What to know about Kevin O’Leary as he weights into U.S. politics

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Canadian businessman Kevin O’Leary has been weighing in on U.S. politics, as tensions between the neighbouring countries continue to rise amid an ongoing trade war.

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The 70-year-old from Montreal made recent appearances on American news outlet CNN as a panel contributor, as well as on a podcast and in the Washington Post, musing about closer ties between the countries. He has raised ire among many Canadians for comments that seem pro-American to people anxious over Trump’s threats.

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O’Leary has been a public figure in the spotlight in Canada and the U.S. since he appeared as a host — or a “shark” — on the business reality television series Shark Tank in 2009, and its Canadian predecessor Dragon’s Den in 2006. That’s where he created his television persona as a blunt, straight shooter, with the nickname Mr. Wonderful.

Decades later, he is still in the spotlight, quipping about Canada and U.S. relations and sharing his views online. O’Leary is an author, winemaker, guitar collector (and player) and has a passion for photography. He currently runs private venture capital investment company O’Leary Ventures.

Here’s what to know about O’Leary.

What is Kevin O’Leary saying about the U.S. and Canada?

In an episode of finance podcast The Daniela Cambone Show posted online on Monday, O’Leary criticized Mark Carney, the newly elected leader of the Liberal Party and current prime minister. O’Leary said his policies would harm Canada. He also spoke about U.S. President Donald Trump.

“Trump can’t stop with the ‘Let’s buy Canada’ and ‘make (it) the 51st state.’ That’s just his nature, but you’ve got to differentiate the signal from the noise,” he said. “The next step into the journey into the negotiations with the U.S. is the Canadian election.”

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In a post on X with a clip of his interview, he said that “Canada’s economy is at a turning point” and asked, “but who’s leading?”

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“Premiers are scrambling, flying to Texas, Washington — doing deals on their own. That’s not how you negotiate trade. We need a federal mandate. Canada’s not for sale, but the opportunity for economic alignment with the US is massive — if we don’t screw it up,” he wrote.

He also said he didn’t “buy” the fact that Trump truly wanted to annex Canada, in reference to comments made about the country becoming the 51st state. He called Trump “bombastic” and “outrageous.”

“It’s the hangover effect of how much he hated (former Prime Minister Justin) Trudeau,” said O’Leary.

In a Washington Post article published on Thursday, the links between O’Leary and Trump were highlighted. Both have made the case for uniting the countries — although O’Leary suggested a “formal economic alliance…similar to the European Union,” per the publication, rather than Trump’s annexation threats.

“China is the problem right now, and it’s going to remain so as it tries to become the world’s largest economy,” said O’Leary, the Washington Post reported. “If somehow we combine the economies of Canada and the United States – game over. It’s over. Nobody could touch us.”

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When he spoke with Trump in January at Mar-a-Lago, O’Leary brought up the subject of Canada, which could have pushed the president to think more deeply about it, per the Washington Post.

“I don’t know if it was something I said that got him thinking about that,” O’Leary. “And that was the beginning of something. But I can’t claim that I gave him the idea. Who knows? I have no idea.”

What is O’Leary’s connection to Trump?

O’Leary backed a second Trump presidency, publicly declaring his support on news outlets such as Fox News and CNN, the Palm Beach Post reported in December. He flew to Mar-a-Lago, Trump’s Florida estate, in January and attended the president’s inauguration in Washington, D.C.

“This wasn’t your typical speech full of historic throwbacks,” wrote O’Leary in a post on X. “It was direct, action-packed, and all about what’s happening now.”

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What about his own political aspirations?

In January 2017, O’Leary announced that he would be running for leadership of the Conservative Party of Canada.

“I am a successful Canadian businessman with a great deal of international experience. I have seen first-hand Trudeau’s gross economic mismanagement, and the effect it is having on our country. Many Canadians were optimistic when Trudeau promised them he would balance the budget by 2019. That is not what happened,” he said in a post on his website. “I have spent a lifetime fighting on behalf of investors, but the outcome of the next election is too important to the future of our country. I have had enough of Trudeau’s mismanagement, so I have decided to fight for all Canadians.”

Three months later, he dropped out of the race. At a news conference in Toronto, he said, per the National Post, “It’s selfish to just take the leadership and say, ‘Great, I’m the leader, now in 24 months I will lose for the party. That’s not right. That’s just wrong.”

Why were the O’Learys in the news a few years ago?

In the summer of 2019, O’Leary and his wife Linda, were involved in a boat crash that left two dead in Ontario’s cottage country. The incident occurred at night time, with O’Leary’s wife as the driver, when the two boats collided. A judge ruled in 2021 that Linda was not “guilty of operating a vessel in a careless manner,” the National Post reported.

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How did O’Leary get his start?

O’Leary attended the University of Waterloo, where he received an Honours Bachelors degree Environmental Studies and Psychology in 1977. He then attended the Ivey Business School at Western University. He received his Masters in Business Administration in 1980, according to an archived Ivey webpage.

While he was earning his MBA, O’Leary interned at snack manufacturer Nabisco, per his bio on his website. He was one of the founders of Softkey in 1986, when he collaborated “in a basement with his business partners,” his bio says. In 1999, SoftKey, which later acquired The Learning Company and took its name, was purchased by toy company Mattel for $4.2 billion.

He also hosted CBC business show The Lang and O’Leary Exchange.

In an interview with Boston Magazine, he said his nickname Mr. Wonderful was coined by fellow “shark” and entrepreneur Barbara Corcoran, who jokingly called him Mr. Wonderful after he “proposed an aggressive 51 percent equity position (on a deal) because (he) wanted control of the business.”

“Now it’s at a whole new level,” he said in the 2013 interview. “I show up at hotels and my reservation is under the name Mr. Wonderful. They don’t even know my real name. That’s just nuts.”

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