Sandy Olive (right), an English teacher at Lindbergh High School and graduate of the UMSL College of Education and College of Arts and Sciences, appeared on three episodes of “Jeopardy!” last week. NBC’s Savannah Guthrie (left) guest hosted the show. During Olive’s run, she was a two-day champion and won more than $50,000 in prize money. (Photo courtesy of Jeopardy Productions, Inc.)
Sandy Olive has been a “Jeopardy!” fan most of her life.
“I used to DVR it and stockpile the episodes until I had 50 episodes,” she said. “My niece would come over, and we would spend an entire Saturday just blowing through episode after episode.”
The ritual helped Olive, a graduate of the University of Missouri–St. Louis College of Education and College of Arts and Sciences, as well as sophomore English teacher at Lindbergh High School, prepare for her recent three-episode run on the classic TV game show.
Olive started strong in her debut last Tuesday, dethroning the returning champion in an episode guest-hosted by NBC’s Savannah Guthrie. She is just the latest Triton to appear on the show. Alumnae Mary Grace Buckley and Seema Dahlheimer were contestants in 2017 and 2019, respectively, and there could be others.
In the first match, Olive went into Final Jeopardy with $21,000 – far enough ahead of her opponents that she didn’t need to wager anything. She turned in an equally impressive performance on Wednesday, earning $10,000 during the first round and entering Final Jeopardy with $19,200.
Despite the impressive figure, a challenger trailed by $3,800. She preserved her place as champion by correctly naming Valentina Tereshkova as the Russian woman who appeared on a ruble coin in 1983.
Olive’s $12,000 wager on the question pushed her two-day total to $52,000, and she took that momentum into Thursday’s contest. Olive took an early lead and closed the first round with a string of correct answers. After Double Jeopardy, she was still leading with $19,200.
Unfortunately, during Final Jeopardy, she could not identify the 19th Century American author who penned a novel with chapter titles including, “Camelot,” “The Pilgrims” and “A Postscript by Clarence.” Ironically, it was Missouri’s most famous author, Mark Twain, in “A Connecticut Yankee in King Arthur’s Court.”
“I always knew that there would be that cruel irony of me getting out on a literature question, and then there it was,” Olive said. “It feels so obvious now, but they could have kept me in that room for 1,000 years and I never would have gotten it. I probably would have gone through every single American author I knew, or every single 19th century author, and still not gotten it.”
Though her run ended, she couldn’t have asked for a better experience.
“I won that first game, and I just thought, ‘How can I ask for more?’” Olive said. “My goal was to have fun and just enjoy being there. It would be so greedy to ask for more.”
It was a dream come true – one that was more than 10 years in the making.
Before going back to school to pursue her bachelor’s in education at UMSL, Olive started writing, producing and hosting one of the first bar trivia nights in St. Louis at Lemmons. By the time she graduated in 2011, she had been taking Jeopardy’s online entrance test for several years. Her first chance at appearing on the show came as she was participating in the College of Education’s China Student Teaching program while finishing her education degree.
Olive got an email about auditioning while she was in China and tried out for the show when she returned. But she didn’t make the cut the first time. Still, Olive kept taking the online test over and over, which she says is the secret to eventually becoming a contestant.
She wasn’t quite prepared to get a second chance, though.
“I had about three weeks to let it settle in before I went, but I was just like, ‘This is crazy,’” she said. “It’s a thing I’ve been wanting my whole life, and then it felt like somebody just handed it to me.”
Friends and family told Olive that she seemed especially calm during her episodes. She explained that’s not normally her demeanor, but she viewed making it to the show as a once-in-a-lifetime opportunity no matter what happened. She realized that she wasn’t afraid to lose, and that mindset allowed her to remain focused during her run.
Others asked about her preparation, but Olive noted it’s difficult to prepare for the “sum total of human knowledge.” She brushed up on world capitals, which was a weak spot in her general knowledge. But, aside from that, she had a simple strategy going into the March episode tapings.
“I made two decisions,” Olive said. “One was not to ring in if I did not know – no guessing. The other was if I got a Daily Double. They were my biggest fear. I know a lot of people use them to bump that total up, but I bet $2,000 each time. I wanted to be able to control as much as I could. I didn’t want to leave it up to chance, so I decided a $2,000 max wager.”
The strategy paid off, but the experience interacting with fellow contestants was equally rewarding. She found that there was more of a sense of camaraderie than competitiveness during the tapings.
In particular, Olive recalls eating lunch with Michael Tran, whom she unseated as champion during her first episode. They discussed what they would do with their respective prize money.
Olive knew exactly what hers would go toward: a trip to Europe with her sister that had to be rescheduled due to the pandemic. The pair will start in Ireland and travel through Northern Ireland, Scotland and England before ending the trip in France.
“It was going to be my sister’s first trip out of the country,” she said. “She’s my older sister, but she was like a little kid with the whole thing. She was so excited, and then we had to cancel it. It broke my heart.
“So, some of this money is going to go toward making this an even cooler trip than it was already going to be.”
