Greatest of All Time on ‘Jeopardy!’: Who Won Game 1?

The first match between the game show’s superstars Brad Rutter, Ken Jennings and James Holzhauer is in the books. The first to win three takes the title.

Three “Jeopardy!” champions — from left, James Holzhauer, Ken Jennings and Brad Rutter — are competing for the title of “greatest of all time.”
Three “Jeopardy!” champions — from left, James Holzhauer, Ken Jennings and Brad Rutter — are competing for the title of “greatest of all time.”Credit...Eric McCandless/ABC

In the first game of the first match of the three biggest “Jeopardy!” stars, Ken Jennings bet everything he had on a Daily Double despite muttering seconds earlier that the category, in which each clue actually contained three clues, was “not where I feel comfortable.”

Jennings gave a cautious but correct response, doubling his points and shooting past his opponents. He heaved a sigh of relief and said, “I don’t think I could do that again.”

But in the next game of Tuesday’s hourlong “Jeopardy!” match, Jennings did do that again, betting all that he had on a Daily Double and producing the correct response: Morgan le Fay, a character in a Mark Twain novel. He sped past the two other game show greats on either side of him, James Holzhauer and Brad Rutter, for an early lead.

The two-game match came down to Jennings and Holzhauer. Both correctly answered the two Final Jeopardy clues, about the first six words of the Gospel of John (What is “In the beginning was the word”?) and an astronomer whose name was given to a comet that crashed into Jupiter and whose remains are on the moon. (“Who is Shoemaker?”)

Jennings’s 16,600-point win in the first game allowed him to bet conservatively in the second Final Jeopardy, and despite Holzhauer’s victory in the second game, Jennings won the overall match by 200 points.

With that, Jennings took the early lead in the competition for the lofty title of the “greatest of all time.”

Over its decades on air, “Jeopardy!” has become adept at finding ways to bring back its biggest stars, like “Star Wars” and Marvel do on the big screen.

Jennings, who holds the longest streak in the show’s history with 74 consecutive wins, has returned to the franchise numerous times: the Ultimate Tournament of Champions, the All-Star Games, the Battle of the Decades, a competition against I.B.M.’s Watson computer. Rutter holds the record for overall winnings, $4.7 million, amassed over years of winning these all-star tournaments.

Holzhauer holds the other major “Jeopardy!” record: most money won in a single game ($131,127), and he also has the next 15 highest totals, all accomplished during his 32-game winning streak last year.

In a series of primetime hourlong episodes that began airing on ABC on Tuesday, they are playing one another in two complete “Jeopardy!” games each night. Each contestant’s combined score in the two games determines who wins the match, and the tournament will continue until someone wins three matches. The champion will receive $1 million and the sweeping title of “greatest of all time.” The runners-up will each receive $250,000.

“I think it really is a tossup between the three players,” Andy Saunders, who runs a website called The “Jeopardy!” Fan that tracks players’ statistics, said before the first match aired. “All three of them have strengths and weaknesses. You never know what might happen.”

The matches, which were prerecorded, airs again on Wednesday and Thursday at 8 p.m. Eastern time, 7 Central and Mountain and 8 Pacific. It will continue into next week if no one wins three matches this week.

Here’s a look at each player.

Twenty years ago, Rutter left the “Jeopardy!” studio having won more than $55,000 and two Chevy Camaros. Rutter hadn’t lost a match, but at that time, contestants were kicked off after winning five straight games.

So Rutter went back to his job at a record store in Lancaster, Pa., gave the green Camaro to his brother and kept the silver one for himself. But Rutter would eventually return to “Jeopardy!”: In 2001, he was invited back to compete in the Tournament of Champions; then again, in 2002, for a separate series. He would go on to amass $4.7 million in winnings, the most overall for any contestant.

Because he was limited to five games at first, Rutter didn’t get the same fanfare in the media as Holzhauer or Jennings, who appeared on the show after the victory limit was eliminated. As a result, his name is sometimes forgotten in conversations about the “Jeopardy!” greats. A win during this tournament would certainly change that.

