Leah Caglio and Sally Neumann seem smart and friendly, but don’t let that fool you: They’re a couple of trivia bullies.

The best friends and budding business partners have earned that status. They put themselves through the game show crucible and emerged “Jeopardy!” champions, a couple of brainy women who are the trivia equivalent of pool sharks, rolling the rubes dumb enough to cross them on a Tuesday night at their local tavern. 

When Caglio won $17,500 on April 28, she became one of more than 70 “Jeopardy!” champions who call Washington state home.

Leah Caglio, left, and Sally Neumann, sitting at Leah’s Seattle home April 20, are best friends who also happen to be “Jeopardy!” contestants. They have opened a small trivia business together to try and capitalize on their shared love of the game. The Seattle area has a large number of “Jeopardy!” alumni (including, of course, Ken Jennings). (Ellen M. Banner / The Seattle Times)
Leah Caglio, left, and Sally Neumann, sitting at Leah’s Seattle home April 20, are best friends who also happen to be “Jeopardy!” contestants. They have opened a small trivia business together to try and capitalize on their shared love of the game. The Seattle area has a large number of “Jeopardy!” alumni (including, of course, Ken Jennings). (Ellen M. Banner / The Seattle Times)

Caglio and Neumann have a third bestie, and since Caglio returned from shooting “Jeopardy!” in Los Angeles earlier this year after her thrilling last-question win, they’ve amped up the pressure on Melanya Materne to make her own run on the show and join the Washington state “Jeopardy!” alumni club. 

“She’s never been super into trivia,” Caglio said. “But now we are extremely peer pressuring her and training her because now she HAS to go on ‘Jeopardy!’”

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“She’s got to become a champ within the next year or she can’t sit with us anymore,” Neumann said.

Turns out, after years of taking a bit of a back seat role in their trivia friendship, Materne’s ready for the challenge.

“Especially watching how Leah studied for it and flying down to L.A. to support her, I’ve become much more interested in taking up the mantle, so to speak,” Materne said. “If nothing else, just to go on ‘Jeopardy!’ and say I was bullied into going on. I think I’ll be entertaining in the anecdote section at least.”

“There should just be a heavy sigh from her,” Neumann joked. 

Caglio and Neumann — and maybe someday soon Materne — are part of a proud and growing “Jeopardy!” tradition here in Washington, and especially in Seattle.

“Jeopardy!” producers have not kept track of winners’ hometowns over the show’s 37 seasons, a spokesperson for the show said. But the good folks over at the J! Archive have assembled about 20 years of complete records and partial results from earlier seasons that allow us a fairly accurate picture of what’s going on in the Evergreen State.

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It turns out Washington is a contestant hot spot for “Jeopardy!” More than 262 players who claimed Washington as their state of residency or birthplace have competed, and there are probably many more if you include years where records are incomplete or because a contestant doesn’t mention a tie to the state on the show.

With more than 137 contestants, Seattle is likely in the top tier of America’s best “Jeopardy!” cities (that aren’t located in California, where the show is produced), and Washingtonian champions have won more than $4.7 million on the show combined.

“Seattle per capita does bring in a lot of contestants,” said Andy Saunders, a founding archivist at the J! Archive, a database of questions and contestant outcomes. “It’s not the top city. I think Washington, D.C., punches above its weight. I would say a couple of other spots like Boston or Denver also kind of punch above their weight a little bit. But Seattle is definitely in the top five.”

D.C. is full of the big-brained people who move there to run our country. The Boston metro area is home to Harvard University and the Massachusetts Institute of Technology. And Denver?

“Denver is a surprising trivia hotbed,” Saunders said. “I know the national pub quiz company Geeks Who Drink, they’re based out of Denver, so there’s a big trivia tradition in Denver itself.

“Seattle has its own advantages, though.”

Like the rain. No kidding. Everyone agrees.

“I feel like Seattle represents on ‘Jeopardy!,’” said Ken Jennings, the game show’s G.O.A.T. “And probably for the reasons you’d expect: some combination of tech industry nerdiness and bad weather. Honestly, any indoor hobby is popular in Seattle. And, of course, people are inside watching ‘Jeopardy!’ I mean, it gets dark at 4 o’clock, so …”

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Perhaps the rain is the reason Washingtonians are also pretty good at the game: more than 25% of homegrown contestants win at least one game. 

Our state is also home to two of the regular season all-time money winners. No. 1, of course, is Jennings. He won more than $2.5 million during his record 74 consecutive wins in 2004 (and passed $4.3 million in career earnings after winning the $1 million “Jeopardy!: Greatest of All Time” tournament in January 2020).

“Jeopardy!” contestant and Seattleite Ken Jennings, won a record 74 consecutive games on the show, and has since completed a stint as a guest host. (Seth Wenig / The Associated Press)
“Jeopardy!” contestant and Seattleite Ken Jennings, won a record 74 consecutive games on the show, and has since completed a stint as a guest host. (Seth Wenig / The Associated Press)

Bookending the top 10 is Tom Nissley, whose $235,405 was originally No. 3 back in 2010 (he added an additional $105,000 in tournaments). He’s fallen to 10th over the last decade as gambling-minded contestants rewrote “Jeopardy!” strategy, steadily upping winning pots in recent years.

