One thing Donald Trump loves to say is that he knows how to make a deal. Even for our allies, sometimes the “art of the deal” can feel like a shakedown. And lately, Canada is the ally that’s been caught in Trump’s line of sight.
The president-elect has been trolling Prime Minister Justin Trudeau on social media, calling him the “governor” of America’s “51st State” — and threatening to impose a 25 percent tariff on Canadian imports if they don’t step up their game on border security. Adding to the drama this week, Canada’s government nearly imploded when Chrystia Freeland, Trudeau’s deputy prime minister and finance minister, resigned, citing Trump as a threat. In a scathing letter posted on X, Freeland said President-elect Donald Trump’s “aggressive economic nationalism” poses “a grave challenge.”
In an interview with the Playbook Deep Dive podcast, Kirsten Hillman, Canada’s ambassador to the U.S., downplayed any whiff of tensions between Canada and the U.S. “I think that the president-elect is having a bit of fun,” Hillman said. “Canada can take it. You know, we have a strong sense of who we are and we can dish it out.”
The U.S., she says, “is like family.”
And Hillman knows the president-elect well. During his last administration, she was instrumental in negotiating Canada’s side of the United States–Mexico-Canada agreement. And she flew down to Mar-a-Lago with Trudeau just a few weeks ago for that diplomatic dinner.
As close neighbors, the two countries have a lot of common interests, Hillman said, from border control to the fentanyl crisis to economic security. The president-elect’s mentions of tariffs, she says, “focused the mind” and helped Canada “make decisions faster than they were happening within our bureaucracy.”
Is that diplomatic double speak? Or is Trudeau’s government actually pleased to be riding shotgun with Trump along the northern border?
This conversation has been edited for length and clarity by Deep Dive producer Kara Tabor and senior producer Alex Keeney. You can listen to the full Playbook Deep Dive podcast interview here:
First and most important question. I heard you are a big fan of The Diplomat on Netflix. What tactics have you secretly stolen from Keri Russell’s character on the show?
Excellent question. So what I love about that show is that everything that happens in the show could happen and does happen, but often in a less glamorous way. Like I, for one, don’t have a private jet that jets me around. And I actually don’t have anyone to pack my suitcase for me. But OK, so one thing that I think is quite realistic is this show talks a lot about or you see a lot of information being shared, like important, secret intelligence. And that does happen. It doesn’t often happen when you’re wearing a ball gown and carrying a glass of champagne around an art gallery in Paris. It could, but more often, it happens in dark, secure boardrooms that have big metal doors and you’re wearing a black suit and a white blouse.
But in all seriousness, you guys have a lot going on in Canada and the possible next phase of the relationship between the United States and your country. For example, incoming President Trump posted on Truth Social on Nov. 25 about a 25 percent tariff on Canadian goods and services.
Four days later, you and Prime Minister Trudeau are in Mar-a-Lago meeting with folks and talking to him.
Let’s talk about this: How is your country preparing for the different types of relationships you’re going to have to have when Donald Trump takes office?
So first of all, that preparation has been ongoing for quite a long time. In advance of the election, we were involved in a very systematic effort to get out and reinforce relationships with Republicans and Democrats, traveling the country, making sure that we are making the connections that we need, talking to the people that are advising the Biden team and the Trump team — the Biden team was easier because they’re already in the White House and we know who they are — and then eventually, Vice President [Kamala] Harris’ team.
And building relationships, by the way, is not just like meeting people, and saying, “Hi, and I’m the ambassador. And here’s some things that are interesting to talk about.” It is very targeted towards understanding what their goals are: What are their policy priorities? What are they trying to get done if they’re elected? And in that conversation of understanding their goals and and gathering information, planting seeds with as many people as possible — here in D.C., and across the country — about what we can do together and how Canada can contribute to achieving the goals of the administration, [even if] we didn’t know who was going to win.
