Ken Jennings Reveals Why He Thought He'd Lose 'Jeopardy!' GOAT Tournament, Gives Update on Alex Trebek (Exclusive)

Ken Jennings won the Jeopardy! Greatest of All-Time tournament earlier this year by defeating former Jeopardy! champs Brad Rutter and James Holzhauer. And while it seemed like Jennings had no problem winning the matchup, he didn't think he had the best chance coming out on top. had a chance to catch up with Jennings, who famously won 74 consecutive Jeopardy! games in 2004, and he explained why the GOAT tournament was challenging.

"When I went on Jeopardy! in 2004, it was a very different game," Jennings said in our PopCulture@Home series. "Players like James and Brad re-invented the game by kind of applying game-theory and gambling theory, making big, scary wagers, tackling different orders of approaching the game board… We didn't have any of that in 2004. This was like the horse and buggy era. There was no way to study old games online. Nowadays you have people building simulators for themselves at home so they can practice getting in Jeopardy! fighting shape."

Jennings' response leads to the question: How did he win? "Really, all I could do is try re-learn James Holzhauer's style of Jeopardy! and hope I caught a few breaks," Jennings stated. "But his style of play is so risky it can really be disastrous if you catch a few bad breaks. Luckily I had better luck than any of the two players in that tournament… A lot of things had to fall just right because there is a lot of luck in the game of Jeopardy. But hey, I will take it."

Jeopardy! The Greatest of All-Time was the first time the game show aired in primetime on network television. Jennings won the grand prize of $1 million and has won a total of over $5 million in game show winnings. Because of Jennings' work on Jeopardy!, he is a consulting producer for the show's 37th season. And the 46-year old gave an update on host Alex Trebek, who is battling pancreatic cancer.


"He was visibly cranky during the hiatus because Jeopardy! had to take a slightly longer than usual hiatus because they ran out of new shows and weren't allowed to tape during the pandemic," Jennings explained. "Alex was climbing the walls. He wanted to be working. He really missed it. I've watched him on that set and it's where he feels his most capable, his most confident, his most old-self despite the cancer battle. That's why he's going to keep doing that job for as long as he can and we are lucky to have him."