Breaking Brad: Why Brad Rutter Is Losing Jeopardy’s GOAT Tournament

Ken Jennings and James Holzhauer are running circles around the winningest game show contestant ever on Jeopardy: The Greatest of All Time.
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Image: Jeopardy

After three episodes of Jeopardy’s Greatest of All Time (GOAT) tournament, the question on everyone’s mind is: Why is Brad Rutter losing?

It has to do with Daily Doubles, the clues that let you wager your entire score—or up to $1,000 in the first round or $2,000 in the second round, whichever is higher.

Rutter, the person who has won the most money in all of American game-show history, has managed to snag 50 percent of the 18 Daily Doubles across six games in the first three matchups. However, he’s answered correctly just one-third of the time. In the GOAT tournament, Rutter has lost games of Jeopardy to human opponents for the first time in his career. (He has $4,788,436 in earnings from five regular-season episodes, five tournament wins, a third-place to IBM’s Watson, and $100,000 from other game-show appearances.)


Update: Ken Jennings has won the entire tournament.

Of his opponents, Ken Jennings (the biggest regular season winner with the longest run of shows) has grabbed four DDs and been right on each. The third grandmaster, James Holzhauer (just shy of Jennings’s winnings and at over twice the earning pace), has picked up five DDs and was correct on four of those five.

We need to be kind to Rutter, as my family is when we watch at home—this is Jeopardy at its highest level, and with immense pressure. While he’s beaten Jennings several times, he’s never played against the equivalent of two Kens at once.

What is out of my depth, Alex?

I played Jeopardy in 2012 and won twice—and let me add, by the skin of my teeth. I was happy to go home with over $30,000 and a picture of me and Alex Trebek.

I learned before and during my games that Jeopardy is not just about trivia. Contestants are selected in part for knowledge, and usually two or three of the players know a given answer. At the GOAT level, outside of Daily Double and Final Jeopardy stumpers, all three champions likely know the answer.

This is where betting and odds knowledge come in as a critical additional aspect. With control of the board, all three players are hunting for those DDs, as only the player with the ability to select can answer a Daily Double.

The producers typically place DDs as the third or higher of the five clues for each category (the $600 position in the Jeopardy round and $1,200 in Double Jeopardy). As clues disappear, the GOAT players are balancing their knowledge of a category with the potential to block a competitor by grabbing a DD and even betting on the low side if they aren’t confident, or to obtain the advantage by betting high and winning. (Arthur Chu gained a lot of enmity for aggressively playing across the board and hunting DDs, because some viewers decided it wasn’t a “fair” way to play, though given white players had chosen that route starting in 1985 and employed it since without much controversy, it seemed a lot more about race.)


In normal play, contestants may be hesitant when the Daily Double razzmatazz sound plays, one of the few sound effects Jeopardy employs. When you’re behind, it’s easy to fear a wrong answer would cost you the game; while ahead, wagering conservatively could advance your lead if correct while not knocking you out if in error.

Holzhauer went for broke nearly every time in his regular-season games. He bet most or all of the amount he had on the board, a strategy employed most aggressively previously by Roger Craig, an all-time champ who beat Jennings’ one-day score of $75,000 by racking up $77,000. Holzhauer across his weeks of play took the one-day title, too—he now holds the top 16 positions with his highest being $131,127.

That’s required Jennings and Rutter, never shy in the past from all-in bets, to hit hard when they capture a Daily Double question. It’s like watching a set of sharks hunting a small school of tuna: the first one in gobbles them all, leaving the others hungry.

The questions so far have been GOAT-worthy, especially Rutter's Daily Doubles. Watching the first game of the first day’s match, I was gobsmacked by how few clues I could answer in the form of questions, even as contestants whipped out answers faster than I could read them.

In the first game on that first day, Rutter had the clue in the “Dancing with the Czars” category: “‘We understood each other…& let the others prattle,’ said Catherine the Great of this longtime adviser & less longtime lover.” Rutter struggled for an answer and came up with Vronsky, a fictional character from Anna Karennina. The correct response was, “Who is Grigory Potemkin?”


In the second game, Rutter reasonably choked in Double Jeopardy on Daily Doubles for “Born in New Orleans, Louis Armstrong performed songs named for these 2 local “B” streets” (Bourbon and Basin; he said Bourbon and Beale, as I did, though I knew Beale Street was in Memphis) and “This double-first-name philosopher born in 1842 said that the value of a concept is in its practical consequences” (William James). These two incorrect responses reset his score to zero—twice! Even still, he clawed his way back to 10,000 points by Final Jeopardy, within striking distance of the other two players.

Because Rutter had cleared out so many DDs, Jennings and Holzhauer are engaged in a fight to grab toeholds in a rock face they’re climbing instead of taking an elevator to the top. And when they have gotten DDs, both Jennings and Holzhauer have capitalized in a way Rutter hasn't.

Just as important as finding and correctly answering Daily Doubles is finding them at the right time. Rutter has only been correct on Daily Double wagers at times when he had little to bet, often not even the 1,000- or 2,000-point alternate bet for each round.

