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Canada's ambassador to the U.S., David MacNaughton, in Toronto. Mr. MacNaughton says with time, Trump will recognize how important America’s relationship with Canada is, but only if Canada makes an effort to show him.

Melissa Renwick/The Globe and Mail

It is surely not what David MacNaughton bargained for when he was appointed last winter to his dream job.

An insider's insider who since the 1970s has spent his career moving deftly between political backrooms and corporate boardrooms, Justin Trudeau's erstwhile campaign official seemed a perfect choice to navigate Washington as Canada's ambassador to the United States.

But that was the Washington of Barack Obama and Hillary Clinton, maybe Jeb Bush or Marco Rubio. Donald Trump's Washington stands to be a very different place – one in which a pragmatic lifelong Liberal could feel much less at home, his sensibilities offended on a daily basis.

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Read more: What does the Trump era mean for Canadians? A survival guide

Analysis: Trudeau and Trump a study in contrasts

Read more: With Trump's tax plan, Ottawa must act to prevent economic exodus: David Dodge

And yet, here we are, chatting over breakfast at the King Edward Hotel – one of his favourite haunts in his hometown of Toronto, where he's back for a long weekend – and Mr. MacNaughton is doing a passable job of sounding as though he not only has come to terms with Mr. Trump's looming presidency, but actually welcomes the opportunities it presents.

"He's going to have problems all over the world," Mr. MacNaughton says of a president-elect by many accounts already overwhelmed by the scale of a job he didn't really expect to win. "And this is a place he can actually have a friend, in the sense of Canada being such a friend of the United States. Whether on infrastructure, defence, security, even trade – if I were him, I'd be looking to us to show that he can actually get stuff done."

Mr. MacNaughton's frequent claim during our conversation that there are plenty of mutually beneficial interests for Mr. Trump and Mr. Trudeau to pursue, despite wildly divergent world views, may be the sort of spin a diplomat has to offer. But because he's delivering it not just to the Canadian public but to the Prime Minister's Office and cabinet, it's spin that puts him at the forefront of a debate about Canada's role in a free world with Donald Trump as its leader.

More so than many ambassadors, Mr. MacNaughton – a friend and mentor to both Katie Telford and Gerald Butts, Mr. Trudeau's chief-of-staff and principal secretary, respectively – has the ear of the Prime Minister he serves. And he seems likely to use that voice to counter calls to put distance between this country and an incoming U.S. administration strongly disliked by a vast majority of Canadians.

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Even before Mr. Trump's shocking victory, there were calls for Mr. Trudeau to speak out against his demagogic and, in some cases, overtly racist messages. Should Mr. Trump make good on his more offensive campaign promises, such as targeting Muslims with restrictive immigration policies and ramped-up surveillance or deporting millions of Mexicans, those calls – from media, opposition politicians, fellow Liberals – will ramp up. And so, too, will expectations from abroad that, in the face of a nationalist push toward closed borders not just in the U.S. but much of Europe, Mr. Trudeau capitalize on his global profile to champion liberal internationalism.

Mr. MacNaughton isn't asking Mr. Trudeau or anyone else to bite their tongues altogether. "My advice to everyone – this goes not just to cabinet, but to caucus and my kids – is that it's important that we articulate our values, the values of Canadians, in terms of generosity and inclusiveness and tolerance," he says when asked about his message when he spoke at a recent federal cabinet meeting. But he suggests that should be more in the sense of "reasserting as Canadians our values as they apply to each other," not doing it in a pointed "we are and they're not" way.

"We shouldn't shy away, either individually or collectively, from the values that we espouse as a nation," he says about the balance between building a relationship with Mr. Trump and presenting a face to the rest of the world. "I think Canadians expect us to show those values and articulate those values in anything we do on a multilateral basis. Having said that, it is really important also that when you're playing on the world stage, the essential element of that is, is this in Canada's interest to be doing that?"

On specific policy discussions, Mr. MacNaughton argues for choosing battles carefully – avoiding getting bogged down in irreconcilable differences, even if about matters of high priority to Mr. Trudeau, such as a continental effort to fight climate change.

"Well … it'd be a bit of a task," he says wryly when asked whether there's any hope of convincing Mr. Trump – who has expressed skepticism about whether climate change is real, at one point claiming it's a Chinese hoax – to take the issue seriously. "Look, there are some areas, this being one, where there's a clear division of opinion. My own view is whether it be personal or governmental relationships, you're better to focus on the things you agree about and not the things you don't."

Trade policy, he insists, could prove one of the areas of consensus. Yes, Mr. Trump is set to deep-six the nascent Trans-Pacific Partnership, to which Canada was a signatory, and has threatened to tear up the North American free-trade agreement. But once the president-elect wraps his head around the "depth and breadth" of trade and investment across his country's northern border – responsible for nine million U.S. jobs, Mr. MacNaughton likes to point out – he will presumably see the need to "work together rather than being at cross-purposes."

