Calgary man takes on greatest Jeopardy player ever. Guess the ending

Jeff Henderson was determined to make it onto Jeopardy before Alec Trebek stopped hosting the show. Then James Holzhauer happened.

Playing James Holzhauer felt like being one of the soldiers in the opening scene of Saving Private Ryan

Jeopardy host Alex Trebek with Calgarian Jeff Henderson, who was a contestant on the show against James Holzhauer, who has won 22 straight and over $1.6 million (Jeopardy Productions)

Calgarian Jeff Henderson had to answer a lot of questions, about plenty of topics, to make it all the way onto the set of Jeopardy, and he managed to do that.

During a commercial break while they were taping, host Alex Trebek  tried to make small talk in the only way two Canadians in Los Angeles usually can.

"Alex tried to start a conversation with me about hockey and he picked the wrong Canadian," said Henderson. "I'm the one Canadian who can't answer anything about hockey. So he was like, how do you think the Leafs will do this year? [And I was like] I'm so sorry to disappoint you Alex Trebek."

Despite giving the wrong answer to Trebek's attempts at making Canadian small talk, Henderson gave enough correct answers when it mattered — during the audition — to get invited to appear on the popular game show, which has been in the news lately thanks to the amazing 22 game winning streak of professional gambler James Holzhauer.

Henderson's own experience to getting on the show was a story of perseverance.

"I never was one of those like in-a-trivia-league-in-high-school kind of people," Henderson said. "I used to watch the show and get maybe five answers right per show. Then I decided I wanted to study to get on the show one day before Alex left," he added, in a Thursday interview on The Homestretch.

"I learned some U.S. presidents, knowing that probably my Canadian education wouldn't be enough there for the U.S. president knowledge," he said, "and some other things as well and I studied enough to be able to pass the test to get on the show."

James Holzhauer on April 17, 2019. On his 14th appearance on Tuesday, April 23, 2019, Holzhauer eclipsed the $1 million mark in winnings. (Jeopardy Productions, Inc./Associated Press)


Unfortunately for Henderson, he got on the show right in the middle of the run of Holzhauer, a professional gambler who very well may be the greatest Jeopardy player of all time.

Unlike Henderson, Holzhauer likely didn't have to study up on his American presidents to make it onto the show, Henderson said.

"Apparently he was featured in The Chicago Tribune when he was four years old for being a math prodigy," he said.

Jeff Henderson studied up on American presidents in order to take the test to become a guest on Jeopardy. (Ellis Choe/CBC)

Henderson's approach to going on the program was to focus on being better on the buzzer than any other guest.

"I'd bought this book on the buzzer. I knew the optimal way to to hold the buzzer," he said. "There's books written about it. And I had a practice one.

"It turns out James had read the same book and had a lot more practice with the actual buzzer. And it turns out a lot more knowledge than me as well."

During his taping session, five episodes were taped.  That's where Henderson got an up-close-and-personal, firsthand experience of witnessing Jeopardy greatness.

"He beat the highest score of all time to set the record — and didn't just kind of beat that record," he said. "He shattered it.

"The previous record with 77,000 had been there for a decade — and he went and got 110,000."

'They called my name'

'People were losing their minds," Henderson said. "I've never seen anything like this. And then they called my name.

"It's your turn to go up!"

So what was it like to be sitting in the players pool, watching Holzhauer destroy every Jeopardy record, knowing you could be next?

"We felt like the soldiers in the opening scene of Saving Private Ryan, just shaking in our boots knowing what was coming," he said.

"It also was just incredible to be in awe of what I'm witnessing," he said, "while also being destroyed by it."

Holzhauer is still on the show, having won $1.6 million and counting.

How did Henderson do?

"I owe Alex Trebek $600," Henderson said.  "He's got to come to Calgary to collect."

With files from The Homestretch


Stephen Hunt

Digital Writer

Stephen Hunt is a digital writer at the CBC in Calgary. Email:

With files from Ariel Fournier


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