So now we are in the process of activating and working with those relationships, and hopefully nurturing the seeds that we’ve already planted. It is a Washington thing, but I’ve now met 42 governors. I spent a lot of time in places that are very reliant on Canada, either where they’re the best customer or we have massive investments, but they maybe don’t know it and they don’t think of us that often. So, you know, West Virginia, South Carolina, Texas and Arizona — I spent a lot of time in places that are nowhere near the border but have massive economic, security, military or whatever relationship with Canada. And we’re now using a lot of that information as we go forward.
One of the things that we as reporters realized when covering the first Trump administration and his campaigns is that his policy priorities can sometimes shift. His goals can seem unclear at times. So when you were having those conversations with leaders around the United States, what was the clarity that you actually got?
It’s interesting that you say that because I don’t think the policy priorities of the Trump administration are unclear at all. I think he’s doing exactly what he said he was going to do while he was campaigning. His priorities are the border and migration. Individuals, but also drugs — fentanyl — which Canada’s very, very eager to be working with the Americans on. We have a huge fentanyl crisis in Canada as well. Energy dominance. He’s sort of moved from energy security to talking about energy dominance, which is something more muscular, stronger than just energy security. Tariffs and economic tools that matter to him. So the things that he has been talking about that relate to us, that will matter for us in our relationship with the United States, I think have been pretty clear all along.
I think what people react to is the manner of communication — we’re just back to a very direct style of communication, a very sort of clear focus on his priorities and a style that’s a bit irreverent and a bit [like] it’s meant to kind of unsettle. But nobody should be surprised by this. I don’t think that the priorities are different. And I don’t think his manner of communicating with Americans and with the rest of us — I think it’s what we’ve seen before. So I feel like Canada’s not particularly on the back foot on this, we’re seeing what I think we thought would start to play out.
Deputy Prime Minister Chrystia Freeland left Trudeau’s government citing disagreements over how the prime minister dealt with the tariff threat from Trump. Some people thought that this was going to be the end of Trudeau. He seems to still be in office.
But right after Freeland left, we started hearing about your government’s new plan to spend, I think it was an extra $1.3 billion in border security; we started hearing about this joint strike force on the border between the U.S. and Canada — things that are clearly getting at what President-elect Trump was saying in his messages.
What I’ve heard from some American leaders is that this is what folks mean when they say that Trump is dominant on the world stage. He makes people do things.
Is that something that you guys are feeling? Like you are forced to deal with these issues now, because Trump was so clear about what would happen if you didn’t?
Obviously, a threat of a 25 percent tariff on a half-trillion dollars worth of trade a year, which is what Canada exports — we have an almost trillion dollar trading relationship, that’s about a $2.5 billion a day in trade — and so having a 25 percent tariff on that is what gets everybody’s attention.
So, to your first point: Absolutely. It got everyone’s attention. On the border though, I have to say that having the border as the issue that the president-elect wanted to work on with us right off the bat is a welcome development. And people may not perceive it that way.
Welcome because you guys wanted to work on it and the Biden folks didn’t want to?
No, because we were working on it already in Canada. Canada has, as I said, a massive fentanyl crisis. Sometimes we have more Canadians dying per capita per day than you do in the United States. And I don’t know if that’s necessarily well understood. The fentanyl precursors that we get largely come from China. But we are eager to work with the U.S. in a stronger way to try and figure this out. There is zero trafficking of fentanyl from Canada to the United States; it does not happen. There is illegal migration that happens between our two countries. I don’t want to suggest otherwise in both directions, but it pales in comparison, obviously, to what you guys experience at the southern border. Like, a bad weekend at the southern border represents the entire year of illegal migration between the United States.
So, one, the border is working well and we feel that it is well managed, but we were already quite eager to do more because we feel that the threats of, in particular, drug trafficking are not going to diminish. And so, when the prime minister and I and others went to Mar-a-Lago to discuss these issues, we were eager to say, “OK, what more can we do?”
