Will James Holzhauer Win The ‘Jeopardy!’ Greatest Of All Time Tournament?

In 2019, James Holzhauer broke ‘Jeopardy!’ but 2020 could be the year he officially becomes the greatest player in the show’s history. He’ll get his chance on Tuesday night, when the Jeopardy! Greatest Of All Time Tournament starts on ABC. The contest pits Holzhauer, winner of more than $2.4 million and last fall’s Tournament of Champions, against two other all-time contestants, Ken Jennings and Brad Rutter.

Here’s a preview of what to expect during the multi-night prime time event, as it’s a bit different from the regular syndicated Jeopardy! you’ve come to know and love.

What’s the Jeopardy! GOAT Tournament?

Basically, the makers of Jeopardy! saw the attention James Holzhauer’s record-smashing run garnered last year and decided to settle, once and for all, who the best player in Jeopardy! history is. They asked Holzhauer to play against Ken Jennings and Brad Rutter, two hugely successful contestants from the not-too-distant Jeopardy! past to play a unique tournament, with the winner taking home $1 million and the runners up netting a cool $250,000.

The tournament starts on Tuesday night on ABC at 8 p.m. EST, so don’t expect to see this in whatever time slot and channel your ordinary Jeopardy! episodes usually air. This is the first time Jeopardy! has held a true prime time event in a few decades, so your confusion here is absolutely reasonable. And that points to just how unique an event this is.

The format itself is different from other Jeopardy! games as well. We already have a finalist group, after all, so there’s no need for all the buildup. Instead, the potential GOATs will play a first-to-three format that will span an unknown amount of nights on ABC. We could see up to seven games between the three contestants, though the first one to three wins will take the crown.

Each night is an hour-long contest that will feature two full Jeopardy! games, with the night’s total scoring determining the winner. Basically, it’s a tournament final each night, with a winner determined at the end of each hour. First to three total wins takes the crown. This sets up some extremely dramatic potential for Final Jeopardy wagering and results, which is just one of the many reasons trivia nerds are amped up about this. But who are these guys, anyway?

Who is James Holzhauer?

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If you’re asking yourself this question, well, I’ll be honest I’m fairly surprised you are here.

Still, it’s a good question! Jeopardy James, as he’s jokingly called himself, is a professional sports bettor from Las Vegas, Nevada who burst onto the trivia scene in 2019 by dominating Jeopardy! and smashing nearly every single-day win total in the process. Holzhauer won more than $2.4 million with huge paydays that set the internet ablaze and made syndicated television appointment viewing for a very small sliver of Reddit.

He did well on The Chase back in the day, sure, but Jeopardy! was a lifelong obsession for Holzhauer and he did his damn homework before he showed up. He likes the Las Vegas Golden Knights, the Chicago Cubs, and completely embarrassing his opponents on the Jeopardy! stage to the point where games are no longer competitive by the first commercial break.

Holzhauer has an unorthodox game style that drives cluemakers nuts but is extremely effective, quickly answering high-money questions correctly to build a cash pot and then hunting for Daily Doubles, which he uses to wager all of his money on and effectively double his score. It works really well because 1) he knows game theory and 2) also all of the answers and rarely makes mistakes. He’s not invincible, as Emma Boettcher showed when she ended his 32-game winning streak last year. But he’s an extremely exciting opponent to watch, and his strategy works against experienced players, as he proved by winning the 2019 Tournament of Champions in November.

James is also extremely funny on Twitter, and he’s been tossing some playful shade at Ken Jennings for the better part of a year now.

Who is Ken Jennings?

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Jennings is the first Jeopardy! player that many said broke the game, winning 74 straight episodes over the course of two seasons in 2004, brilliantly navigating through weeks of grueling 5-episodes a day tapings. He was the first person to win on the show so long his episodes were actually airing on TV while he was flying back to Los Angeles to tape more wins. Contestants knew they were dead in the water when he showed up in the parking lot, and for a while there wasn’t a bigger name in trivia.

