Jason Singer, a Portland real estate agent and two-time "Jeopardy!" winner, returns for the Champions Wildcard tournament, aiming to advance to the Tournament of Champions.

Portland real estate agent Jason Singer, a two-time "Jeopardy!" winner who earned about $50,000 in 2023, is returning to the show for the Champions Wildcard tournament, competing against past champions including Boston College administrator Cameron Berry. Singer, a former Press Herald reporter and husband of fellow champion Susan McMillan, is advocating for his wife’s return, highlighting their rare status as a married couple to win on the show. Inspired by a positive response from producers after a joint "Good Morning America" appearance, Singer is promoting the idea of a family or couples tournament. He has improved his knowledge of current TV shows like "Yellowjackets" since his first appearance. The episode airs Wednesday at 7:30 p.m. on WMTW Channel 8 or streams on Peacock and Hulu. The winner advances to the Tournament of Champions.