Trump Outmaneuvers Canada’s Prime Minister in Oval Office Showdown

This was “The Art of the Deal” unfolding in real time.

If you’ve read The Art of the Deal, none of this should come as a surprise.

Today’s meeting between President Trump and Canadian Prime Minister Mark Carney played out like a live-action masterclass in Trump’s dealmaking philosophy. From thinking big to pushing relentlessly, the meeting followed the exact playbook Trump laid out in his 1987 bestseller.

Think big.

Be relentless.

Maximize your leverage.

Get the word out.

And when someone treats you unfairly, fight back.

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Trump began the meeting by congratulating Carney on his election victory and offering warm praise that helped ease some of the tension in the room. It was classic Trump: build rapport first, then move the pieces.

But what happened next caught everyone off guard.

Carney, who had built his entire campaign around posturing against Trump, suddenly flipped the script.

“Thank you for your hospitality, and, and above all, for your for your leadership,” Carney said. “You're, you're a transformational president.”

He then echoed Trump’s policy priorities—focusing on the economy, the border, and the fight against fentanyl—and presented them as his own vision for Canada.

“I've been elected—to transform Canada, with a similar focus on the economy, securing our borders… much greater focus on defense and security, securing the Arctic and developing the Arctic.”

He also reiterated the potential for renewed cooperation between the two countries, saying:

“We’re stronger when we work together… I look forward to… finding those areas of mutual cooperation so we can go to work.”

Trump, clearly pleased, replied:

“That's great. Very nice. Thank you very much. Very nice statement.”

Then came the moment everyone had been waiting for: the 51st state pitch.

A reporter asked if Trump’s earlier comment about Canada joining the United States had been a joke.

“Well, I still believe that, but, you know, it takes two to tango, right?” Trump replied without hesitation.

What followed was pure “think big” Trump.

“I mean, I believe it would be a massive tax cut for the Canadian citizens. You get free military, you get tremendous medical care and other things. There would be a lot of advantages, but it would be a MASSIVE tax cut.”

He then brought the conversation back to his roots in real estate.

“When you get rid of that artificially drawn line—somebody drew that line many years ago with like a ruler—just a straight line right across the top of the country… I’m a very artistic person. But when I looked at that beauty, I said, that’s the way it was meant to be.”

Still, he made it clear that nothing would be forced.

“We’re not going to be discussing that unless somebody wants to discuss it… But I do feel it’s much better for Canada.”

Across from him, Carney shifted in his seat as Trump laid out his grandiose vision.

Trump belted out:

“It would really be a wonderful marriage, because it’s two places they get along very well. They like each other a lot.”

Cornered by the scale of Trump’s proposal, Carney felt compelled to respond.

“As you know from real estate, there are some places that are never for sale,” he said.

“Having met with the owners of Canada over the course of the campaign, last several months, it’s not for sale. Won’t be for sale, ever.”

But then came the real signal—and likely what Trump had been aiming for all along.

“But the opportunity is in the partnership, and what we can build together. And we have done that in the past.”

Carney then shifted to national security, pledging a “step change” in Canada’s defense posture and a stronger U.S.–Canada partnership.

He followed that up with a major announcement: Canada would now pay its fair share toward NATO.

“The president has revitalized international security, revitalized NATO, in us playing our full weight in NATO.”

Trump’s big vision was already producing results.

Moments after Carney declared that Canada was not for sale, Trump pushed again.

A reporter asked:

“Does this make the discussion a little more difficult to start on?”

Both men shook their heads.

“No, not at all,” Trump said.

Then came a vintage Trump moment—his relentless style to keep the deal alive on full display. And the media was eating it up.

His message was going to get out loud and clear.

“Time. Time will tell. It’s only time,” he said. And then, with a grin:

“But I say, never say never.”

“I’ve had many, many things that were not doable, and they ended up being doable—and only doable in a very friendly way.”

Carney sat quietly, visibly uncomfortable.

Trump wasn’t letting the idea die.

“But we’ll see. I mean, over time. We’ll see what happens.”

He wasn’t backing off the deal. He was simply letting it breathe.

As the meeting wrapped up, Trump made one final point—and reminded everyone who held the leverage.

A reporter asked: “Are you prepared to walk away from that pact?”

Trump replied: “From what pact?”

“USMCA,” the reporter clarified.

Trump responded calmly but clearly: “No. No, it’s fine. It’s there. It’s good. We use it for certain things,” he said, gesturing toward Carney. “The USMCA’s a good deal for everybody.”

Then he pivoted—and delivered a pointed message.

“I won’t say this about Mark, but I didn’t like his predecessor,” Trump said.

“I didn’t like a person that worked for him, she was terrible, actually. She was a terrible person. And she really hurt that deal very badly because she tried to take advantage of the deal and she didn’t get away with it.”

“You know who I’m talking about?”

“We had a bad relationship having to do with the fact that we disagreed with the way they viewed the deal, and we ended it… we ended that relationship pretty much.”

This was Trump living out another one of his core principles: fight back when treated unfairly—and don’t forget who tried to take advantage.

Then he gave Carney a final reminder:

“We do have a negotiation coming over the next year or so to adjust or terminate it.”

The message was unmistakable.

It wasn’t just a meeting. It was The Art of the Deal—live and in real time.

Massive thanks to Overton for racing against the clock with me to get this report out as fast as possible. You can dive deeper into his brilliant work by subscribing to his personal Substack page below.