To hear Donald Trump tell it, Canada is a suave international swindler, repeatedly conning American leaders and waltzing away with his country's money.

The U.S.'s neighbour to the north is "very smooth," has "outsmarted our politicians for many years," and has been "very rough" as it has "taken advantage" of the hapless superpower.

For months, the U.S. President has painted this portrait of Canada as Machiavellian manipulator in his public comments. Earlier this week, he took it to a new level.

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During a meeting with state governors to discuss school safety, Mr. Trump went on a lengthy digression about trade policy, rounding on his country's partners in the North American free-trade agreement, which is being renegotiated this week in Mexico City. Mr. Trump accused the slick Canadians of trying to trick him into believing the deal is working well.

"We cannot continue to lose that kind of money with one country. We lose a lot with Canada. People don't know it," he said. "Canada's very smooth: They have you believe that it's wonderful, and it is – wonderful for them. Not wonderful for us."

U.S. President Donald Trump said trade deals are stacked against the United States saying that he can't continue to let other countries "rob us blind." Trump singled out China, Japan South Korea and NAFTA members Canada and Mexico. The Associated Press

This doesn't exactly jibe with the Great White North's usual image – the guileless neighbourhood nice guy, maybe a little quietly insecure next to his hyper-confident next-door neighbour.

"'Canada is very smooth.' – Donald Trump," tweeted CNN pundit Chris Cillizza. "No one has ever said this about Canada before. Not ever. Never."

In the Reputation Institute's 2017 list of the best-regarded countries, an annual survey of 39,000 people in the world's 55 largest economies, Canada scored high on perceptions of public safety, ethics, effective government and favourable business climate. The country topped the list, just ahead of Switzerland and Sweden. (The U.S. was 38th, between Mexico and Venezuela.)

"It's both an unusual and exaggerated take," Stephen Hahn-Griffiths, Reputation Institute's executive partner and chief research officer, said of Mr. Trump's apparent image of Canada. "Outside of, maybe, some stand-up comics, there's no one with any substance who would characterize Canada in such a disparaging light."

Christopher Sands, director of the Center for Canadian Studies at Johns Hopkins University, said Mr. Trump's comments serve a political purpose: The Trudeau government has been lobbying free-trade-friendly governors and members of Congress, and encouraging them to pressure the White House to drop its protectionist demands in NAFTA talks. What Mr. Trump is trying to do, Mr. Sands argued, is drive a wedge between those American politicians and their new Canadian best friends.

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"When Trump says Canada is 'smooth' what he is doing is sending the message that what Canadian officials say sounds good superficially, but is not honest, and serves Canada but at the U.S.'s expense," Mr. Sands wrote in an email. "In a way, this is a compliment: it reflects the fact that Canada has made progress convincing US congressional and state leaders that Canada is right and Trump is wrong. But it also is bad news: it means that Trump is going to contest the Canadian spin on NAFTA and trade and is prepared to do so by challenging the stereotype of the honest Canadian Boy Scout."

In some ways, Mr. Trump's image of Canada is not all that different from his image of most countries. He won the election in part by arguing that the U.S. was repeatedly getting cheated, taking aim in turn at China, Iran and Mexico, among others.

In the last week alone, for instance, Mr. Trump described China as "killing us, absolutely killing the United States on trade."

The difference, of course, is that China is a nuclear-armed dictatorship of 1.4 billion people with ambitions of replacing the U.S. as the world's pre-eminent superpower. Canada is a close U.S. ally of 35 million with virtually zero chance of ever becoming a superpower, let alone the pre-eminent one.

Matthew Rooney, a former high-ranking American diplomat who ran the State Department's desks for Canada and Mexico, said Ottawa enjoyed broad respect within the U.S. government for its staunch commitment to NATO and NORAD, and for its role in the Afghanistan War.

Still, he said, Mr. Trump is correct in one sense: Canadians are shrewd negotiators. In bilateral talks on a range of issues over his time in government – from civil aviation to water rights – Mr. Rooney said Canada held its own at the bargaining table. The country was also known to lobby members of Congress, the White House and U.S. industry to put internal pressure on U.S. negotiators to modify their positions – much as it is doing now on NAFTA.

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"The Canadians were nice and approachable, but in a formal setting their negotiators were tough as hell," recalled Mr. Rooney, now director of economic growth at the George W. Bush Institute in Dallas. "There was a sense that the Canadians were very deft at playing a political card at the same time as they were playing a diplomatic card."

That said, Mr. Trump's view of Canada goes well beyond some grudging admiration for its negotiating skills.

"Canada does not treat us right in terms of the farming and the crossing the borders," he said earlier this month, without explaining what he was referring to. "We cannot continue to be taken advantage of by other countries."

And during a particularly rough patch in bilateral relations last April – during disputes over milk pricing and softwood lumber – he warned people not to be fooled by his neighbour's friendly demeanour.

"Canada's been very rough on the United States. Everyone thinks of Canada as being wonderful, and so do I, I love Canada," he said. "But they've outsmarted our politicians for many years."

Despite Mr. Trump's apparent fear of getting hosed by a country with one-tenth the economy of the country he leads, Mr. Hahn-Griffiths says that, by his data, the U.S. is still quite self-confident. But maybe Mr. Trump is on to something.

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"Maybe there's a growing doubt that the United States is the leading country in the world," he said. "I think some Americans would find it less easy to emphatically say 'yes' on that."