A six-time Emmy Award winner, Jeopardy! host Alex Trebek has been a beloved fixture in North American pop culture since the game show’s pilot episode aired in 1984. But success wasn’t always a sure thing for Trebek—or these people who made the most money on Jeopardy!.
The Sudbury, Ont. native bounced around the broadcasting circuit for years before he landed Jeopardy!, and it wasn’t quite the straightforward arrival you’d imagine. Starting out on the Canadian airwaves, Trebek transitioned from the radio to Canadian sports to the American game show circuit. There, he took several gigs throughout the ’70s, including High Rollers, Double Dare, and The $128,000 Question, but none of them really took.
Trebek eventually began hosting Pitfall, a Canadian game show that showcased contestants attempting to cross an eight section bridge in 100 seconds by answering questions, avoiding “pitfalls” along the way. The show’s title should have been a harbinger for Trebek, as Pitfall’s packager, Catalena Productions, went bankrupt in 1982 just a year after he was hired. A $49,200 cheque that Catalena Productions wrote Trebek bounced. To this day, he hasn’t seen a dime.
“It came at a bad time because my father had died and I was in bad, bad straits and could have used the money,” said Trebek in David Baber’s Television Game Show Hosts: Biographies of 32 Stars. “Interestingly, in a career that spans 45 years, the only time I’ve been done that way was by fellow Canadians. Fellow Canadians shafted me.”
Just two years later, Trebek began hosting another fledgling trivia game show: Jeopardy!. In its second season, the show was paired with Wheel of Fortune (which Trebek also spent a brief period hosting in 1980 when Chuck Woolery fell ill for a week) and aired during a more desirable time slot. With the proper grooming, Jeopardy! bloomed into the colossal hit we all know today, and only a year after airing became the second most-watched syndicated series in the country.
The $49,200 cheque from Pitfall still hangs in Trebek’s home, framed.