Former failed 'Jeopardy!' contestants return to the show and talk about the effects of losing, and then lose again

Jeopardy! kicked off its 40th season amid a writers strike Monday, returning to the airwaves with both recycled questions and recycled contestants with a series of “Second Chance” episodes.

Given the ongoing strike, the show decided to return to action using reused questions, but according to executive producer Michael Davies, they only wanted to do that if they also featured past contestants.

As host Ken Jennings explained, the show is inviting back 27 contestants over the next three weeks, with nine playing each week during the initial three games, and the winners advancing to a two-game, total-point final to round out the week. The champion of that will advance to the first-ever Champions Wild Card Tournament later in the fall.

Jennings described the contestants that were chosen as those whose “first games may not have ended in victory, but their strong play showed us that they are indeed worthy of a second chance.”

And two of those contestants just so happen to speak about the effects of a near-win in Jeopardy! on their lives, and both will unfortunately have to deal with those feelings all over again.

One of them is Derek Allen, an accountant from Cassopolis, Michigan, who originally came in 3rd place in the June 7, 2021 episode with a score of $0, going out on a clue related to the late actress Vivian Leigh. Jennings asked if he was “a little bit haunted” by the Final Jeopardy! clue that ended his chances.

“I will never forget Vivian Leigh for as long as I live,” Allen said, before adding a positive spin. “But if I’d gotten that question right and won a game, I wouldn’t have the chance to come back here.”

But the host pressed the issue a bit, asking if seeing old clips of the star in films like A Streetcar Named Desire leaves him “a bit traumatized.”

“I don’t forget. Let’s just put it like that,” Allen said.

Jennings then referenced his very first loss on the show by saying, “exactly. Every time I drive by an H&R Block, Derek….”

Another returning contestant was Gabriel Ostler, a scriptwriter from Orinda, California, who originally placed third in the November 27, 2020 episode with a total of $2. Jennings asked him what his “recovery period” was like.

“It was about a year, I would say, where I could not see the blues or the category,” Ostler said of the show’s set pieces. “My family — I grew up watching it with them — they would still like to partake from time to time and I would just be like, ‘okay I gotta retire to my chambers, I can't watch this right now.’”

Jennings followed up by asking if he was “triggered” by being surrounded by the blue set on Monday.

“The heart rate is elevated for sure. But we’re taking some deep breaths and getting more into it,” Ostler responded.

The third contestant was an operations manager from Mulino, Oregon named Jill Tucker, who originally placed third in the January 28, 2021 episode with a score of $21,100. She decided to, perhaps wisely, speak about a different topic instead during her interview portion and went on to win Monday’s game. She went into Final Jeopardy! with the lead and doubled her money to $32,400 for the day.

Ostler got the final clue wrong and finished with $0 for third place, while Allen’s $16,201 was only good enough for second place after getting the final question right. And now the new person who will be haunting their dreams: Queen Victoria.

But depending on how long the writer's strike goes, maybe there will be a Third Chance tournament.

Jeopardy! airs weeknights, check your local listings.