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John Levy seemed so confident – but then, that’s his default setting. It was the fall of 2019, a couple of months after he had successfully orchestrated the launch of his company’s new sportsbook, theScore Bet, in the United States, and he was predicting big things. “I don’t see any reason why, over time, we can’t own 10 per cent of [the U.S. sports-betting] market,” he told The Globe and Mail in an interview. “Three years from now, if we’re not one of the top players, I’d be very surprised.”

Levy was preparing to go up against sportsbooks backed by glitzy brands and multimillion-dollar ad campaigns, but theScore had developed a user base of millions for its mobile sports-news app by being smart and nimble, just as it had attracted a loyal following for its upstart sports-news TV channel back in the day. “I think, over time, we’re going to beat the heck out of them, regardless of how much they spend,” he boasted.

It didn’t quite work out that way, though Levy did receive a pricey consolation prize.

In the fall of 2021, Penn National Gaming Inc. snapped up theScore for US$2-billion. Today, the app is leading something of a double life. It is on its way to becoming bigger than Levy could have imagined, even though its name is nowhere to be found any more on the U.S. sports-betting landscape. And its fate may be a cautionary tale for Canadian companies that believe they can conquer America.

A few weeks ago, Penn announced that Levy would step down as executive chairman of theScore this month. In April, his three sons will follow him out the door: Benjie, who serves as head of Penn Interactive and president and COO of theScore; Aubrey, senior vice-president of marketing and content; and Noah, senior vice-president of product management at theScore.

Levy père occupies a special place in the hearts of sports fans in Canada, as one of the few remaining original cable cowboys who knew the value of showmanship and independence. In the mid-1990s, having taken over his father’s cable company, the Hamilton-based Western Co-Axial, he launched a sports-ticker service on TV that gave fans easy access to news when their only real alternative was dial-up Internet. Levy acquired a TV licence, sold the cable company, and launched Headline Sports, a sports-news channel, which was eventually rebranded as The Score.

That operation was a bare-bones affair that carved out a niche in the long shadow of TSN and Sportsnet. With little money for live sports rights, it focused instead on developing on-air talent and a scrappy, elbows-up attitude. Its deep bench included Elliotte Friedman, Brendan Dunlop, and soccer broadcasters Greg Sansone, James Sharman and Kristian Jack. It’s where Tim Micallef and Sid Seixeiro first shared an anchor desk.

In 2012, Rogers Media bought the channel for $172-million, renamed it Sportsnet 360 and, in the way of such things, stripped it of its unique personality. Nowadays, Sportsnet 360 airs a mixed bag of UFC and WWE programs, U.S.-based sports-betting programs, hockey reruns and other stuff that spills over from the main Sportsnet channels, and simulcasts of Sportsnet Radio’s talk shows.

With the cash from the sale, Levy pivoted to the next big thing. As part of the deal, he held onto The Score’s digital assets, building out its nascent sports-news app and waiting for sports betting to be legalized in the United States. When that finally happened, in 2018, theScore had millions of regular users they aimed to convert into sports bettors, leveraging the base into a position of market dominance.

The market had other ideas. Because it turns out that even millions of users don’t count for much when you’re going up against tens of millions of marketing dollars.

In June, 2022, only eight months after it acquired the company, Penn shut down theScore Bet in the United States (even as the sportsbook had just launched in Ontario). Instead, having acquired a minority stake in the digital-media company Barstool Sports in 2020, Penn decided to go all-in on that frat-house-flavoured brand. Early last year, it bought the rest of Barstool and migrated its sportsbook app over to theScore Bet’s superior back-end technology platform: all the boring guts of the operation that nobody notices but actually help make the user experience pleasurable.

But sometimes wagers that seem like sure things explode in a bettor’s face. Since its launch 20 years ago, Barstool has amassed a zealous fan base with an attitude and content that was notoriously divisive. Its freewheeling approach didn’t marry well to the restrictions of a highly regulated activity such as sports gambling. And so, only seven months after it had bought up the rest of Barstool – for a total outlay of more than US$550-million – Penn sold it right back to the company’s founder, for US$1, and replaced it with a safer bet that comes with a global brand – a US$1.5-billion, 10-year deal with ESPN to operate a sportsbook in that company’s name, ESPN Bet.

And yes, that sportsbook was built on top of theScore Bet’s unsexy tech platform. Which is, in many ways, a sadly familiar story for Canadian businesses. Throughout its history, this country has been a place of great natural bounty, providing the raw materials that foreign companies have transformed into products and services for great profit. Over the past couple of decades, that extractive model has moved into the business of intellectual property. Toronto and Vancouver are home to extremely busy TV and film production hubs that keep workers busy pumping out shows for U.S. producers to sell to the world.

Back in Toronto, at the headquarters of theScore, workers are still supporting the app and trying to grow the company’s sportsbook business in Canada. But its American dream is officially dead, and the Levy family are about to ride off into the sunset. In that interview with The Globe in 2019, Levy, who was 66 at the time, was asked how long he expected to keep going. He scoffed at the question. “I’m just having too much fun,” he replied. “There’s no limits on this thing.” And yet there were.

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