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Portland resident Jason Singer stands at his podium during a taping of 'Jeopardy!' Singer, a former reporter and editor at the Portland Press Herald, will compete on an episode of the trivia show airing Tuesday at 7:30 p.m. (Photo courtesy of Tyler Golden/Sony Pictures Television)
Portland resident Jason Singer stands at his podium during a taping of “Jeopardy!” Singer, a former reporter and editor at the Portland Press Herald, will compete on an episode of the trivia show airing on Tuesday at 7:30 p.m. (Photo courtesy of Tyler Golden/Sony Pictures Television)

Two former Maine journalists have now stood on a soundstage, buzzer in hand, and answered questions for an episode of “Jeopardy!,” the beloved trivia show.

Susan McMillan, a former Kennebec Journal reporter, made her appearance in 2021, winning her first game but losing the second. Now, it’s her husband Jason Singer’s turn. His episode will air on ABC Tuesday at 7:30 p.m.

Singer said he believed that he and McMillan could be the show’s first already-married champions, but other couples have since said they achieved the same accomplishment earlier.

Singer has been a fan of trivia for decades and spent years preparing to be a “Jeopardy!” contestant. But the self-described “wife guy” is perhaps most thrilled by the link he’d have with McMillan if he won.

“I’ve gotten to practice against the Michael Jordan of trivia every day of my life for the last 15 years, and that is an advantage that nobody else in the world has, because I’m the only person who’s lucky enough to be married to Susan,” he said.

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NO TIME TO WASTE

Singer is a former Portland Press Herald reporter and editor who left the newspaper in 2014. Singer said that, like many journalists, he has always been intrigued by facts — down to the finest of details.

“I was always a dork. In elementary school, I would memorize the state and world capitals and the arithmetic tables,” he said. ”

Singer said he and McMillan watch new episodes of the game show every day, a tradition that started shortly after they started dating. Over the years, they’ve created flash cards and an online database for every question they didn’t know the answer to.

Singer was planning to wait until he was older to apply as a contestant so he could hit what he considers his peak level of intelligence.

But in 2019, longtime host Alex Trebek told the world he was diagnosed with pancreatic cancer. Singer and McMillan felt a new urgency and both took the 50-question online test to qualify.

“We weren’t sure if he would survive, if the show would continue and even if the show continued, what form that would take,” Singer said.

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They both got good scores. McMillan heard back immediately, but by the time she was invited on to the show, Trebek had already died. Her episode was hosted by Dr. Mehmet Oz.

Singer, however, didn’t hear back until earlier this year — at which point famed “Jeopardy!” champion Ken Jennings had become the permanent host. In those six years since applying, Singer was still informally training.

Once he got the invite, Singer said, training ramped up until filming day.

GETTING THE INSIDE SCOOP

McMillan, currently an Arabic translator and Army reservist, said there are a few key ingredients to a successful game that viewers at home might not realize from their couches. Singer is currently a real estate agent.

Pressing the buzzer at the exact right time is a fine art. Wagering money in Final Jeopardy, the last round, can take down a contestant who was coasting toward a win. The days are long, and there are often stretches of time between questions.

McMillan helped Singer get his timing down by practicing with a pen, talked strategy on wagering and found a new application for their flash cards.

“The experience I had made him want to prepare even harder, to have no gaps in his game,” McMillan said.

Whether or not Singer wins, McMillan is excited to see him compete. About 100 will gather at a bar in Portland to root Singer on while the episode airs Tuesday.

Editor’s note: This story was updated on July 2 to correct information about whether Jason Singer and Susan McMillan were the first already-married couple to win “Jeopardy!”

Kay Neufeld is a business reporter with the Portland Press Herald, covering labor, unions and Maine's workforce; lobstering, fisheries and the working waterfront. They also love telling stories that illustrate...

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