WARMINGTON: Mr. Wonderful goes to Mar-a-Lago as speculation ramps up about PM’s future

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Published Jan 05, 2025 • Last updated 1 hour ago • 5 minute read

Kevin O’Leary speaks to the Empire Club of Canada at a luncheon in the Arcadian Court in downtown Toronto on Friday April 7, 2017 during the Conservative Party leadership race.

With speculation swirling that Prime Minister Justin Trudeau may be getting ready to take a walk in the snow at Rideau Hall, one of his biggest critics was taking a walk near the beach at the famous Florida residence of the incoming U.S. president.

While all eyes are on Prime Minister Justin Trudeau in Ottawa right now, one couldn’t miss Kevin O’Leary at Mar-a-Lago with the president-elect this weekend.

Just what were Donald Trump and O’Leary talking about?

“Just a couple of guys talking,” joked the Canadian investor and media personality.

So much to talk about.

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The Toronto Sun has confirmed O’Leary was not just at the Palm Beach “Winter White House” with the soon-to-be 47th president Saturday night, when Italian Prime Minister Giorgia Meloni was there, but was invited back Sunday.

“Going back again tonight,” the Shark Tank star told me.

This is just 15 days out from Trump’s inauguration for a second term on Jan. 20.

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Could the potential of Trudeau leaving office into his 10th year as PM have come up in the conversation? It’s certainly on the tip of many tongues in the political world as they wonder if the sun will finally set on Trudeau’s “sunny ways.”

Time will tell. If it’s happening, as many speculate, it was news to Trudeau’s own half-brother Kyle Kemper, who while a critic of his older sibling as prime minister cares about him as a family member since their mother is none other than Margaret Trudeau. He said he’s heard nothing internally about Trudeau resigning. But if it is the end for Trudeau, “I don’t think he’s stepping down on his own accord,” said Kemper.

While there are dozens in the Liberal caucus who are calling for him to leave, there is no official mechanism they can pull to make it happen. Meanwhile, as Trudeau clings to power, it seems there are efforts to rag the puck.

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Justin Trudeau beside Donald Trump at a dinner table.

Prime Minister Justin Trudeau, left, shared this image to social media a day after meeting with U.S. president-elect Donald Trump at his Mar-a-Lago residence in Palm Beach, Fla.

Whatever ends up going down, as the Toronto Sun‘s Brian Lilley reported, all members of the Prime Minister’s Office have been ordered to be in the building on Monday.

Perhaps that was on the agenda in the gab fest between O’Leary and Trump. But there are other potential topics on the agenda, too.

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O’Leary, a.k.a. “Mr. Wonderful,” had turned a lot of heads over Christmas when he floated the idea of going down to talk to Trump about the idea of negotiating a European Union-style economic partnership between Canada and the U.S. that sees no tariffs on trade, passports at the border and the Canadian dollar at par with the greenback.

He said he could be there within 48 hours.

Well, less than a week later, like Trudeau did in November, there was Mr. Wonderful at Mar-a-Lago — as seen in an X post talking with Trump and billionaire financier and philanthropist Bill Pulte. In addition to Trudeau, were they talking about Canada-U.S. relations or comparing Shark Tank ratings with The Apprentice?

“Yes to all of those questions,” teased O’Leary.

It clearly raises another question: Could O’Leary end up finding himself inside of Trump’s inner circle the way Elon Musk is? If he’s going back for a second visit, clearly the incoming president is comfortable with him being around there.

And the man who the polls say would win a massive majority to become Canada’s next prime minister, Pierre Poilievre, gets two thumbs up from O’Leary for his economic plans, which he believes will help make Canada competitive again.

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As for those criticizing O’Leary for making suggestions, while they are entitled to their opinion it must be said that the former Shark Tank star was always clear he was merely offering some ideas to unburden the red tape and woke rules to help both countries rise to become the world’s powerhouse in terms of energy and economics.

There’s nothing wrong with having that discussion. It should be had and O’Leary broaching it is a good thing for Canada. It’s certainly better than seeing a country sinking into the abyss and drowning with debt as the dollar and economy collapses.

When it comes to preventing the 25% tariffs that Trump has threatened on Canadian goods, it should be all hands on deck to work on a good working relationship. O’Leary is the perfect guy to start that conversation.

Meanwhile, the focus shifts to Ottawa where there is much speculation about Trudeau’s future as many suggest he could step down as prime minister as early as Monday or at Wednesday’s caucus meeting. He could also prorogue Parliament to give time for a leadership contest or even go the governor general to call an early election.

Can Justin Trudeau prorogue the House until April, May or June to have a long Liberal leadership race?
I’ve been looking into it and this is what I found out. pic.twitter.com/ZElaebYknP

— Brian Lilley (@brianlilley) January 5, 2025

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As of Sunday, the PMO was not responding to media requests. It’s anybody’s guess.

The country may find out Trudeau’s plans soon, but while he hasn’t done any media since Chrystia Freeland quit as finance minister, in any social media he has done Trudeau has made it clear 2025 is an election year and he plans on being the president of the G7 meeting set for Kananaskis, Alta., in July. Could he prorogue Parliament and stay on as PM until the Liberal government elects a new leader?

Even as he continues to face hecklers and dismal poll numbers, it would still seem surprising to see the PM throw in the towel from such pressure.

Even with political pundits saying his caucus is hellbent on pushing him out and that he just has to accept that the gig is up, count O’Leary among those who are skeptical about Trudeau resigning.

“No, he won’t do it,” declared O’Leary.

While O’Leary has encouraged Canadians to work to oust Trudeau, he doesn’t see the PM being the type to talk away.

This may come down to the voters. Who said Canadian politics is boring? Stay tuned. We may find out what comes next as early as Monday.