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This Man Just Won the First-Ever ‘Jeopardy! The Greatest of All Time’ Tournament

Who is Ken Jennings?

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My grandmother is in her 90s. She moves slowly. She repeats herself. She doesn’t always remember when her beloved Raptors are playing. One thing she does remember: If it’s a weekday, Jeopardy! will be on television.

For the past week or so, my grandmother wasn’t the only one who made sure to tune in when the trivia show started its broadcast. Jeopardy! The Greatest of All Time, which pitted the show’s three most famous competitors against each other in a multinight, prime-time matchup that would award the winner a million-dollar prize, was wildly popular, drawing over 15 million viewers a night, about a 50 percent jump from the show’s usual audience. The tournament also managed to outdo some of the biggest non-football games in American sports. Revenge of the nerds, indeed.

James Holzhauer, Ken Jennings, and Brad Rutter faced off in a series of double-length matches, and at the end of each night, whoever had the most points was awarded a win. The first to three wins would get a trophy and the big prize; the other two would take home a quarter million each.

All three contestants had slightly different claims to fame. Rutter, who made his original run on the show in 2001—when repeat winners could only win five consecutive games before being sent home—participated in five Jeopardy! tournaments, all of which he won. That made him the highest earner in the show’s history. Jennings is the show’s first contestant-turned-celebrity; he still holds the record for the show’s longest winning streak, which he set at 74 games in 2004 after the five-win cap was removed. Holzhauer was pitched as the contestant who had broken the most Jeopardy! records, although it might be more accurate to justify his GOAT inclusion on the grounds of being the “most viral.” Holzhauer, a professional gambler, became a semi-famous figure in the summer of 2019 when his analytics-driven approach to the game allowed him to effectively hunt down Daily Doubles, where he would then make massive wagers and then blow away the competition. Prior to Holzhauer’s first appearance, no player in Jeopardy! history had made more than $100,000 in a single game; during his 32-game win streak in regular play, Holzhauer broke the mark six times. At the end of the year, he won the show’s Tournament of Champions. Call him the Astros of—oh, wait. No, don’t do that.

The tournament felt like something of a last hurrah for Alex Trebek, who has hosted the show for 36 years and was diagnosed with stage 4 pancreatic cancer last March. Despite the stakes, Trebek and the contestants seemed to be at ease, bantering with each other and doing impressions while answering clues. The tournament felt warm, like a reunion; Trebek’s usual instinct to lightly enjoy humor at the contestants’ expense was mostly gone. Rutter’s answer in the last night’s final Final Jeopardy was “You’re the best, Alex.”

Speaking of Brad—how can I say this nicely?—he was not doing the best at this. He spent a troubling amount of time with negative points, finished multiple nights with a zero-point total, and botched seemingly every one of his Daily Doubles while making Holzhauerian wagers. This was the final score of Match 1, and things only got worse from here:

Also, this happened at the halfway point of Match 4:

In the end, though, Rutter and Holzhauer both left the tournament with the same winnings. Holzhauer was within striking distance for nearly the entirety of every night, but he came up 200 points short in the opener and then missed a Final Jeopardy clue at the end of Match 4 that would have given him a win. Jennings won in a tight-but-decisive gentleman’s sweep, only ceding Match 2 to Holzhauer.

Holzhauer and Jennings seemed to be nipping at each other’s heels for most of the tournament, wincing after they lost the buzzer battle on a clue they could answer. Jennings told my colleague Claire McNear that he didn’t think that age would hurt his buzzer speed—ringing in at the right time is a surprisingly important ingredient for success—and it didn’t. He’s the greatest of all time now, until there’s a new tournament with even higher stakes.

I wouldn’t complain about such an event. High-visibility Jeopardy! is fun. Trivia is universal. Knowing things is fun, and perhaps knowing what you don’t know is even more fun. Watching three people know everything (except the name of Bruce Lee’s style of martial arts) while giving each other a hard time is a pastime like no other.