JEOPARDY! host Ken Jennings was caught on camera cringing after a contestant made a game-losing wager on a failed Daily Double attempt.

The risky move didn’t pay off for the newcomer – who lost his lead and helped returning champion Greg Jolin sail into his third consecutive victory.

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Ken Jennings hosts Monday’s game of Jeopardy!Credit: Jeopardy!

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Brian Frey cringes as he misses his third Daily Double clue on Jeopardy!Credit: Jeopardy!

The system specialist from New Hampshire went up against Brian Frey, a journeyman originally from Syosset, New York and Lindsey Simmons, an attorney originally from Marshall, Missouri.

In a nail-biting game, Brian and Greg swapped leads as the ultimate outcome was determined by the Daily Doubles.

Brian found the first DD under the “Quotable Oscar Wilde” as Ken read out the clue.

“This watery site ‘must be one of the earliest, if not the keenest, disappointments in American married life,’” the host said.

Brian bet all of his $3,000 on a true Daily Double, but was not able to correctly guess: “What is Niagra Falls?”

Despite the cringe expression from Ken and the disappointment from Brian, the game was still early as he attempted to make a comeback.

He had better luck when Brian found the third Daily Double under “World Flags” and once again wagered $3,000.

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From left to right: Greg Jolin, Lindsey Simmons and Brian FreyCredit: Jeopardy!
“The four stars on Tokelau’s flag represent this constellation and the role of Christianity in the country’s culture,” Ken read.

This time, Brian correctly guessed “What is Southern Cross?” doubling his total to $6,000.

With the big gamble paying off, he was able to get closer to Greg’s lead total of $9,000.

Rounding out his trio of findings, Brian was able to also sniff out the third Daily Double – betting nearly all of his fortune in hopes of surpassing Greg’s lead.

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Under the category “Epics,” the clue read: “No one-trick pony, Finder, who starred in “Seabiscuit”, also played Joey in this World War I epic.”

Brian failed to guess “What is War Horse?” and wagered $5,000 of his $6,000 total – dropping to just $1,000 while Greg maintained his lead of $10,600.

The costly third mistake led to Greg’s runaway lead – and a noticeable grunt from Ken that made the host appear to feel bad for the contestant’s rough gameplay.

Heading into the last round, Greg stayed in first with $19,000 while Brian dropped to third with just $3,800.

Lindsey was in the red part of the game but was quick with the buzzer – earning her $5,600 by the Final Jeopardy! round.

Ken introduced the final category as “19th Century Lit” as Ken read the clue: “All introduced in the same chapter of a novel, Grimaud, Mousqueton & Bazin are the servants of these men.”

Both Greg and Brian were correct – with the returning champ adding $6,000 to his score for a game-three total of $25,000.

Greg’s three-day earnings have accumulated to $75,002 as he heads into a crucial game four on Tuesday.

Jeopardy! Contestant Rules

Passing Jeopardy!’s online Anytime Test is hard enough, but there are also many rules players must follow once they make it to the stage:

The returning champion is always at the leftmost podium and keeps playing until they lose.
Contestants don’t have to say “who is” or “what is” in the first round but must do so in Double Jeopardy! and Final Jeopardy.
Contestants can change their responses as long as Ken Jennings or the judges haven’t made a ruling.
The minimum wager for a Daily Double is $5. The minimum wager for Final Jeopardy! is $0.
Written responses in Final Jeopardy! do not have to be spelled correctly, but they must be phonetically correct (the judges decide this).
If there’s a tie after Final Jeopardy, the tied players enter a bonus clue shootout, and whoever buzzes in first correctly wins.
If all three contestants wager everything in Final Jeopardy! and are incorrect, leaving them with $0, there will be no returning champion (it’s happened before—six times).

Brian anded the game with $7,599 while Lindsey had $3,399 when the episode concluded.

Viewers sounded off online after the game and emphasized the importance of the Daily Doubles, with one writing: “The game seemed to go to an interesting fashion, until an incorrect response by Brian in that Daily Double.

“Which in turn took the wind out of Brian’s sails, allowing Greg to cruise to his third victory. It goes to show how important are those Daily Doubles, as they have the power to change the tone of the game.

“Will Greg get the all important win no. 4 and an invitation to the TOC tomorrow? Well tune in tomorrow to find out.”

Another said: “Yikes those Daily Doubles got the best of Brian. Still a good game, man!”

Greg needs to secure just one more win to most likely solidify his spot on Tournament of Champions.

However, scoring a 5th win would guarantee his invite – being only the second contestant behind Mark Fitzpatrick to make the cut in season 41.

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Brian’s game was determined by finding all three Daily DoublesCredit: Jeopardy!

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Greg has secured his third-straight Jeopardy! victoryCredit: Jeopardy!