Ken Jennings, Brad Rutter, and What It's Like to Be the Best Ever on 'Jeopardy!'

If you're looking for the best Jeopardy! players on earth, the Battle of the Decades tournament is a good place to start. But none loom larger than two: Brad Rutter and Ken Jennings. They are, simply, Jeopardy! titans. And they meet Thursday for the third time.

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If you're looking for the best Jeopardy! players on earth, the Battle of the Decades tournament is a good place to start. But none loom larger than two: Brad Rutter and Ken Jennings. They are, simply, Jeopardy! titans. They meet Thursday once again, and whoever wins this third battle (if one wins) will be, indisputably, the greatest of all time.

The Decades tournament is something of a coming home for the top Jeopardy! champions of the past 30 years. There is Chuck Forrest, who kicked off the whole game-theory strategy, and there's Roger Craig, who finds himself in the Decades finals with Jennings and Rutter, and whose bold wagering made him a bit of a viral star a few years back. The former champions are chummy, they hang out off-stage. "It’s definitely an insider club ... sort of like a weird fraternity," Rutter told The Wire in a phone interview. Jennings, also in a phone interview, described it as "this sort of weird Band of Brothers thing ... if the Band of Brothers guys then had to go shoot at each other on the battlefield." But when it comes to Jeopardy!, it's Brad and Ken, and everybody else.

Brad Rutter has won a grand total of $3,385,702 on Jeopardy!, the most ever. He's never officially been beaten by a human opponent. The one time Jennings bested him was during the IBM Challenge versus Watson, when Jennings came in second and Rutter in third. But Jeopardy! counts that as an exhibition match, so Rutter's official slate remains clean. In his first match against Jennings, Rutter nearly doubled him, $62,000 to $34,599. He's the best ever, money-wise, and he plays like it: there's a slick confidence to his gameplay. During his contestant interview in the semifinals, Brad mentioned buying a Porsche with his winnings; he finds amusement in retweeting his "haters" as his episodes air.

Ken Jennings won the most Jeopardy! matches ever in a row – 74, a DiMaggio-esque unbeatable mark – and has earned $3,196,300. He is, arguably, the most famous of all Jeopardy! contestants; five books, a board game, and a slew of media appearances followed his streak. Most conversations about Jeopardy! players begin and end with him. Jennings plays like the boy-genius-next-door, youthful and affable, like the kid who just can't help but raising his hand in class.

Courtesy Jeopardy Productions, Inc.

Together, they're Jeopardy! royalty. "In the Jeopardy! green room there are now two checks, there are big fake checks on the wall, with my total winnings and Brad’s total winnings," Jennings said. "You see that every time you go back stage on Jeopardy!."

When they face each other Thursday for the third time, they'll have a history that is exceptionally rare for a show like Jeopardy!. "Before [Ken and I] were getting on stage in the finals we were joking to [Roger Craig] that, 'Hey, we’re still auditioning for a third here. Jerome [Vered] didn’t quite work out, Watson’s a dick, so we can make this a thing,'" Rutter said.

As much as a game show can have a rivalry, Rutter versus Jennings is Jeopardy!'s. Well, on-stage at least.

"I think Jeopardy! would like it if there were some easier to construct narrative where one of kicks babies or something, or if we really hated each other, that would actually probably be good for them, but sadly we don’t," Jennings said. Indeed, he and Rutter are good friends off-stage. They're the only two people on earth to understand what it's like to command their unique sort of Jeopardy!-celebrity, after all.

When Jeopardy! first contacted them about the Decades tournament, there was a kind of inevitable "here we go again" feeling. "[Facing Ken again] was definitely in the back of my mind, and I think if you ask most people that’s what they would’ve predicted. But at the same time, you don’t want to get ahead of yourself, there’s a bunch of great players in this tournament," Rutter said. Jennings, too, saw this final coming: "On the one hand, maybe this will finally be the tournament where somebody takes out Brad ahead of time. On the other hand, yeah, another final against Brad," he said.

The Decades tournament serves as a tie-breaker of sorts. If Ken wins, he'll have toppled Brad in official tournament play and overtake him as all-time money leader. If Brad wins, he cements his place as the best ever. Because he played pre-2003, when contestants were limited to five days in a row, Brad never had a chance at a streak like Ken's ("I do remember when Ken was on being a little jealous back in '04, like 'Man I think I’m just as good as this guy and he’s getting all this attention,'" Rutter said). If he beats Ken yet again, though, Brad's dominance would be undeniable.

With the friendly relationship they have off-stage, that leaves an awkward tension: "When we’re hanging out, we’re both Jeopardy! players with a lot in common so we can bond on that level, and I’m just trying to ignore the fact that at some point we’re just going to have to go up on stage and try to massacre each other,” Jennings described.

Their dominance is felt among their fellow contestants, too. Even their competition in the tournament, all former champions themselves, looked to Brad and Ken as the ones to beat. "I certainly felt like there was a little more pressure on us, we’re the ones that are expected to win," Jennings said. "And also people just not wanting to play [Brad and I], people getting bummed when they would read out the seedings. I was surprised, I sort of thought at that high of a level, it’s really anybody’s game any time, but it seemed like it was definitely perceived that there were some top elite there."

Courtesy Jeopardy Productions, Inc.

The Brad vs. Ken final almost didn't happen. In Jennings' semifinal match, he bet big on a Daily Double and lost it, and eventually ceded his once-runaway lead to Forrest, before getting it back in the final minute of play. "You’re not panicky, because it really is just going too fast, but you are just frantically treading water trying to keep up," Jennings said. "I never really felt like 'I’m going to lose the game' but I did feel like it was a little more stressful."

According to him and Rutter, it's all about momentum, and the buzzer. "The buzzer timing is so important and when you get into a rhythm like that – to go back to baseball you’ll hear hitters on a hot streak say that the ball looks like a beach ball –and when you have the timing on the buzzer and you’re just getting in whenever you want, that seems to sort of snowball," Rutter explained.

That's what makes the two of them very nearly impossible to beat – they are so often the ones seeing the beach ball. They rush out of the gate, scooping up every clue, and leave their opponents floundering. There's an intimidation factor inherent in matching up against Jennings or Rutter, and it only piles on in-game. "You hardly ever see that," Jennings said of Forrest's brief comeback. "Usually people who are down $10,000 early, you can just see them check out." That's what happens with most people Jennings and Rutter play, that's why at the end of the day, they're "the only two people who could put 'Occupation: Jeopardy! Contestant' on our tax returns," as Jennings put it.

But regardless of outcome, whether Jennings or Rutter are victorious or Roger Craig becomes a new Jeopardy! legend this week, a giant slayer, they're just enjoying themselves, thankful to be back. It's a game, you know.

"Not that I didn’t have fun at the others, but I think I had a lot more fun this time," Rutter said of the Decades tournament.

Jennings echoed: "You don’t get to do it often enough, and you just try to enjoy it when it happens."

This article is from the archive of our partner The Wire.