Saskatchewan-born man achieves dream of becoming Jeopardy! champion

Rian Robertson has achieved his longtime dream of appearing on the television show Jeopardy! Robertson, who is originally from Outlook, Sask., had a five game-streak on Jeopardy! winning $66,101 US.

Rian Robertson won a total of $66,101 US from playing on 5 episodes of the show

Emma Stuart-Kiss · CBC News

· Posted: Oct 18, 2026 7:00 AM EDT | Last Updated: 8 hours ago

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A Saskatchewan-born man has achieved a longtime dream of appearing on the television show Jeopardy!

Rian Robertson became a returning champion winning four consecutive games. Across his five appearances he won a cumulative total of $66,101 US.

"I mean obviously as someone who loves the game of Jeopardy!, I wish I could keep playing in perpetuity, but I mean you have got to lose at some point, I guess," said Rian.

The Jeopardy! champion was born and raised in Outlook, Sask., a town located about 80 kilometres south of Saskatoon, with a population of just over 2,300.

He now lives in Ottawa with his wife and four kids, where he spends his days as a software developer at a tech startup that he co-founded. Although he hasn't lived in Outlook for many years, that doesn't mean that his hometown wasn't cheering for him.

"Well, I was kind of lucky because I'm in Ottawa now, so I kind of had two pockets of support, here in Ottawa, but also back home my family, my parents and my sister and old friends were rallying behind me and being my biggest cheerleaders," he said.

"It was just awesome to see the support that was happening back there because I'm obviously from a little small town. So, when someone kind of gets on a big stage like that, it is cool to see everyone rally behind you."

LISTEN | Champion Rian Robertson recalls his time on Jeopardy!:

The 3069:20Outlook, Sask., man finishes five-game Jeopardy! run with $66,101

Rian Robertson, Jeopardy! contestant from Outlook, Sask., joins CBC Saskatchewan's The 306 to talk about his five-game streak and taking home USD 66,101.

From a young age, Rian has been a fan of Jeopardy! He used to watch the show with his father, Ian Robertson, as part of their after school ritual.

While Rian's parents Ian and Susan Robertson were "thrilled" by their son's casting on the show, health issues prevented them from being able to travel to Los Angeles where the show is filmed.

Not being able to attend the show's tapings did not stop the proud parents from celebrating their son's achievements. The couple hosted a viewing party for around 15 people when Rian's first episode of Jeopardy! was aired about a month after it was filmed. Rian tried to convince his mom that he had lost the first episode, but she knew better.

"To be honest, I had my suspicions because I'm quite sure when we told him that we were having friends over to watch, if he hadn't done well, he probably would have said, 'oh, no, no, don't do that.' But he didn't. So I suspected that he won at least one game, but, you know, I wasn't sure," said Susan.

His parents now live a few kilometers down the road from Outlook in Broderick, Sask. They say that the community has been overjoyed by Rian's success.

"I mean, Outlook's not that big, but there are still people I don't know, but they would stop me on the street and congratulate me, to pass it on to him," said Susan.

A big step toward a lifelong dream

For Rian, making it on the show was a dream years in the making. He says that he's been trying to get on the show seriously for about 15 years, but his interest in facts and general knowledge questions can be traced further back to childhood.

His father remembers when he started curating his own collection of fascinating facts.

WATCH | Rian Robertson talks about his win streak on Jeopardy!:

Sask. Jeopardy! contestant wins $66,101 on five-day streak

October 14|

Duration

3:45

From Outlook, Sask. to Los Angeles. Rian Johnson joined The 306 to talk about his successful run on Jeopardy!

"When he was younger, whenever he found out a fact that he kind of liked or was interested in, he would write it in this loose leaf paper and stick it in a binder. And he called it his book of knowledge," said Ian.

Rian's wife Kristina Robertson also knew from their first meeting that Rian was a whiz with general knowledge. The couple met at a trivia night, although Kristina says that trivia is very much Rian's domain in their marriage.

Kristina was able to watch the filming of two of her husband's Jeopardy! episodes, including his nail-biting second episode where he came from behind to win. She knows that for her husband being on Jeopardy! is a stepping stone to achieving his bigger dream.

"Rian's goal, yes, it was to get on Jeopardy!, but ultimately his goal is to win that Tournament of Champions," said Kristina.

"You know half of his dream has come true, put it that way."

Jeopardy! champion Rian Robertson stands smiling behind his podium. (Submitted by Rian Robertson)

But back in Broderick, Rian's quest to achieve his dreams has already changed at least one life.

"I am just so thrilled, because I mean to see anyone achieve a lifelong dream is amazing, and in fact, he's inspired me to get back on the bandwagon because my dream is to be fluently bilingual in French before I die," said Susan.

"Maybe that's not the best way to put it, but since he was on Jeopardy!, I've taken back up on my lessons in French. So he's an inspiration to his mother."

ABOUT THE AUTHOR

Emma Stuart-Kiss is a reporter based in North Battleford, Sask. Have a story idea? She can be reached at emma.stuart-kiss@cbc.ca