Like that kid who grew up incessantly dribbling a basketball or lobbing a baseball high in the air to practice shagging flies, Ken Jennings had big dreams.

It wasn’t buzzer beaters he daydreamed about, though ironically buzzers would end up having a lot to do with his success. No, Jennings dreamed a smart kid’s dream, to one day whip all comers with his brain in a contest of wits.

As the Seattle resident prepared for this week’s “Jeopardy! The Greatest of All Time” tournament, it’s not hyperbole to say he felt a little like Michael Jordan heading into the biggest game of his life.


“If you had told 5-year-old me that you’re going to be famous for being on a game show, I would have been so happy,” said Jennings. “I was a 5-year-old ‘Family Feud’ and ‘Pyramid and ‘Tic-Tac-Dough’ addict and it really is a dream come true. And not just any game show, but my favorite one: ‘Jeopardy!’ So it’s all just been surreal really. Like, I hope I don’t wake up, right?”

Jennings will take on exciting newcomer James Holzhauer and longtime rival Brad Rutter in the tournament that kicks off at 8 p.m. Tuesday on ABC. The first contestant to win three matches earns the title of “Greatest of All Time,” and it is very much like Jordan, the Chicago Bulls great, squaring off against LeBron James and Magic Johnson in a game of H-O-R-S-E to finally settle the question of who’s the best.

Like that endless, swirling debate over the NBA’s all-time best basketball player, this week’s shows offer a fascinating look at the most accomplished players to ever play “Jeopardy!” in the show’s 39 years. If there was a Mount Rushmore of “Jeopardy!”, Jennings, Holzhauer and Rutter would have their profiles carved into the mountain alongside longtime host Alex Trebek.


“ ‘Jeopardy!’ is usually one to a customer,” Jennings said. “But every two or three years the phone rings and I’ve been invited back. I’ve heard Alex say that for a very small number of people, ‘Jeopardy!’ is not a game show, It’s an annuity. And it’s certainly true. It was always my favorite show. So playing is so fun that it’s really just a great honor and joy to me that occasionally I get to go back on and see if I still have it, basically.”

This will likely be the steepest challenge of Jennings’ game-show career. There’s $1 million on the line to the winner, with the runners-up earning $250,000 each, further padding lucrative runs for the trio of trivia overachievers. Like the debate between basketball’s best players, each has shown different, hard-to-compare strengths over the years.

While waiting to catch a plane to New York for a promotional appearance, Jennings took time this weekend to break down the field. Here’s his take on each of his opponents.

Jennings’ Scouting Report on Brad Rutter

Rutter, a 41-year-old aspiring actor now living in Los Angeles, played the game back when the rules ended a champion’s run at five consecutive wins. But he has cleaned up over the years in multiple tournaments to become the show’s top money earner at more than $4.6 million, making him the highest earning American game-show contestant of all time.

Rutter has never lost to a human in the game. He was beaten by IBM’s Watson computer and Jennings in a 2011 match that’s considered an exhibition. And he has trailed on Day 1 of a couple of two-day tournaments, if you’re splitting hairs.

“He’s like Rocky Marciano,” Jennings said. “He’s undefeated and it’s because he really brings it on game day. I’ve watched him sitting in the crowd, I’ve watched him at the next podium, I’ve watched him on TV, and he just always finds a way to win. If he’s down early, he keeps a cool head and gets a daily double when he needs to. If he doesn’t know a final ‘Jeopardy!’ answer, you can see him sit for the whole 30 seconds and tease it out and, you know, come in with it at the last second. He’s the Seahawks, a second-half team. He will always find a way to beat you.”


Jennings’ Scouting Report on James Holzhauer

Some longtime watchers think “Jeopardy! James” broke the game during his impressive string of 32-straight wins. Known for his aggressive approach, statistics-based strategy and seemingly endless knowledge, the 35-year-old Las Vegas sports gambler used uncommon flair to become arguably the game’s most popular player.

Jennings has watched him closely and says Holzhauer’s put an incredible amount of thought into every aspect of the game.

“He’s trained extensively on the physical aspect of [ringing in],” Jennings said. “You know, what can he do to get his reaction down from 0.2 seconds to 0.18 seconds or whatever. There’s a specific amount of caffeine he likes to have. There’s a way he likes to hold his arm. It’s why he refuses to wear a suit coat. It’s why he wears those V-necks, because he wants to have a certain kind of flexibility. So he’s tested all this extensively. It’s like he’s done a NASA experiment to beat me at ‘Jeopardy!,’ which is fantastic.”

Jennings’ Scouting Report on Jennings

The 45-year-old author of 12 books comes with his own measurables, and they’re impressive. He holds the record for the show’s longest winning streak at 74 straight games, a seemingly endless run that drew national headlines. And he’s won more than $3.3 million, including tournaments.

Like Holzhauer, he has worked hard to improve gaps in his knowledge and perfect his buzzer routine. Like Mike and LeBron and all the other greats, though, he’s finding that time, and not the field, may be his biggest foe.

“I have to say, especially in the last 10 years and into my 40s, I have found that I have lost a step, maybe not unlike Tom Brady,” Jennings said. “The recall is just not as good. It used to be automatic. Like if I heard something that I was interested in, it was just in there forever. And now I find that if I haven’t thought of a name in a few months, it’s going to take me a few seconds. And sometimes Alex does not give you a few seconds.”


“Jeopardy! The Greatest of All Time” premiers Tuesday, Jan. 7, on ABC, at 8 p.m. PT.