3 min read
Jason Singer and his wife, Susan McMillan, at a watch party in July for a "Jeopardy" episode Singer won. McMillan is also a past "Jeopardy" winner. (Daryn Slover/Staff Photographer)

Jason Singer will get another chance to showcase his talent for trivia when he makes a return visit to “Jeopardy!” on Wednesday night as part of a champions’ tournament.

The Portland real estate agent is also using the moment to continue lobbying for his wife —  fellow “Jeopardy!” champion Susan McMillan —  to be invited back onto the show.

“She’s significantly better than me,” said Singer, 39, on Monday. “She’s a super champion in waiting.”

Singer will be competing Wednesday as part of the show’s Champions Wildcard tournament, one of several tournaments for past winners. Singer previously appeared on three “Jeopardy!” episodes in July, winning two games and about $50,000. Those wins let him and McMillan join a very small group of couples who have both won on the game show. McMillan won one game, and $36,500, on the show in 2021.

Jason Singer poses with host Ken Jennings during Singer’s first appearance on “Jeopardy!” (Courtesy of Tyler Golden/Sony Pictures Television)

Singer, who worked as a Press Herald reporter and editor from 2011 to 2014, was invited to this week’s champions’ tournament based on his two wins, his scores and the quality of his opponents. But when McMillan was on “Jeopardy!”, this tournament didn’t exist, so Singer thinks she deserves a comeback appearance too. McMillan is also a former Maine journalist, having worked as a reporter at the Kennebec Journal.

After he won in July, Singer and McMillan appeared on ABC’s “Good Morning America,” talking about their “Jeopardy!” experiences as a married couple. Singer, who uses the hashtag #BringBackSusan on his social media posts, said “Jeopardy!” producers heard that interview and were intrigued by the idea of a couples or family tournament. Singer says it’s more likely the show will consider a family tournament, with siblings and parents as well as couples, so he’s planning to go on social media this week to ask fans to support that idea.

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“There are so many reality shows focusing on family stresses and there are so many game shows,” said Singer. “So it would be great to combine the two.”

Wednesday’s episode of “Jeopardy!” can be seen at 7:30 p.m. on Portland station WMTW (Channel 8), or streaming on Peacock and Hulu. One of Singer’s two competitors Wednesday will be a native Mainer, Cameron Berry, who spent the first seven years of his life in Falmouth and has strong family ties to the area.

Berry, 32, works as an administrator at Boston College, but says he’s trying to arrange a viewing party in Falmouth for family members. When he was on the show in March, winning one game, he had a viewing party in the Boston area for friends and colleagues.

Singer and Berry are friends and have already competed against one another in online “Jeopardy!” games for past and future contestants. In those games among past champions, Berry said Monday, it’s clear that “anyone can win.” The winner of the Champions Wildcard tournament will advance to the show’s annual Tournament of Champions.

When Singer was on the show in July, more than 100 people jammed a watch party for him at Brickyard Hollow Brewing Company in Portland. But on Wednesday, Singer and McMillan will be out of town and won’t be able to duplicate that experience.

Family and friends of Jason Singer celebrate at Brickyard Hollow Brewing Company in Portland after Singer won on “Jeopardy!” in July. (Daryn Slover/Staff Photographer)

Singer said he learned a few things from his first time on “Jeopardy!,” including that he needed to be more knowledgable about current hit TV shows, after missing a clue about the Showtime thriller series “Yellowjackets.” So before heading out to Hollywood for his most recent “Jeopardy!” filming in November, he read up on the top shows, what they are about and who the stars are.

He also realized that his nerves and lack of sleep during his first appearance probably hurt him. He says he only got two or three hours of sleep before that first filming session and wasn’t as sharp or as quick as he could have been.

So when he traveled to the show this last time, he arrived in town several days early to get more rest and get his body in rhythm. He also brought his wife, since she wasn’t able to accompany him the first time. They’ve been married for 15 years and together for 20.

“I had less nerves this time, Susan being there helped,” Singer said.

Ray Routhier has written about pop culture, movies, TV, music and lifestyle trends for the Portland Press Herald since 1993. He is continually fascinated with stories that show the unique character of...

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