He parlayed his Jeopardy! stardom into writing books, appearing on podcasts and generally doubling down as a trivia kingpin in a variety of ways. He has a very good trivia newsletter and is still, most likely, the most recognizable person in this tournament other than Alex Trebek. He’s appeared in a number of other Jeopardy! tournaments in the years since his initial run, always running into the final competitor in this tournament.

Who is Brad Rutter?

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Perhaps the most valid question of the bunch considering you’ve likely listened to a podcast with Jennings on it and Holzhauer is the freshest face of the bunch. I’ve seen a lot of “that poor other guy” sentiment when it comes to Rutter’s presence in the GOAT Tournament, but he’s arguably the most accomplished of the trio when it comes to both prize money and big time performances against tough competition.

Newer Jeopardy! fans might not know Rutter because he first played at a time when contestants could only win five games in a row. He did, and went on to dominate a number of tournaments later in his Jeopardy! career. Many feel he’s the greatest player ever and would have gone on a long run of wins if he were given the chance, but we’ll never know what could have been if the rules were different back in 2000.

Rutter’s main claim to fame is that in 21 appearances on some form of Jeopardy!, he’s never lost to a human being. He won $55,102 during his first 5-day run, then won the 2001 Tournament of Champions for another $100,000 prize. In 2002, he won the Million Dollar Masters Tournament, taking home a $1 million prize to make him the most monied Jeopardy! champion of all-time. Rutter added to that in 2005 for the Ultimate Tournament of Champions, winning that as well and another $2.1 million.

He added to it in the 2014 Battle of the Decades tournament, besting 30 years of Jeopardy! players and winning another million dollars at the expense of players including Jennings. A 2019 All-Star Games tournament saw Rutter win again, and as team captain he led two other players in a series of team sports and cooperative games. Just kidding, they played Jeopardy! and split another million dollars.

The point is that Rutter has won a lot of Jeopardy! games against top competition since 2001, winning a ton of money in the process. He’s extremely good at this, though he’s never gone on a long run of wins broadcast over the course of weeks like Holzhauer and Jennings. Perhaps more importantly, he seems to have Jennings’ number at this point, beating him in tournaments a few times in different formats. He and Jennings also appeared together in the 2011 Jeopardy! IBM Challenge, where an artificial intelligence named Watson ended human dominance of the trivia world, but Watson can’t spend money and will never know love.

Who will win?

This is a great question, though apparently someone in Las Vegas already knows the result. The presumptive favorite is Holzhauer, who has played the actual game most recently and has a strategy that’s proven to work against top talent. Jennings has said in a number of ways that Jeopardy! is a young man’s game, and Holzhauer is certainly the youngest of the bunch.

If you’re looking for a prediction, it certainly feels like this is Holzhauer’s tournament to lose, as unfair as that sounds. He’s played a lot of Jeopardy! over the past year, which means a lot of reps with the signalling device and hearing the cadence of Alex Trebek’s voice. In these kind of matchups it’s not whether you know the answer — all three players are clearly great at trivia — but whether you can ring in first. Jennings admitted he’s been practicing with a fake buzzer at home, as Rutter and Holzhauer assuredly have done to prepare as well, but there’s no substitute for the real thing and Holzhauer has proven to be extremely good at his timing.

That said, Jennings has pointed out that he’s never beaten Rutter, who Holzhauer has never had to play, either. Alex Trebek, meanwhile, says Holzhauer is the favorite for all of the reasons listed above. Basically, everyone is picking everyone else, which makes for a fair bit of drama and gamesmanship. It should be fun.


It should be noted that there are a LOT of ways the results could be spoiled, so be careful out there if you’re looking to avoid knowing what happens before it actually airs in your market. The full tournament was taped in mid-December, so it’s possible the full results leak out and someone jumps the gun. We’ll have posts recapping the day’s events shortly after it airs, but the rest of the internet follows its own rules, so be careful.