Kevin O'Leary tells well-heeled Conservatives in Florida he'll enter leadership race

Undeclared Conservative leadership candidate Kevin O'Leary recently met with a group of wealthy Canadians in Florida to discuss a possible bid and told them he could enter the race as early as Jan. 19, CBC News has learned.

Businessman and television personality could enter leadership race as early as next week

Businessman Kevin O'Leary, a former panelist on CBC's Dragons' Den, is considering a run for the Tory leadership. (CBC)

Kevin O'Leary told a group of wealthy Canadians wintering in Florida last week that he will run for the Conservative leadership and enter the race as early as Jan. 19, CBC News has learned.

The businessman and television personality denied suggesting such a date during an interview on CBC's Power & Politics Monday, but acknowledged a meeting took place while he was in Florida on business.

"I'm meeting with anybody that wants to talk about Canada. As you know, down in Florida, this time of the year, there's a lot of Canadians there, so it's easy to get a quorum. And we talked a lot about what's going to happen to the country on its current path," he said.

"I never asked them for money. I just asked them to listen to some ideas."

Multiple sources who requested they not be identified because they weren't authorized to speak publicly told CBC News the exploratory committee advising O'Leary will provide him with an assessment of his candidacy and a possible path to victory this week.

'Please tell me when we're down to, say, four or five' candidates, O'Leary says. 11:20

That committee includes former Ontario premier Mike Harris and Mike Coates, who helped Stephen Harper prepare for election debates in 2004, 2006 and 2008.

French tutor

The report will include recommendations for possible launch dates for his candidacy. One of those dates is Jan. 19, the day before Donald Trump will be inaugurated president of the United States.

According to sources, O'Leary is working with a French tutor and will commit to becoming bilingual.

But he seems unlikely to enter the race before next week's leadership debate in Quebec City, an event that will be conducted entirely in French.

Candidate Andrew Scheer has challenged O'Leary to participate in that debate.

Conservative leadership contender Andrew Scheer wants O'Leary to participate in next week's leadership debate in Quebec City. (Adrian Wyld/Canadian Press)

Speaking with Power & Politics, O'Leary said the leadership field of 14 candidates is still too crowded for a proper debate.

"You tell me when the herd will be culled ... and I'll tell you when I'm joining," he said. "Please tell me when we're down to, let's say, four or five. Then we'll talk turkey."

But O'Leary says he's "very encouraged" by what he's heard since his exploratory committee was launched two weeks ago. 

O'Leary's advisers are said to realize he trails other candidates in terms of organization, but they believe his superior name recognition will make up for that.

Asked Monday about his ability to mount a ground game, O'Leary pointed to his reach on social media.

"It's a whole new ball game," he said. "I talk directly to Canadians every day."

If he wishes to enter the race, O'Leary must declare his candidacy by Feb. 24. The results of the leadership vote will be announced May 27.

About the Author

Aaron Wherry

Parliament Hill Bureau

Aaron Wherry has covered Parliament Hill since 2007 and has written for Maclean's, the National Post and the Globe and Mail.

With files from Hannah Thibedeau


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