“So I’m clinging,” Nissley joked. “If anybody passes me, I won’t be on the website anymore. But I’m still there.” 

As owner of Phinney and Madison Books, Nissley is easy to find. Occasionally, aspiring “Jeopardy!” contestants track him down to ask his advice. He’s often surprised how many people are connected to the show.  

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“People come out of the woodwork once your radar is on: ‘Oh, you were on …,’” Nissley said. 

“That’s something I only found out after I was done. There’s this community around the show, which I never would have expected.”

Once they’ve been on the show, contestants all share a very similar experience. The game has been largely unchanged over its 37 years, only recently losing host Alex Trebek last November to pancreatic cancer.

“I always describe it as just like jury duty,” Nissley said. “You come in 12 strangers. It’s one of the most stressful things you’ve ever done. And you spend the day together sequestered. So it does feel like jury duty.”

Producers record five games a day. Names are drawn from a hat to determine who goes first and you play till you lose. 

“If you lose before lunch, you don’t get lunch,” Nissley said. “If you haven’t played or you have won, then they give you a $10 voucher at the Sony commissary — where you might see Seth Rogen.” 

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Nissley got two lunch vouchers, playing nine games over two days, and did indeed see Rogen. It was a grueling experience that left him even more amazed by Jennings’ record run.

“I think when I met Ken one of my first questions was, ‘How did you physically sustain it?’” Nissley said. “The mental concentration, the pressure, you’re standing up the whole time. It’s really draining. I lost on a Friday and I feel like if someone’s been on the show for a while and you see them on a Friday, you can sometimes tell how fried they are.”

Neumann can identify. She won $11,900 in 2016 at age 25, and was overcome with emotion at reaching a life goal.

“They make you play five minutes later and I freaked out,” Neumann said. “I achieved my dream and then I blacked out the whole second game.”

Regardless, she inspired Caglio to set a goal and chase her own dream as well. Trivia was always at the heart of their friendship.

“I befriended Leah because she was always in the back doing a crossword puzzle like the bad kid,” Neumann said. “I was like, ‘Yeah, I want to be friends with her. That’s awesome.’ And then we would sit in the back and do crosswords together, not knowing how that would help us in our future trivia careers.”

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Materne eventually joined their back row clique, unaware of the taunting she was signing up for at the time. 

“We’ve been friends since college and trivia’s always been a part of it,” she said. “We started doing trivia at Shultzy’s in the U District, so it’s all pretty lighthearted. I try to rib them back and say if they want me to go on, they’re going to be tasked with training me ‘Rocky’-style.”

That’s exactly how Caglio attacked it when she finally decided to get serious. Already a formidable player, she entered a period of serious training. She queued up a series of Ken Burns documentaries, bottomless collections of obscure facts if ever there were one. She also played video-game-style trivia games and felt classical music was a blind spot.

“So I listened to a lot of classical music because I didn’t know anything about that,” Caglio said. “I basically went from zero to competent. But I didn’t focus on all of my blind spots. I just tried to get really good at subjects that I was OK at. I did a lot of trying to memorize the elements, and I got a question right about an element abbreviation in one of the games that I played in. I felt really good about that.”

In her finest moment, the Las Vegas Raiders fan nearly ran a category about football penalties, which drew praise from guest host Anderson Cooper and left her feeling “super proud and smug.”

“The penalty category was called ‘Flag on the Play,’” Caglio said. “And when I chose it, I was worried it was a clever name for a category on flags, not a strength, instead of football, a secret strength.”

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Seattle’s Leah Caglio appeared on “Jeopardy!” on Wednesday, April 28. The self-confessed trivia nerd won $17,500.  (Courtesy Jeopardy Productions, Inc.)
Seattle’s Leah Caglio appeared on “Jeopardy!” on Wednesday, April 28. The self-confessed trivia nerd won $17,500. (Courtesy Jeopardy Productions, Inc.)

Caglio was tied with her opponent going into Final Jeopardy and made a substantial bet on the category “Hollywood Legends.” 

She didn’t know the answer, however. So she fell back on her years of experience and did the only thing she could.

“I made an educated guess,” Caglio said.

“It was a really intense game,” she added. “Everybody who was watching, which was just our fellow contestants and the crew, was really amped. It was pretty stressful.”

Faced with the same scenario as Neumann, she also lost in her second game to “a person who was amazing. It was the last game of the day, so I don’t know if she went on to win other games. But I hope that she did because she was great.”

Caglio doesn’t want her fun to end, either, so she and Neumann have opened a roving trivia business called Head in the Clouds.

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“It’s like a pop-up trivia where you can hire us to come to you, and we’ll throw an event in your backyard complete with audio, visual, questions and tactile puzzles,” Neumann said. “My wife’s actually a bartender, so she’ll come along and serve booze to sweeten the deal. We’re also going to host a tournament in the fall.”

Their goal is to make people love trivia the way they do. And maybe start their own “Jeopardy!” dreams.

“We’ve gone to trivia nights every Tuesday since we were 19 — until this past year,” Neumann said. “It’s like our church.”

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