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Downtown Toronto CEO Issues Stanley Cup Challenge To Ottawa Tourism CEO

April 24, 2025 by kevinwilkerson Leave a Comment

Toronto Maple Leafs Ottawa Senators
The Toronto Maple Leafs and the Ottawa Senators are in the “battle of Ontario.” Photo: CBC

In a bit of gamesmanship, Downtown Toronto CEO Andrew Weir has issued a Stanley Cup Playoffs challenge to Ottawa Tourism CEO Michael Crockatt.

With the two teams from the respective towns in the playoffs, Weir has made a “bet” to Crockatt in which the CEO of the losing city must travel to the winning city and become its biggest fan for a day. This includes acting as an influencer for the day by promoting local businesses, attractions and the city’s best hidden gems across social media. The Toronto Maple Leafs and the Ottawa Senators are playing in what is locally called “the battle of Ontario.”

“This is a good-natured challenge between two tourism champions who are proud of their cities and passionate about the game,” Weir said. “It reflects what makes Toronto special, we take our sports seriously and know how to host major moments with heart. With our vibrant culture, global connectivity, and proven track record, Toronto’s not only a great destination, but a smart choice for major events.”

There is currently no word from Crockett on his response.

In an amusing twist, Weir issued the challenge on the eve of Game 3. The Leafs are up 2-0, the first time in 23 years the franchise has won the first two games of a playoff series.

As Weir marks his first year as CEO, moments like this show how Destination Toronto is leaning into its identity, bold, collaborative, and proud, and using cultural touchpoints to inspire event planners, investors, and business leaders to think of Toronto first.

Fresh off hosting NHL All-Star Weekend, welcoming the first Canadian NBA and WNBA franchises, attracting high-profile investors like Serena Williams, and hosting the upcoming FIFA World Cup, Toronto is cementing itself as a global hub for sporting events, meetings, and large-scale experiences.

Beyond that, Toronto is one of PubClub.com’s all-time favorite cities to visit. By the way, it’s pronounced “To-ron-o,” not “Tor-on-to.” Not even Al Michaels gets this right. Locals simply call it at “T O.”

This article was written by a human and not AI-generated content.

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Filed Under: Sports Tagged With: Downtown Toronto CEO Offers Stanley Cup Challenge To Ottawa Tourism CEO, NHL Playoffs, Toronto Maple Leafs Ottawa Senators

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