And [after] the announcement that was made this week, we went back to Canada, we looked at the things that we were planning to do, and we accelerated. I mean, to be fair to the president, I think that he certainly gave everybody the focus of mind to accelerate and make decisions faster than they were happening within our bureaucracy. But it wasn’t like anything that was announced wasn’t well within Canada’s domestic interests anyway, that we wouldn’t have wanted to do anyway. And we are very happy and eager to cooperate more with your police services, your intelligence services.
So all of that is very good. So very happy to have had that conversation, and [give] credit where credit’s due.
Clearly, migration and some of these things are issues that are top of mind for Donald Trump and always have been. President Biden and his administration have been criticized — even from people in their own party — that it hasn’t been that same level of importance for them. Does it feel like a simple push from Joe Biden or Antony Blinken or whoever from the Biden administration could have fixed some of these things earlier on? Were they not interested in fixing some of these problems?
No. To the contrary. When President Biden came to Canada a couple of years ago, we amended this treaty that we have between our two countries that allows us to send illegal migrants back to each other’s country if they come across the border. … So this had an incredibly positive effect on disincentivizing illegal migration between our two countries. And [Biden] did that and it made a very big difference.
We also managed the border during the Covid crisis, which was complicated and I think very effective. But sadly, the criminality out there is not diminishing. And so we need to be constantly upping our game. But we’re also very pleased to be able to have maybe deeper partnerships in the law enforcement space with the incoming administration, which I think is a priority for them. So we’re happy to do that. So it’s not to say that it’s better. It’s just evolving with the times.
You talked about Donald Trump’s irreverent style of communication. After Trudeau’s meeting with him at Mar-a-Lago, he put on Truth Social that, “No one can answer why we subsidize Canada to the tune of over $100,000,000 a year? Makes no sense! Many Canadians want Canada to become the 51st State. They would save massively on taxes and military protection. I think it is a great idea. 51st State!!!”
Then, he called Prime Minister Trudeau the “Governor” of the “the Great State of Canada.”
How do you read those things? Does it feel like he’s minimizing you guys as a country?
I think that the president-elect is having a bit of fun. He started a joke during that dinner. And just to put it into context, this was really large. It was over Thanksgiving weekend. There was a lot of socializing. There was a lot of joking back and forth and that joke got picked up. And I think he’s enjoying continuing to run with it because it’s getting attention.
You don’t find it disrespectful?
No, it’s not. I mean, look, Canada can take it. We have a strong sense of who we are. We can dish it out. We can take it. And at some level, I actually have to say, we often think of Canada and the United States as being like family, like cousins or siblings.
And it feels a bit like sibling ribbing, which always comes with a bit of a tinge of pointedness, but ultimately is an expression of comfort in the relationship. So I don’t find it insulting.
What it sounds like to me is that during the first Trump administration, his tweets often came off as cause for alarm. But now you’re just used to it, because, like you said, it’s just ribbing. So what you and other leaders seem to want to do this time around is dig underneath the message and dig underneath the joke and find out what Trump is actually trying to get at.
Yeah. And as I say, he’s a leader who has very distinct goals and very clear priorities. And I’ve been here in D.C. for seven years. I’ve been leading the embassy here for five. And we’ve learned a lot about who he is. So we understand [his political and policy convictions] much better. We also understand him as a person.
People might find this surprising, but Prime Minister Trudeau and President Trump have a level of congeniality between them that maybe isn’t obvious to outsiders. But they enjoy talking about politics; they enjoy talking about their families; they enjoy talking about sort of the world stage and what’s going on there. They’re two G7 world leaders, right? There’s a lot they can talk about. And they’ve known each other a long time. And I think that is a big advantage to both our countries.
You’ve spoken about your seven years in Washington and the 42 governors you’ve met, but there is a new challenge with this new administration, which is that a lot of power seems to exist outside the normal channels. For example, Elon Musk seems to have the president’s ear. He had a big role in tanking this week’s continuing resolution. So I’m curious, how do you deal with that?
That’s a terrific question. And. It just goes to show the dynamism of diplomacy.
