Jeopardy! host Ken Jennings stands alongside four-game winner Rian Robertson on the show's set.

Jeopardy! host Ken Jennings (left) poses with Outlook, Sask., native Rian Robertson, who spent about 15 years trying to get on the show before winning four games. (Jeopardy! Productions Inc./Submitted by Rian Robertson)

Saskatchewan Jeopardy! winner hopes for another shot at glory

By Jacob Bamhour Oct 10, 2026 | 2:02 PM

Four wins, more than US$64,000 — and a chance to do it all again.

After 15 years of trying to get on Jeopardy!, Outlook’s Rian Robertson made the most of his opportunity, winning four straight games before his run ended Wednesday.

Read more:

But the Saskatchewan-raised contestant, who now lives in Ottawa, is hoping he hasn’t answered his final question.

Robertson came up one win short of automatically qualifying for the Tournament of Champions, but says four victories could still earn him another appearance.

“Historically, four is usually enough to get you into the Tournament of Champions,” Robertson said.

There’s also the possibility of returning through a wildcard tournament, although nothing has been confirmed.

“At some point, I will be going back. Well, nothing’s guaranteed in life,” he said, adding that he believes there’s a strong chance he’ll return next year.

Fifteen years in the making

Robertson’s journey to the Jeopardy! stage started about 15 years ago, when he first applied to be a contestant.

Four auditions later, he finally got the call in June.

“There’s obviously a lot of people who are applying every year, so it’s just you got to keep at it,” he said.

Once in Los Angeles, Robertson discovered just how quickly things move behind the scenes.

Five episodes are taped in a single day, giving returning champions only a few minutes to change clothes before playing again.

“Once Ken starts reading the clues, it’s almost like playing sports, right? Where it’s like you’re in game mode,” he said.

Robertson won his first two games before returning for another taping day, where he added two more victories.

Saskatchewan cheering him on

Although Robertson now lives in Ottawa, his Saskatchewan roots got some attention on the show.

He grew up watching Jeopardy! with his father almost every evening before dinner.

“Me and my dad’s thing, we would watch it kind of at 5:30 before dinner, pretty much every night,” he said.

His parents helped rally support back home, and host Ken Jennings even gave Saskatchewan a shoutout during one episode.

As for his US$64,101 in winnings, Robertson says he hasn’t made any big spending plans.

“I haven’t honestly thought about that too much because it was never really about that,” he said. “That was just a nice outcome. It’s more about the experience and playing the game.”

For now, Robertson is waiting to see whether he’ll get another chance behind the buzzer.

“I consider myself lucky that I got to play five games, which is four more games than most people who get on the show get to play,” he said.

And if another opportunity comes along, he’ll be ready.

Read more: