Jason Singer said it was “one of the most frustrating experiences” of his life: The answers were on the tip of his tongue, but his timing was off by milliseconds.
The Portland resident and two-time “Jeopardy!” champion took to the game show stage again for the taping of Wednesday night’s episode. After winning twice this summer, the real estate agent and former Portland Press Herald reporter was invited back to participate in the Champions’ Wild Card, a tournament for winners who did not qualify for the show’s Tournament of Champions.
Singer, 39, answered correctly on the very first clue, but didn’t get a chance to provide another before the first commercial break. Over the course of the game, Singer reckons he pressed the button at least 40 times, but his podium only lit up on 13 occasions.
“I kept telling myself, ‘You know all the answers. You’ll be fine. Just stay patient,’” Singer said following the airing of Wednesday night’s episode, which was taped in advance. “But the deeper we got into the game, the more frustrated I became.”
He had better timing coming out of the first break and in Double Jeopardy!, but his opponents kept narrowly beating him to the button every time he seemed to be getting into a rhythm.
Entering Final Jeopardy!, Singer trailed the leader by over $9,000. He had no choice but to go all in, wagering all of his $3,900.
None of the contestants answered correctly, but contestant Harvey Silikovitz pulled out the win, wagering only $2 and narrowly defeating fellow contestant Cameron Berry.
Singer applauded his opponents for being “a step faster than me all night,” and said he’d be rooting for them in the semifinals
The loss stings, Singer said, but he couldn’t be happier — or more proud — to have gotten the chance in the first place. Singer was an addict for over 20 years, he said, but has been sober for more than five years.
“I’m thankful to be on a track where I’m bettering myself day after day,” he said. “I could’ve never done this six or seven or 10 years ago.”
Singer previously appeared on three “Jeopardy!” episodes in July, winning two games and about $50,000. As he did in his first three appearances on the game show, Singer included “#BringBackSusan” alongside his Final Jeopardy! answer and wager in Wednesday night’s episode.
Singer’s wife, Susan McMillan, took home $35,600 in her sole victory in 2021. The two are part of a very small group of couples who have both won on the game show.
“She’s significantly better than me,” Singer told the Press Herald earlier this week. “She’s a super champion in waiting.”
Beyond the thrill of competing on Jeopardy!, Singer said he appreciates the support and enthusiasm from loved ones and the Portland community at large.
“I love my friends, I love my family and I love this city,” he said. “I’m excited to have given everyone something small to cheer for and rally around.”
