‘Jeopardy!’: Ken Jennings’ 1 Major Mistake on the Show Could Have Landed Him in Jail

Ken Jennings is arguably the most well-known contestant to ever appear on Jeopardy!, and he’s certainly left a legacy. But the popular game show contestant once nearly got himself in deep trouble on the show — with a move that could have resulted in jail time.

Ken Jennings holds the longest-ever ‘Jeopardy’ streak

Only a few years before Jennings’ time on the show, the Jeopardy! rules were different from how they are now. Up until 2003, contestants were only allowed to appear on five consecutive episodes. If they defeated their opponents in all five, they were invited back for the Tournament of Champions but could no longer appear on the show.

Eventually, though, the show canceled that rule and decided that winners could appear as many times in a row as they could win. For Jennings, whose streak started in June 2004, this was the best case scenario. Between June and November 2004, Jennings won 74 straight games. On November 30, Jennings lost to Nancy Zerg, ending his streak but effectively marking him as the greatest contestant of all time.

Jennings had to work hard to make sure his streak stayed a secret

As Jennings continued to win, it became more and more difficult for him to conceal it. Shows are often taped several months in advance, so Jennings had to constantly remain mysterious about whether his streak would continue into the following day. According to Brain Sharper, Jennings’ boss had to cover for him while he was filming so as to not give away that he was still on the show. Jeopardy! filmed on alternating Tuesdays and Wednesdays, and Jennings’ boss continually came up with excuses for why he wasn’t in the office.

Jennings made a mistake that could have sent him to jail

Surprisingly, Jennings nearly landed himself in serious trouble as a contestant. While filming, producers asked Jennings to change his tie, but they reportedly sent him backstage on his own. While there, Jennings came dangerously close to entering the room where the Jeopardy! answers were kept, according to Brain Sharper, which did not go over well with producers. Though it was an honest mistake, Jennings could have gone to jail for cheating during the game show. Thankfully, it was understood that it wasn’t his intention (and he never actually saw any answers).

No ‘Jeopardy’ contestant has come close to Jennings’ streak

These days, Jennings is still known as the greatest Jeopardy! player of all time. And nobody has ever come close to surpassing his streak. James Holzhauer, who appeared on the show in 2019, nearly edged out Jennings in the most earnings (but was still behind), though his number of appearances never came close. Holzhauer appeared fewer than half the number of times as Jennings, only appearing in 32 games to Jennings’ 74.

Jennings won more than $2.5 million during his appearances, while Holzhauer took home just over $2.4 million. Though Holzhauer had much higher average winnings per game, he couldn’t quite beat Jennings’ record.