As the public feud between Donald Trump and Canadian Prime Minister Mark Carney heats up, investor and television personality Kevin O’Leary has dropped what he calls the decisive “hook” in the standoff—one insight that reframes the entire confrontation as less of a crisis and more of a high-stakes negotiation neither side can afford to lose.

The tension centers on Trump’s sudden threat to impose 100% tariffs on Canadian goods, a sharp reversal from his own comments just 10 days earlier.

On January 16, Trump openly praised Canada’s engagement with China, telling reporters it was “a good thing” and that Canada “should do that.” Now, he’s furious—warning of severe trade punishment.

So which Trump is real?

According to O’Leary, both are—and that’s the point.

“To understand this moment, you have to go back about 12 months,” O’Leary said, tracing the roots of the dispute to the final days of Justin Trudeau’s government. Trump, he noted bluntly, despised the previous leadership team in Ottawa and made no secret of it.

When Carney took office and quickly removed Chrystia Freeland, it sent what O’Leary described as a “very strong and very positive signal” to Washington.

That reset laid the groundwork for what followed. And then came the numbers.

Since Carney entered office, Canada’s stock market has surged 34% in just 11 months, snapping what O’Leary called a “decade-long economic coma.” Over the same period, the Canadian dollar climbed another 5.4%. By contrast, the S&P 500 is up roughly 14%.

“You’ve made close to 40% going long Canada,” O’Leary said. “Why? Because the world believes this is a giant negotiation.”

Markets, he argued, understand Trump’s style. He is transactional, personal, and pressure-driven. Tariff threats aren’t necessarily endpoints—they’re leverage. And Carney, O’Leary insists, knows that.

But then came the tell.

In the past 48 hours, Trump announced plans involving Greenland and missile defense systems—a move O’Leary believes exposed Washington’s real strategic priority. With missile coverage planned from Alaska in the west and Greenland in the east, Canada sits squarely in the middle.

“That hole in the middle?” O’Leary said. “That’s Canada. And you don’t build that defense dome without a deal with Canada.”

Suddenly, the power dynamic looks very different.

While 70% of Canadian exports flow to the U.S., Canada is the top export destination for 36 U.S. states, and the largest trading partner for 26 of them. This is not a one-way dependency. It’s mutual—and deeply embedded.

That’s why O’Leary believes the tariff threats are unlikely to last.

On the China question, O’Leary was unsparing. He warned that China has “screwed every business partner it’s ever had” since entering the WTO and called it the economic, military, and AI adversary of both Canada and the U.S. In his view, Canada’s limited sectoral arrangements with China—covering areas like canola exports and capped EV access—do not change the strategic reality.

The endgame, O’Leary predicts, isn’t tariffs or trade wars. It’s convergence.

“No tariffs between these two countries,” he said. “Some kind of EU-style relationship. No loss of sovereignty—but full economic alignment.”

Why? Because only a combined North American economic bloc, spending heavily on technology, deterrence, and enforcement, can effectively counter China’s scale and ambition.

And that’s why markets remain calm—even optimistic—as Trump and Carney trade sharp words.

“They’re squawking now,” O’Leary said. “But they’re kissing cousins soon.”

In other words, the noise isn’t the story. The leverage is.

Trump may be escalating rhetorically. Carney may be projecting restraint. But underneath the theatrics lies a reality neither side can ignore: Canada and the United States are too strategically intertwined to break apart.

The fight looks explosive.
The data says otherwise.