New ‘Jeopardy!’ Champ Almost Competed Against Ken Jennings During Historic Run

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There’s a new Jeopardy! champ in Season 41, but he nearly played in Season 20! Will Weiss revealed during his post-round interview in the Tuesday, September 10 episode that he originally qualified to compete in the same season of Jeopardy! during which now host Ken Jennings made his historic run.

Jennings won 74 consecutive games from June to November 2004, winning over $2 million in the process. Jennings still holds the record for the most consecutive wins in a regular season of game play. Weiss, a technical program manager from Islip, New York, secured his first-ever Jeopardy win 20 years after he first became eligible to compete, but he never got the call to play back in 2004.

“Were you waiting for that call, or were you hoping to not get that call?” Jennings asked. It’s a fair question. Everyone plays to win this beloved trivia game, and the odds of winning against Jennings are historically slim. Weiss said he would have happily taken on the challenge of playing against the greatest.

“I like to think that I would have been competitive, but I don’t know that I would have appreciated the experience the way that I do now just being older,” he admitted to Jennings, who joked in response, “Plus, now you don’t hate me so much!” As Weiss assured, “I never hated you, Ken. It was a healthy and just ‘whoa’-level respect.”

Competing against Weiss was Mary Catherine French, a writer, editor, and research assistant from Philadelphia, Pennsylvania, and returning champ Adam Reiffen, a Naval officer from San Diego, California, who each had memorable personal stories to share with the audience as well.

French told Jennings and the crowd about squirrels who interrupted her family’s Jeopardy viewing one time, having got in while her house was undergoing a renovation. And Reiffen shared a story about the time his wife snagged tickets for the FIFA Women’s World Cup final in 2019 in Lyon, France, not far from where she was stationed at the time. The U.S. team won against The Netherlands that year.

Weiss may not have gotten to play against Jennings, but his Jeopardy journey did come full circle now that he’s gotten to play with Jennings as host. Weiss won the game with a final score of $14,000. Reiffen ended with $3,999, and French ended with $1,600.

Jennings capped things off with a compliment for the winner: “It’s looking like I’m lucky not to have played you back in 2004!”

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