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Unstoppable Confession! The ‘Jeopardy!’ Contestant Who Crushed The Competition Breaks Silence: Was Their Shocking, Runaway Win Pure Skill or Just Luck?

‘Jeopardy!’ Contestant Speaks Out After Runaway Win

(from left) 'Jeopardy!' players Jonathan Goldman, Steven Olson, and David Shutoff on September 22, 2025

Spoiler Alert

Jeopardy.com

[Warning: The following post contains MAJOR spoilers for the Monday, September 22, episode of Jeopardy!]

Jeopardy! contestant Steven Olson returned for his second game on September 22 and spoke out about how he prepared for the game show and his experience on it. The game was another runaway win between the three contestants.

Olson, from Princeton, Illinois, played against Jonathan Goldman, from Palm Beach Gardens, Florida, and David Shutoff, from Salem, Massachusetts, after winning $19,602 in his first game. Olson teaches at a high school and a middle school, and he shares a classroom with his wife, who is also a music teacher.

Olson, a band director, took the lead during the beginning of the round, despite two triple stumpers, and Shutoff, a product development manager, sneaking in a few answers. The reigning champion found the Daily Double on clue 10.

With $1,300 in his bank, he made it a true Daily Double. In “King James Bible Talk,” the clue read, “The KJV loves this synonym for ‘strike’ or ‘bash’, as in ‘thou shalt’ do this to ‘the rock, and there shall come water out of it.’” Olson correctly answered with “What is Smite?” and doubled to $2,600.

By the end of the round, he maintained the lead with $10,200. Shutoff had $3,000. Goldman, a futures trader, trailed with $2,200.

In Double Jeopardy, Olson found the first DD and made a risky wager. With $15,000, he wagered $7,000 in “Asian Cities.” The clue was “This Lebanese city was created when 3 sections settled by people from Tyre, Sidon & Arvad merged into one city.” After being prompted by host Ken Jennings to give an answer, Olson said, “What’s Beirut?” He was wrong and dropped down to $8,000. The correct response was “What is Tripoli?”

It was a battle between Olson and Shutoff until Olson found the second DD of the round. From his total of $10,800, Olson wagered $4,000. The clue in “‘Cross’ Words & Phrases,” read “This act by Julius Caesar in 49 B.C. led to war against Pompey & the Senate.” He correctly answered with “What is crossing the Rubicon?” and took a big lead of $14,800.

Although Shutoff and Goldman put up a fair fight, Olson came out on top with $20,400. Shutoff was in second with $13,400. Goldman had $7,400 going into Final Jeopardy.

The Final Jeopardy question in the category “Political History” wasn’t so easy for all of the contestants. It read, “The words of this doctrine are found in a sonnet by James I & bolstered by St. Paul writing, ‘the powers that be are ordained by god.’” The correct response was “What is the Divine Right of Kings?” which only one of them said.

Goldman’s response was, “What Divine? Hi Eric + Lily.” He stayed at $7,400 after wagering $0. Shutoff thought it was the Monroe Doctrine and had a final total of $6,399 after wagering $7,001. Olson got it right, writing “What is Divine right of kings?” He won the game with $26,804 after wagering $6,404. Olson will return for game three on Tuesday, September 22.

After his first win, Olson spoke with his alma mater, Western Illinois University, about his time on the game show. “I’ve watched Jeopardy! consistently since I was a kid, and so it was an absolute dream come true,” he told the college, which he graduated from in 2015.

“I was lucky to have the summer off leading up to my taping, so I did do some preparation. Ken Jennings is every bit as nice and funny as you would expect.” After going through the process every contestant does to audition, Olson spent his summer making his own games of Jeopardy! and brushing up on categories he wasn’t too strong in.

However, once he stepped onto the stage, Olson didn’t believe it until he heard his name called. “It was very surreal to walk into the stage that I’ve seen so many times on TV and see it in real life,” he said. “The team at Jeopardy! was extremely welcoming, and I really enjoyed meeting the other contestants from my tape day and talking to them throughout the day. Walking on stage and being announced as a contestant was indescribable. I was as stressed as I have ever been in my life.”

The opportunity was even more special because he used to watch Jeopardy! with his mom, who died about a year ago, according to his local news station, KWQC. “I lost my mom last year,” he told the outlet. “We did a lot of that together. My love of reading and my knowledge of stuff started there. So, I know she’d be very proud of me.”

Jeopardy!, weekdays, check local listings, stream next day on Hulu and Peacock

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