly-recognizable so-called "Jeopardy Guy."

"It hit me all at once, I'm not that 'Jeopardy guy' anymore," Jennings said. "He's that 'Jeopardy guy,' I'm like your dad's 'Jeopardy guy.'"

Jennings also opened up about his recent set visit to see his old friend Alex Trebek, shortly after he publicly announced his cancer diagnosis.

"I think in recent months he had been doing the show in some pain from his cancer treatments but that day he was in good spirits," Jennings recalled. "That day as soon as the cameras turn on he can turn it on and he can turn into Alex Trebek, that really means a lot to America."

PHOTO: "Jeopardy" host Alex Trebek poses with contestant Ken Jennings after Jennings' record breaking streak on the game show surpassed 1 million dollars, July 14, 2004 in Culver City, Calif.
"Jeopardy" host Alex Trebek poses with contestant Ken Jennings after Jennings' record breaking streak on the game show surpassed 1 million dollars, July 14, 2004 in Culver City, Calif.
Jeopardy Productions via Getty Images, FILE

At the time Jennings competed on the show at the age of 29, he said he was "having this early mid-life crisis."

"And luckily, instead of doing law school or something awful like that, I went on a game show and it was my favorite show," he said. "And it changed my life."

Growing up in a military family in South Korea, Jennings said he watched "Jeopardy!" every day as a kid, on the only English-language TV station he had access to.

"Me and all my friends were just obsessive 'Jeopardy!' nerds from 4th grade on," he said. "It is still the great honor of my life that I got to be on my favorite show, it was a dream come true."

PHOTO: Ken Jennings poses in this undated handout photo from "Jeopardy."
Ken Jennings poses in this undated handout photo from "Jeopardy."
Jeopardy Productions via Getty Images, FILE

While his life changed a lot since winning the $2.5 million dollars, in that he gets to spend more time at home with his children, he says he still "drove the same Toyota Corolla for 10 years" even after winning.

Jenning's advice for young people, and for Holzhauer

Jennings said he has "traded emails" and advice with Holzhauer, who was just a few hundred thousand dollars away from beating his record before his streak came to an end.

"I just told him like take some time to think about what it is you want, because you do have a window, like do you want a different job, do you have a book idea, do you have a podcast idea?" Jenning said of the advice he gave. "Because make some phone calls, now is the time."

Jennings said he would encourage young people who feel like they are different to "follow your obsessions" and "wear those on your sleeves," adding, "that's where your life is going to take you."

"You don't always feel like you fit in as the smart kid, you become aware at a certain age that it's not a hit with girls to know Captain Kirk's middle name," he said. "So I would kind of hide that know-it-all part of myself."

"I love that there is less of stigma now against being any kind of a nerd or a geek," he added. "It's OK to let your freak flag fly."

Finally, Jennings said his biggest advice to Holzhauer would be simply: "Try not to change."

"You hear stories about what any lifestyle change or any windfall can do to people, it's not always great when somebody gets a lottery ticket," he said. "I worked very hard at not doing anything dumb."

"I really feel like James has that down," he added. "He's got his priorities right and his head screwed on great."

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