The chants, cheers and jeers of over 100 people filled a wing of Brickyard Hollow Brewing Company in Portland on Tuesday night. The competition on the big flat-screen TV in front of them was “nerve-wracking,” and the atmosphere was “electric,” attendees said.
But it wasn’t one of New England’s sports teams on the big screen. It was Portland’s Jason Singer taking to the “Jeopardy!” stage — and winning.

“This was louder than any Super Bowl party or World Series party I’ve ever been to,” Singer said in an interview after the watch party at Brickyard Hollow, with friends and family giving him pats on the back as they trickled out. “I feel very fortunate to have so many wonderful people in my life.”
Singer, a former reporter and editor for the Portland Press Herald, and his wife, Susan McMillan, a former Kennebec Journal reporter, said they believed that they were the first couple to win “Jeopardy!” while married to each other. However, other married couples have since said they already achieved the same accomplishment.
“It’s anecdotal. ‘Jeopardy!’ doesn’t track every married couple that’s ever been on, but they’ve written about a bunch on their website,” Singer said. “Whether we’re the first, the second or the first in a long time, I just think it’s a really cool accomplishment.”
When the “Jeopardy!” theme music hit at 7:30 p.m., the room rumbled with anticipation. Singer’s introduction, and each time he answered correctly (he got 25 out of 30), was met with applause, hoots and hollers.
As for his opponents, they got New England’s classic New York Yankees treatment.
But it wasn’t an easy win by any means. At the first commercial break, Singer was in last place. Same by the second commercial break, which concluded the first round.
There were two instances when Singer answered correctly, but just after his time expired. Spectators booed. One called for a video review.

Little did they know, off-air, they got their wish.
“They paused the game for a couple of minutes on each of those misses to see if I got it in time,” Singer said. “Both times I knew in my heart I didn’t, so I was on stage for five or 10 minutes just stewing.”
Singer was down.
“It was a hard pill to swallow. You lose, you go home,” he said. “This is your only chance in life of being a “Jeopardy!” champion. If you lose, you don’t get to go back.”

But Singer thrived in the second round, answering two “very hard” daily doubles.
“‘Edward Hopper’ and ‘Meet the Press,'” Singer recounted. “I felt fortunate to be able to get them and give myself a little breathing room, but I still needed to get the Final Jeopardy.”
Heading into Final Jeopardy, Singer was ahead with $17,800 while his two opponents had $11,200 and $6,000 respectively.
The final clue?: “In 1991, he became the first actor in over 85 years to be interred in Poets Corner and rests near Shakespeare’s memorial.”
Singer was the last contestant to reveal a response, “Who is Laurence Olivier?” and wager, $4,601. The correct answer made him the winner, with $22,401.
A chant of “JA-SON! JA-SON!” slowly caught on until the room was full of it, but that soon turned to chants of “SU-SAN! SU-SAN!”
“It was nerve-wracking,” said friend Blaise MacDonald. “I’ve been in college athletics for 40 years and I was nervous, excited and so happy. It was an honor to be here.”

MacDonald said he golfs with Singer and has always admired his “curiosity and sportsmanship,” and said “he’s just a good human being.”
Peter Lyons said he runs and walks with Singer and McMillan three days a week.
“It’s nice to see him successful on a whole other stage,” he said, “and it was so much fun to see Susan win in 2021.”
Kelsey Freedman, a family friend, said Singer is “such a well-rounded individual” and that it likely contributed to his success on “Jeopardy!”
“It was awesome,” Freedman said. “It was great to be able to cheer him on.”
McMillan said it was “a wonderful turnout” and that she’s grateful so many people came to support her husband.
“Jason gave us a very exciting show to watch,” she said. “It didn’t look very good there for a while, but it was exciting to see him pull it out in the end, and the energy from the audience here was amazing.”
Ahead of McMillan’s and Singer’s respective “Jeopardy!” appearances, they helped each other prepare.
“We started creating flashcards, even before I went on the show four years ago,” she said. “We always knew Jason was going to try someday, so even after I was on the show, we just kept making flashcards and never really stopped.”
Singer said his win was a team effort.
“We do everything as a team,” he said. “We do the New York Times crossword puzzle every night as a team, we plan trips as a team, we cook as a team. It’s nice to share this honor with her.”
The couple’s goal is to get McMillan back on “Jeopardy!” An opportunity for her return, the Wild Card Champions Tournament, reserved for contestants who “win dominantly,” didn’t exist when she was on in 2021, Singer said.

McMillan won $35,600 in her debut.
“She’s as dominant a one-day champion they’ve ever had,” Singer said. “She is brilliant and beautiful and funny — why wouldn’t anybody want her on television again?”
Singer gave in to a “Speech! Speech!” chant after the show aired. He said he has been sober for five years (which was greeted with applause) and having so many people he cares about there to support him on Tuesday meant a lot.
“I was an addict for a long time, I haven’t had as smooth a ride as some people,” he said. “I lost a lot of years in terms of studying and just becoming a more well-rounded person, but I put in enough time to get enough ‘rights’ and I’m thankful for that.”
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!”
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