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Former 'Jeopardy' players who competed against Ken Jennings reveal how it went: 'He was a beast...'

In a Reddit thread, fans of the show gathered to share their experience of going up against Jennings.
PUBLISHED MAY 2, 2025
Screenshot showing Ken Jennings on Jeopardy! (Cover image source: YouTube/Jeopardy!)
Screenshot showing Ken Jennings on Jeopardy! (Cover image source: YouTube/Jeopardy!)

Before becoming the friendly host of "Jeopardy!" Ken Jennings was a legend of the game with 74 straight wins, a streak during which he crushed a lot of opponents. One of the questions that fans often have is about the contestants who lost out to Jennings back in those days. The answer to this emerged on a Reddit thread, where people shared their experience of going up against the "Jeopardy! G.O.A.T" in various games.

Screenshot showing Ken Jennings speaking to the hosts of
Screenshot showing Ken Jennings speaking to the hosts of "Inside Jeopardy!" (Image source: YouTube/Inside Jeopardy!)

During his original run in 2004, Jennings faced two different people each night, and by the end of his streak, he had racked up $2,520,700 in winnings for regular gameplay, which is the highest ever, according to the show's website. wondering what happened to the losers, one user asked, “Did anyone here face Ken Jennings? Is there anyone in this sub that went up against Ken Jennings in his original 75-episode run?” @DanielRLonergan18 on the show's unofficial forum. 

While the majority of the Redditors said they never faced Jennings, some said they played against the legend in different games. "I played him in a quiz bowl practice once. He smoked everyone on a tossup on the WWE Intercontinental Title. (I know not what you asked exactly, but I did play him in some form of quizzing, so it’s something!)" user @brosbeforetouhous wrote. 


Comment
byu/DanielRLonergan18 from discussion
inJeopardy

 

There was one user who did go up against him in a promotional event for the show and learned why he was the best player and the best host for the show, too. "Ken came out with a board game called "Can You Beat Ken" back when he finished his original run. I attended a promotional event and we got to play a 3-question game against him one-on-one. There is a reason he was a 74-day champion and I can't pass the test lol. About 20 years later, I brought the game piece with me to Jeopardy Live and was kind enough to sign it for me." @bluegambit875 claimed.


Comment
byu/DanielRLonergan18 from discussion
inJeopardy

 

Turns out, Jennings has a habit of playing quiz games and destroying his competition everywhere. "I actually went up against him in a team Quiz Bowl event at TCONA* (the Trivia Championships of North America) in....either 2012 or 2013. Interestingly enough, one of my teammates (and a friend) was Adam Villani, who had put up a valiant fight against Ken on Game 61 of his run (he would later end up doing quite well on 500 Questions)," @pyralspite74 mentioned. "Ken was a beast - a friendly beast to be sure, but a beast," the user added.


Comment
byu/DanielRLonergan18 from discussion
inJeopardy

 

Meanwhile, there was one Redditor who came close to facing off against Jennings on "Jeopardy!" "I ALMOST did. Taped in September 2004 - I think he lost maybe two weeks before my tape date. His final game aired in late November, mine aired in late December." @Glass-Guess4125 said. 

There was another user who claimed that they knew one of "Ken's Victims." "My roommate at the time went up against him. Said he was a great guy. Would love to see him back as part of a tournament of Ken's victims," @fac429 commented.


Comment
byu/DanielRLonergan18 from discussion
inJeopardy

 

Turns out, "Ken's Victims" is a real thing that existed back when Jennings was at the top. "Back when Sony had a chat room, many former contestants that lost to Ken started identifying themselves as 'Ken Jennings Loser'  by having a number they lost to (for example KJL#14). It was almost like seeing a club meeting in a chat room. I wonder how many are here in Reddit!" @QuaintMelissaK asked. 

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