‘Jeopardy!’ Married Couple Aims to Be Husband & Wife Winners

Jeopardy! fans are in for a treat on Tuesday, July 1, when Jason Singer, from Portland, Maine, competes on the show. He will be hoping to win just like his wife did four years ago, and complete a rare event in the show’s history of a married couple each competing and winning.

Fans will remember how Roger Craig, a 2011 Jeopardy! Tournament of Champions winner, revealed in February that he married Julia Collins, a 20-day champion. He announced their marriage during an episode of the 2025 Jeopardy Invitational Tournament.

In Tuesday’s episode Jason Singer will face off against Heather Kompanek, from New York City, and Monday night’s champion.

His wife, Susan McMillan, a former journalist, won $35,600 during her first game in 2021. She lost her second.

According to the Portland Press Herald, Singer, who used to work for the newspaper, has been a fan of trivia for decades and spent years preparing to be on Jeopardy!. “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 told the outlet.

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

Singer, who works as a real estate agent, and McMillan watch new episodes of Jeopardy! daily, a tradition they started early on in their dating life. The couple created flashcards and an online database for all of the questions they didn’t know.

Singer wanted to wait until he was older to be on Jeopardy!, so he could hit his “peak level of intelligence,” but once Alex Trebek announced his cancer diagnosis, both he and McMillan decided to take the online test.

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

The couple both got good scores, but McMillan, currently an Arabic translator and Army reservist, heard back right away. However, by the time she had filmed her episode, Trebek had already died. Dr. Mehmet Oz was her host during her games. Singer heard back this year and will have Ken Jennings as host, who became the permanent host in 2022. Once he heard back, Singer ramped up his training, which included practicing with a pen, talking strategy on wagering, and a new way to apply their flashcards.

“The experience I had made him want to prepare even harder, to have no gaps in his game,” McMillan said. Singer was not able to be in the audience to cheer his wife on, due to Covid-19 protocols. However, McMillan was in the audience for Singer.

See if Singer wins on Tuesday, July 1. “Some fun history is at stake,” Singer told the Sandusky Register, where he used to work.

Jeopardy!, Weeknights, check local listings