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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 during a taping of “Jeopardy!” Singer, a former reporter and editor at the Portland Press Herald, won two episodes on the famed quiz show before coming up short in his third show, which aired Thursday night. (Courtesy of Tyler Golden/Sony Pictures Television)

After a comeback win Tuesday and using an all-in wager to secure a second victory Wednesday, Jason Singer, of Portland, saw his run on “Jeopardy!” come to an end Thursday night.

“This one is tough to swallow,” Singer told the Portland Press Herald.

In his third show, Singer built a comfortable lead in the Double Jeopardy round but tripped up on a Daily Double, opening the door for his opponents to get back in the game.

He still carried a slim lead into Final Jeopardy, but his response was incorrect.

“I had two chances to put it away and couldn’t come up with ‘The Fabelmans’ or ‘Yellowjackets,’ two properties I’m very familiar with,” he said.

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Singer said his time on “Jeopardy!” was “the thrill of a lifetime,” even though it was full of ups and downs.

“I had a lot of trouble sleeping the week of the tapings. Nerves are 100% real,” he said. “My brain wasn’t working as well as it should’ve been.”

But he gave a tip of the hat to Thursday night’s winner, Scott Riccardi.

“Scott is a phenomenal player and deserved the win,” Singer said.

Jason Singer and his wife, Susan McMillan, back center, celebrate during a “Jeopardy!” watch party at Brickyard Hollow Brewing Co. in Portland on Tuesday. Singer won Tuesday and Wednesday night’s episodes before a wrong answer in Thursday’s Final Jeopardy round ended his run on the famed quiz program. (Daryn Slover/Staff Photographer)

On Tuesday night, Singer joined his wife, Susan McMillan, as a winner of the ABC game show. That was celebrated at a watch party at Brickyard Hollow in Portland, where over 100 people cheered on his comeback win, in which he took home $22,401.

His second victory on Wednesday was a nail-biter. Entering Final Jeopardy, Singer was tied with opponent Jeff Foels at $13,200. Both responded correctly, but while Foels wagered just $3,599, Singer risked his entire pool and wound up walking off the stage with $26,400.

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Singer has been advocating for McMillan to go back on the show. She took home $35,600 in her sole victory back in 2021. He’s even included “#BringBackSusan” on all three of his Final Jeopardy responses.

“I truly hope ‘Jeopardy!’ brings my wife back, both for the Jeopardy Invitational Tournament later this year, and hopefully a couples tournament down the road,” Singer said. “She was great four years ago when she was a dominant champion, but it’s hard to properly describe how good she has become in the last four years.”

While his run came to an end on Thursday night’s episode, Singer hopes to be invited back for the Champions Wildcard Tournament later this year.

“I’m forever grateful to ‘Jeopardy!’ for giving me this wonderful experience and for all my friends and family and show-watchers all around the world who have given me so much love and support this week,” Singer said.

Portland resident Jason Singer poses with host Ken Jennings during a taping of “Jeopardy!” (Courtesy of Tyler Golden/Sony Pictures Television)

As for his roughly $50,000 in winnings, Singer said he and McMillan will be going on a trip to Japan this fall to celebrate McMillan’s 40th birthday and their 20th marriage anniversary.

“Losing like this is pretty painful,” Singer said, “but traveling with Susan and eating good sushi tends to heal all wounds.”

Drew is the night reporter for the Portland Press Herald. He previously covered South Portland, Scarborough and Cape Elizabeth for the Sentry, Leader and Southern Forecaster. Though he is from Massachusetts,...

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