“It bothers my friends a lot more than it bothers me,” Rutter, 41, said in an interview on Monday. “They’ll go ballistic about it.”

Rutter quit his job at the record store after he won his first “Jeopardy!” Tournament of Champions in 2001, taking home $100,000. The next year, he multiplied his winnings at the show’s Million Dollar Masters tournament at Radio City Music Hall. He took home $1 million, the largest prize in the show’s history at that point.

The tournament invites kept coming — as the show’s biggest cash winner, Rutter was a natural choice.

“Every time a new challenger comes up, if someone gets hot in the media again, that probably means they’ll have another big all-star tournament, so I’ll get to play,” Rutter said.

“Jeopardy!” likes to say that Rutter has never lost to a human opponent, referencing his loss to Watson in 2011.

Eventually, Rutter left Pennsylvania to pursue acting and producing in Los Angeles. He was involved with a couple of television pilots that never got picked up, like one about the misadventures of the employees at a poorly run fitness club. Rutter was also an executive producer on “The Bitter Buddha,” a documentary about the comedian Eddie Pepitone, which was selected for several film festivals.

With his frequent attendance at “Jeopardy!” tournaments, Rutter has the advantage of having faced some of the best players that “Jeopardy!” has ever seen, according to Saunders. But he also tends to win in narrow scrapes. At the 2002 tournament at Radio City, Rutter won by $1 after all three contestants got the Final Jeopardy question correct.

Jennings, 45, is known for his endurance. His 74-game winning streak in 2004 remains unsurpassed.

Jennings, whose fans call him “KenJen,” has also held onto his record for the most winnings during a regular season, having amassed $2.5 million. Holzhauer could have overtaken Jennings on his 33rd game had Emma Boettcher, a University of Chicago librarian, not defeated him.

Saunders has noticed that Jennings is particularly adept at more complex clues that require the contestant to make multiple connections in mere seconds. His weakness tends to be Final Jeopardy, which proved to be his downfall during his 75th game.

The clue that felled him: Most of this firm’s 70,000 seasonal white-collar employees work only four months a year. (The answer is at the bottom of the story.) Jennings answered incorrectly, giving up his title to Nancy Zerg.

Apart from his regular participation in “Jeopardy!” tournaments — which has increased his total winnings to $3.4 million — Jennings has turned his game-show stardom into the writing career he dreamed of when he was a 29-year-old working as a computer programmer to pay the bills. He has written a book about trivia culture, a history of humor, a children’s guide to Greek mythology and more.

“The main thing that the show got me, honestly, is that I don’t work a 9-to-5 anymore,” Jennings told The New York Times last year.

Fresh from playing dozens of games just last year, Holzhauer, 35, has a natural edge. His most recent performance, in which he won a rematch with Boettcher, aired in November, and this tournament was prerecorded in early December. (Jennings and Rutter also appeared on the show in 2019 during the All-Star Games.)

It was Holzhauer’s ability to hunt down the Daily Doubles and successfully bet all of his money that seemed to fuel his streak. In April, Holzhauer set the record for the most money won in a single game ($110,914); he went on to beat it three more times. A hand gesture — as if Holzhauer was pushing his poker chips into the middle — came to signal to the host Alex Trebek that Holzhauer was going all in.

Another thing that sets Holzhauer apart, Saunders said, is his buzzer strategy. Jennings and Rutter have both said that they track the cadence of Trebek’s voice to know when to push the hand-held button, but Holzhauer has said he focuses on visual cues — waiting for the lights on the sides of the game board to turn on, which indicates that the contestants can buzz in.

That approach — which comes from the book “Secrets of the Buzzer” by Fritz Holznagel, another repeat “Jeopardy!” winner — could be advantageous when Trebek gives unusually short clues that defy the usual cadence of the question, Saunders said.

Since winning big — he has earned $2.7 million in total — Holzhauer returned to his day job of sports betting in Las Vegas.

But, like the game-show greats who came before him, Holzhauer may be ready to expand his celebrity past the “Jeopardy!” stage, noting in a recent tweet that his noncompete agreement with the show runs out this month.

(Answer: What is H&R Block?)