Buzzer Timing

Rutter has seemingly demonstrated an additional disadvantage, one not seen in his previous gameplay. In addition to getting Daily Doubles wrong, Jeopardy is a game of millisecond-level reflex response. Press the button on the signal device before a producer has decided Alex has finished reading the clue and unlocked the “buzzers” (signal devices, really) and you’re briefly locked out. Click a millisecond too late in the GOAT gathering, and another of your razor-sharp competitors has won the race and gives the answer.

When the producer presses their button, lights illuminate to the left and right of the stage game board out of view the television audience’s frame. Jennings and many other champions say they rely on Trebek’s cadence to buzz in; I followed that advice, notably from the book Prisoner of Trebekistan, by another multi-tournament champion, Bob Harris. Holzhauer followed a previous champion’s advice and looks for the lights.


In the six games played so far in this tournament, Rutter has won the buzzer toss-up by far the least. With 57 questions up for grabs in each game—30 plus 30 less three Daily Doubles—Rutter has answered 10 to 12 questions for five of the six games. Jennings and Holzhauer have on average divided the rest with a slight advantage in each direction, depending on the game.

That brings us to the last overlooked element of Jeopardy play: ringing in without being sure you had the correct answer. With a Daily Double, you can bet as little as $5 if you hate the category, but few people do, and none of the GOAT contestants can afford to. (I won my first game of Jeopardy because the returning champion spoiled her run-away win by betting too much on a late-game DD—she should have wagered $5.)

With other clues, you have a moment while Trebek reads the text to figure out if you should ring in. If you answer with the wrong question, you lose that dollar amount, which can put you into the negative. Rutter’s has been wrong on 11.4 percent of his regular-question responses, while Holzhauer is at 8.1 percent and Jennings at 6.8 percent. That slight difference, coupled with Jennings's 100 percent correct responses for the Daily Doubles he’s hit tells the story of how the competition is going, though not why.

I stood at the podium three times, winning two games and a meager $31,000 or so by grandmaster standards, and I can tell you that each game is a fresh challenge and a fresh terror. I guessed my first Final Jeopardy correctly—ironically, “Who is Karl Marx?”—by elimination of other choices. I had the wrong answer but enough cash remaining to prevail in the second Final Jeopardy, vexing the only one of us three who was correct. I sealed my doom in my third game when I misspoke in a Daily Double and said “Who was George Sands?” rather than “George Sand.” (Trebek: “Ooo, sooorey.”)


I flailed in my third game, because I’d simply run out of steam. Jeopardy typically tapes five games a day, two days in a row. I had won games four and five of my first day in Culver City, and then lost game one of the second. My brain’s answering chemistry felt depleted. I saw a picture of a hibiscus, recognized it as that flower, and bizarrely said, “What is an orchid?” My sympathetic wife, who has a degree in horticulture, was supportive.

It’s an endurance contest in the best of times, and starting off on a bad pace can keep you down. We don’t know how rapidly they taped episodes for this tournament. In a typical tournament, even the final three players compete in no more than three games a day. With the two-game-per-match structure, it’s likely they taped two episodes a day or four games, to avoid the mental exhaustion of a fifth and sixth game in a row at this calibre.

They already got their GOATs

Without any advance knowledge, what’s happened so far makes it likely Jennings will win. With a slight edge in accuracy and maintaining a vigorous balance with Holzhauer on signaling, he only needs to win either one of the next two if Holzhauer prevails again, or in a dramatic showdown, Jennings can win any game up to the seventh match if Holzhauer wins just one more and Rutter picks up two.

My family is “#teamken,” because Jennings is local to us and I’ve met him a couple of times. He graciously gave me his insight in person before my first game, as did another local top winner, writer and bookstore owner Tom Nissley. But I always love the underdog, and would love to see Rutter fight back to his obvious potential.


If Jennings wins this tournament, he would also take the title of all-time American game-show cash winner from Rutter with $5,223,414 to Rutter’s $5,138,436, as Jennings has won bundles on other programs.

Nonetheless, Rutter, Jennings, and Holzhauer should each keep the GOAT mantle after this competition. The next runner-up in each of their scoreboard categories at Jeopardy are far behind, as great as that tranche of players are.

Regardless of who wins, Jeopardy GOAT has been a lot of wholesome fun. Trebek revealed he was in treatment for pancreatic cancer in early 2019, and that he had to resume treatment later in the year, making this tournament and all we Jeopardy contestants’ experiences all the more tinged with worry and nostalgia. His last games are approaching or maybe already quietly taped, too.

Producers guessed viewers wanted to know who was the ultimate winner, but I think getting to see the pinnacle of modern quiz-show performance provides just as corny and lovable an answer as the tradition of Jeopardy itself: It’s us, the viewers. We’re the winners.

Glenn Fleishman is a two-time Jeopardy champion and a veteran technology reporter who contributes to the Economist, Fast Company, Macworld, and many others. He’s also a type historian, currently assembling a set of one hundred tiny type museums, sets of historical and modern printing artifacts. He can be found at @glennf on Twitter and on the web.