JANUARY 11, 2025

Dear reader,

The first time Donald Trump joked about making Canada the “51st state,” politicians north of the border scoffed. This week, when the president-elect doubled down on the proposal in response to Prime Minister Justin Trudeau’s resignation—and a looming trade war—no one was laughing. In a baffling turn of events, some prominent Canadians went so far as to support the idea: Kevin O’Leary, who was wining-and-dining at Mar-a-Lago just last weekend, claimed to find the suggestion of a US–Canada merger “very interesting.”

O’Leary is no stranger to punchy, headline-grabbing statements. And much like Trump, he’s been known to follow through on claims that would be easy to dismiss as trolling. In 2016, Toronto Life writer Jason McBride profiled the business mogul as he toyed with the idea of running for the leadership of the Conservative Party of Canada. At the time, O’Leary spoke about the possibility with a Trumpian irreverence toward democratic institutions: “I don’t give a damn about the party,” he said. “They’re losers.” Then he tried—and failed—to lead them.

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—Madi Haslam, digital editor

The dastardly reality TV star’s flirtation with a federal leadership bid is sending the Conservative party into convulsions. There’s never been a better time to be an opinionated blowhard in politics, but is Canada really ready for Prime Minister O’Leary?

BY JASON MCBRIDE | AUGUST 24, 2016

Kevin O’Leary is Canada’s most famous businessman and one of the country’s most successful television exports. It’s difficult to tell where one role ends and the other begins. O’Leary has monetized his entire existence into a cunning hustle: as the loud-mouthed dark lord of Shark Tank, he can promote his own products and services while ferreting out new ones to profit from. In 2016, as O’Leary continued to pontificate on financial matters, he turned his attention, loudly, to politics, announcing that he might run for leader of the Conservative Party of Canada. The will-he-or-won’t-he (spoiler alert: he did) was a long, slow, sadistic tease—one that O’Leary relished. 

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