As we were preparing for the incoming administration, we did look to some of the people that we knew were close to President-elect Trump. And some of those are in his orbit, but some we didn’t predict. So as I said earlier, we kind of mined the relationships that we’d already created. But when there are new ones, we talk to Canadians. There are millions of Canadians in business, in academia and across our country that interact with Americans every day. So what I do is I reach out across our community, maybe our sub-federal leaders or our business leaders or some of our innovators, some of our scientists — it depends on the person — but you just try and understand where Canada might have a connection with some of these people. We are a smaller country. We are 43 million people. And so you can mobilize a lot of our country to make those connections where it may be harder for some of us who just have never crossed paths with them before.
You’ve dealt with different types of presidencies and different types of administrations — changes from Obama, to Trump, to Biden, to Trump again, to whatever comes next. What is the throughline that you find when dealing with our country? What is the thing that no matter what person is in charge of the country, is the same thing about America?
That’s a great question. Americans are proud. Energetic. Ambitious. Vocal. They are deeply proud to be Americans, even when they’re irritated with one thing or another. And I admire that greatly. I admire American ambition greatly. My youngest son spent his last two years of high school here, his junior and senior year, and I think it was incredible for him to do that because he was in an American school and he really got to see these traits of the American people that are at the core of the leadership that you play in the world. And I mean that very sincerely.
This is a country of fiercely intelligent, engaged, proud, dynamic and ambitious people. The American dream is a real thing. And people who are new to the country have it. But people who have been here for a long time have it, too. And I admire it greatly. That is the throughline.
And I think, from the perspective of Canada-U.S. relations, the throughline is that we are both countries greatly blessed to have each other as neighbors because there are a lot of countries around this world whose neighbors wish them ill, or do them ill. And we have a 5,000 mile border that anchors the most prosperous economic region in the world, probably the most secure region in the world and our relationship is only getting deeper.
Something that’s been interesting over the last few weeks is seeing Canadian leaders on American cable news talking about foreign policy. For example, Doug Ford, Ontario’s premier, threatening to switch off power for Americans; and Danielle Smith, Alberta’s premier, playing good cop and announcing this new border security program.
What’s it like having local officials publicly offering foreign policy advice about the relationship that you’ve helped to manage?
One of the big differences I find in Washington between myself and almost all of my ambassador colleagues is the way in which I deal with the American government, which is, more often than not, on domestic policy, not international policy. We have 18 agencies located here at the embassy, and the vast majority of them deal with domestic policy. I work with [Alejandro] Mayorkas and [the Department of Homeland Security] more than with the State Department, hands down. Of course we talk about international affairs, but it is a very domestically-focused partnership.
So those premiers who are talking about things that fall not exclusively, but partly in their areas of jurisdiction, are to be expected. And I think that they feel that they have important voices to bring to the American people, and I support that, I really do, because — I think it was Condoleezza Rice who coined the phrase that Canada-U.S. relations are more about “condo issues” than anything else, because we have this common territory, and so we have to work out our condo issues.
I think that the border, our electricity grid and our electricity relationship — those are both condo issues. They obviously have a bearing on our international relations. But it is different than my colleagues from Europe or Asia — it’s just different.
To put a finer point on it, it feels like they’re freelancing, right? Is that helpful as you’re trying to continue to build this strong relationship? It feels unhelpful.
Well …
I know I’m pushing the limits of our diplomatic language.
There’s no doubt in my mind that every sub-federal leader in Canada is trying to be helpful and is eager to make it clear that we are, at the same time, a very close partner who will do what we can to make sure that we are the best partner that we can be. But at the same time, we do expect in return that good partnership coming back our way. I think that’s the best way to say it.
Canada will absolutely lean in to the success of the incoming administration in every way that we can, and it is in our national interest to do so and we want to do so. There’s no country in the world that wants a strong America more than Canada, right? So we’re here for that.
But at the same time, we also have an expectation that a strong Canada is good for the United States.
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