Ken Jennings on why 'Jeopardy! Masters' winner James Holzhauer was unstoppable

James Holzhauer is the first “Jeopardy! Masters” tournament winner. And there’s one man who got a front-row seat to the three-week ABC tournament (and can brag that he beat the sports gambler in the Greatest of All Time tournament): Host Ken Jennings.

Holzhauer racked up enough points in Wednesday’s two-game finals to overcome opponents Mattea Roach, who placed second, and Matt Amodio.

The three-week tournament began May 8, and also featured contestants Andrew He (eliminated in the semifinals), Amy Schneider and Sam Buttrey.

“Having firsthand knowledge of how hard it is to beat James at ‘Jeopardy!’ ― he's the only one of the six I've ever played ― I knew he was very tough to beat,” Jennings says in an interview. “I assumed the road to the Trebek Trophy would have to go through James Holzhauer.”

Jennings, who set the record of most consecutive wins (74) in 2004, dishes on his relationship with his "Jeopardy!" nemesis, assesses the Masters winner's strength and reveals why the tournament's final episodes delayed taping. (Edited for length and clarity.)

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Question: Why is James Holzhauer such a strong opponent?

Ken Jennings: He seems to be getting better. He looked as strong in this tournament as I've ever seen him play, even though he was playing the best and the brightest. I have to assume he's doing the work. It's like any other game or sport. Being good at “Jeopardy!” takes training, and I think for James, making himself into the best “Jeopardy!” player he can be is kind of his day job.

How good does it feel knowing that you beat him in the Greatest of All Time tournament in 2020 and you didn't have to play him in Masters?

What really feels good is knowing that now I'm retired and I don't have to play him again. I'm safe over at the host's lectern. But for me, the story of that last game is Mattea Roach having him on the ropes once in the semifinals and once in the finals. It shows that anything can happen out there.

The way you and James Holzhauer tease each other is an entertaining aspect of the show. When did that ribbing start, and what’s behind it?

I actually give James almost 100% of the credit. He's a guy who grew up watching pro wrestling, and bless his heart, he (saw) “Jeopardy!” and thought, “Hey, this should be more that.” During the G.O.A.T. tournament, he would talk a little trash. He wasn't afraid to interrupt Alex if he had a good joke at my expense or Brad (Rutter’s) expense.

At the time I thought, “Hey, come on! Show some respect.” But in hindsight, that was the thing that kind of changed “Jeopardy!” and showed us what the game could be if the players were a little loose and funny and having a good time.

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What is your relationship like off the set, if you have one? Are you friends?

The funny thing is, we were actually pretty good friends. There was a group chat. Now that I host the show, I feel a little bit of a responsibility to have that Trebekian distance, that remove and not to be too chummy with the contestants, because there are still federal laws that regulate game shows and it's not a good look if the host is going out for drinks with the contestants. So I find that I don't get to hang out with “Jeopardy!” contestants as much as I used to. But if you've seen James in a social scenario, it's not a huge loss.

I understand there were delays in completing the taping of the tournament, and that Wednesday’s finale was taped just last week.

There were three delays. Andrew (He's) wife went into labor during a game. Then I got a COVID-positive test that never actually seemed to turn into COVID. I don't think I actually had COVID, but we had to delay a full week. And then, worst of all, Mattea’s dad passed away while they were on set. We were just determined to finish this thing. But that was just unprecedented in the annals of “Jeopardy!” to have that kind of real-life drama going on. We prefer to keep the drama to the Daily Doubles.

The contestants banded together at all those points and said, “Hey, Andrew's wife is in labor. We're not going to play this last game.” Or, “We can't tape tomorrow. We’ve got to send Mattea home to be with their family and bury their dad.” The contestants were absolutely unified and there for one another.

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