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Mr. MacNaughton's implication is that mutually beneficial tweaks to NAFTA (not a full "renegotiation," a word he says he hasn't used despite headlines shortly after Mr. Trump's victory suggesting he did) could allow both sides to declare victory and move on. While others speculate about what those changes could involve – perhaps easier cross-border mobility for certain professions, or resolutions to long-standing disputes over specific industries, such as softwood lumber – he declines to start negotiating in public.

Besides, having likely given little thought to the intricacies of Canada-U.S. trade, Mr. Trump and members of his administration will need to be brought up to speed before diving deep into discussions.

On shared infrastructure investments (perhaps to speed cross-border traffic), on continental energy strategies (including not just the possible revival of the Keystone pipeline project, but also such things as transmission of Canadian-generated power south of the border), on defence (the frequent joint missions and daily intelligence-sharing that often flies under the radar), Mr. MacNaughton tells a similar story. The relationship runs so deep already that Mr. Trump should with time recognize opportunities to continue building it to mutual advantage, but only if Canada mounts an unreserved effort to make him recognize them.

"They just haven't thought about it," he says of the incoming administration's grasp of the economic relationship in particular. "It's just like, 'Oh yeah, I like the Canadians, they're nice people,' but I don't think they really understand the degree to which their prosperity and ours are linked." So it falls not just to the federal government but "the provincial governments, the business community, labour, others" to educate.

That also means, for Mr. MacNaughton, insulating Canada from volatility in the White House by forging ties at other levels of government. "This is not a system like ours where because the person ends up as prime minister with a majority government, they can do everything," he says, highlighting that he's spent much of his first year on the job travelling the U.S. meeting with state governors and other regional leaders.

And in the meanwhile, he's going out of his way to convince people back home not to panic in the face of Americans' stunning election decision and, at least insofar as how Mr. Trump's rise affects Canada's interests, to keep an open mind.

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Whether that will remain possible or desirable if Mr. Trump lives up to worst fears by targeting minority populations, indulging authoritarian impulses or picking fights globally is anyone's guess. And even now, the Prime Minister served by Mr. MacNaughton will be taking considerable domestic political risk if he is seen to be sidling up to Mr. Trump.

The ambassador begs off a question about such risk, saying that sort of politics is no longer his purview. Trying to explain his own optimism, though, he harks back to his political staffing days, when he served as principal secretary (alongside Mr. Butts as policy director) in the early days of Dalton McGuinty's Ontario premiership.

"For the first two weeks the briefings were coming in and everything was a problem," he recalls. "I remember Gerald and I sitting around saying, 'Oh my God, not another …' and I remember saying: 'You know, what we should do is every time one of these things comes in, just say what an opportunity.' Because then you think of things in a different context.

"So the way I look at it right now," Mr. MacNaughton says of working with Donald Trump's America, "is we've got lots of opportunities."

MacNaughton's musings

On what he told cabinet before the U.S. election

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"When I made the presentation at the cabinet retreat in August, I was obviously asked what I thought was going to happen. I said that all the smart people in Washington said that Hillary was going to win and Democrats were going to win the Senate and Republicans would hold the House, and the only thing everybody should understand was that all the smart people in Washington had been wrong every single time during the last year."

On Trump not necessarily representing a huge change from Canada's perspective

"What I did before the election [with Canadian politicians] was to try to highlight the areas where there were differences between the Obama administration and Clinton and Trump, but also the areas where there actually wasn't much difference. There may be differences in rhetoric. But the Democrats have been worse – what I'd call worse – on trade than the Republicans, in terms of the Congress. Hillary Clinton, Barack Obama and Donald Trump in their own ways have described burden sharing, in other words other countries stepping up to the plate on defence. Everyone's had an emphasis on security. And Bernie Sanders, Hillary Clinton, Donald Trump have all talked about improving the lives of the middle class."

On members of the Trump administration he's gotten to know already

"I've met [chief of staff Reince] Priebus before, he was at the embassy, I chatted with him a couple of times. I've had a couple of conversations with Senator Jeff Sessions [Mr. Trump's choice for Attorney-General], mostly about college football, but we talked about the Canada-U.S. relationship and the depth of it and everything else. Particularly with people like him who are from Alabama, who don't come from Great Lakes states or border states, they have a fond view towards Canada but it's not a terribly in-depth one."

On the ongoing debate about whether most Trump supporters were motivated by racism or by economic anxiety

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"When you find people talking about the good old days, or expressing attitudes about others, it's usually as a result of economic insecurity. The United States is a country like ours that was built by immigration and openness and generosity. And the only time that is challenged is when people are having economic insecurity. I attribute most of it to economic insecurity."

On lessons for Canadian politicians from Americans' rebuke to their political establishment

"I think the most important thing you learn from it is don't spend all your time talking. Make sure you listen, and I mean really listen, to what people are saying. Because that's the only time you're really going to be able to talk to them in terms that indicate that you understand what they're feeling.… You get into that bubble, and with all of the pressures in government, it's like drinking out of a fire hose. You actually need to spend more time listening to what people have to say because that's where you're going to get a sense of what their priorities are. Particularly these days.… If people think you think you're too important to talk to them, and you only want to talk to important people, you've got a problem."

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