Quick Take

Santa Cruz's Jackie Rogoff embarked on a "Jeopardy!" journey, never expecting she might win. But she did.

This midwinter season, Lookout Santa Cruz is checking in with some of the people and topics we’ve covered over the past year.

On a Monday night last June, a celebrated but recently deceased Santa Cruz-based author was mentioned as a clue on the country’s most enduring game show, “Jeopardy!” The clue: “Jeanne Wakatsuki Houston told of her Japanese American family’s internment during World War II in her memoir ‘Farewell to’ this place.” 

For locals, it was remarkable enough that Houston – a beloved figure in Bay Area literary circles who died in December 2024 – surfaced on the big board at “Jeopardy!” But it was nothing short of astonishing that the contestant who responded correctly to that clue (“What is Manzanar?”) was also a writer from Santa Cruz. What are the odds?

That contestant was Jackie Rogoff, who won her round that June night, which meant she got to return the following evening as a “Jeopardy!” champion (alas, she lost that second time out). 

Rogoff, a student at San Jose State University and aspiring writer, took up trivia as a pandemic hobby, participating in an online trivia league. Inspired by a friend who had a lifelong wish to be a “Jeopardy!” contestant, she decided to take the show’s online test herself. She did well enough that she was contacted by the show’s producers to take the next step in the screening process. After another test, this one live on Zoom, a mock game in front of cameras and an interview, she was put in the pool of eligible would-be contestants. She got the invitation to take the stage at “Jeopardy!” in Los Angeles in February, shot her games in April, and watched with the rest of us in June.

Unlike many who try out for the show, Rogoff said she had never been a consistent fan of “Jeopardy!” 

“I did watch a taping in high school,” she said. “I grew up in New Jersey, and we took a field trip to L.A., and one of the activities we did was to go watch ‘Jeopardy!’ I remember thinking it felt really fast in person in the audience. But I didn’t feel that way playing it.”

Rogoff, who has degrees from the Massachusetts Institute of Technology and Stanford University, worked in tech in Silicon Valley for about a decade before changing course to become a science-fiction writer. She’s pursuing a library science degree at SJSU. 

Being a student of information systems was a plus in her preparation for appearing on “Jeopardy!”, she said. After her invite to the show, she was introduced to the complex and challenging world of “Jeopardy!” prep.

“So there’s the general knowledge part,” she said, “there’s the buzzer, and then there’s the wagering strategy. And those were three things I had to figure out.”

On the internet, she found guides solely for how to play the show’s Daily Doubles, which also provided insights into how the hidden Daily Doubles are usually distributed on the board. She purchased a 60-page e-book on buzzer technique. She found an online archive of every “Jeopardy!” clue, which she felt she had to study in hopes of anticipating what categories she might have to face. Gradually, she began to learn some of the secrets of succeeding at “Jeopardy!”, that the Daily Doubles are most likely to appear in the fourth row, that history and literature are subjects the game goes back to again and again, that there’s a method to master being the first to hit the signaling device, as well as a mathematical formula for betting on Final Jeopardy. 

“I was motivated for not wanting to look dumb,” she said, “for missing that question that everyone else learned in high school.”

Rogoff didn’t expect to win her round. But she did. 

“When I was prepping, I really didn’t think, ‘What if I win?'”

At the end of her first game, she had won more than $22,000, been named a “Jeopardy!” champion and was invited back to defend her title in the next game. In real time, “Jeopardy!” records up to five episodes a day, so the time between winning her first game and having to compete in the second game was about 10 minutes, not much time to savor a victory. 

Santa Cruz writer Jackie Rogoff, contestant on "Jeopardy!"
Santa Cruz writer Jackie Rogoff on her experience on “Jeopardy!”: “I was motivated for not wanting to look dumb, for missing that question that everyone else learned in high school.” Credit: "Jeopardy!"

“You leave the stage,” she said. “The audio guy takes your mic. At least [the winning player] gets priority for the bathroom. So it’s like bathroom, chug some tea or water, have a couple of crackers or something.”

She also had to spend much of that time changing clothes for the next episode. She had brought an entire suitcase of different outfits, which was screened by the show’s production staff. A staffer told her that the clothes she chose to bring were perhaps a bit too dark for the spring. 

“When I came back from hair and makeup [before the second game], there’s like a bunch of random clothes hanging in my [dressing area].” The top she wore for her second game wasn’t her own.

She lost that second game, but was more relaxed on the set. The only moment she felt anxiety was during the obligatory but brief get-to-know-you interview segment near the beginning of the show. Host Ken Jennings, noting her interest in science fiction and library science, asked her to recommend a book. That can be a complex question to ask a writer, and Rogoff “panicked” and picked out of the ether Ursula Le Guin’s “Left Hand of Darkness.”

“I still stand by it,” she said. “But asking to recommend a book to someone on the spot, on TV, with millions of people watching, and it’s also Ken Jennings, well, it was hard.”

The recording of Rogoff’s two games of “Jeopardy!” were witnessed by her father, her husband and the friend who inspired her to try out for the show. For two months, Rogoff and her traveling party were sworn to secrecy on the outcome of her “Jeopardy!” experience: “I didn’t even tell my mom.”

The experience culminated in the June 8 and 9 broadcasts, the first of which was a party in her honor at a friend’s house in the Bay Area. The second show she watched with a few friends at her home in Santa Cruz.

She’s been recognized a couple of times in public for her moment on “Jeopardy!” Some day, she hopes to be recognized on a different plane, as a science-fiction writer. For now, she’s living the writer’s life, fleshing out ideas, working on her craft, going to workshops, collecting rejection letters from editors. 

Because she once worked in tech, she is interested in “near future” fables and what they might say about how technology may change human intention and behavior. 

“I want to write,” she said. “I quit tech to focus on my writing and only my writing. So far, my ambition is to find a way to be productive.”

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Wallace reports and writes not only across his familiar areas of deep interest — including arts, entertainment and culture — but also is chronicling for Lookout the challenges the people of Santa Cruz...