Kirsten Hillman says leaving Trump's Washington now was 'the most responsible thing'

Her departure doesn’t take effect until sometime “early in the new year,” so for now she’s still going flat out.

Last spring, the prime minister “asked me if I would be willing to stay.” She was, to help the transition, “but I also said that I wasn’t interested in staying on for another term as ambassador.”

In an interview Wednesday with the Star, Hillman said she’ll help ease the entry of a new ambassador whom the prime minister said he will name “in the coming weeks.” Carney refused comment on reports that financier Mark Wiseman is in line for the job while former Quebec premier Jean Charest’s name is also in play.

The prime minister praised Hillman as an “exceptional public servant” who has “done a fantastic job for Canada” although Carney misstated her ambassadorial tenure as four years. In fact, Hillman’s time in Washington spanned eight tumultuous years, six as ambassador. 

A lawyer by training, career public servant, and an experienced trade negotiator, Hillman navigated Washington’s swampy diplomatic waters with aplomb, deepened ties with federal and state lawmakers, American CEOs, and mingled easily with Republican and Democratic decision-makers on political convention floors or inside the Oval Office.

She won plaudits across social media and in the House of Commons Wednesday for her skilled performance in the high octane posting. 

Former Canadian ambassador in Washington Frank McKenna said, “Ambassador Hillman’s going to go out with her head high, with a lot of respect from people on both sides of the border. She really had to perform heroically.”

Although Canada is “well-served” by its professional diplomatic corps and Hillman was very “savvy politically,” McKenna said the Washington diplomatic post is unique, and at this critical time requires someone with a “political pedigree,” who has the ear of the prime minister, who is “wired into the business world” on both sides of the border, who has trade expertise and is at ease communicating through media.

“This is a president and administration more likely to to get their policy from cable news than they are from briefing notes. And so you’ve got to be able to get there on Newsmax or CNN or Fox News and mix it up with the host and represent Canada and Canada’s perspective,” said McKenna.

Hillman said she realized over recent months that leaving now, ahead of the scheduled 2026 Canada-U.S.-Mexico Agreement (CUSMA) review, made sense, after intensive trade talks faltered this fall.

“It’s becoming clear that more and more our discussions with the United States are going to be coming under — or in the context of — the USMCA, the CUSMA discussions,” Hillman said Wednesday. “And those discussions are gonna take a while.

“So it just seems like the most responsible thing for me … is to not stay on until we’re many months into that and then depart, but actually depart at the beginning, assist with the transition so a new team is in place that sees it from start to finish.”

Carney said there is a “window” now for a new ambassador to get up to speed before the formal review gets underway in earnest, a signal he doesn’t expect any re-start anytime soon.

Hillman and her co-lead in those talks, Canada-U.S. Trade Minister Dominic LeBlanc, had been negotiating to adjust the punishing U.S. 50-per-cent sectoral tariffs on steel and aluminum, and 10-per-cent levies on energy. Other major sectors like autos, dairy, or digital services were expected to be tackled months later, in the broader review of the trilateral agreement.

U.S. President Donald Trump suspended sectoral talks in late October after he was rankled by an Ontario-led ad blitz that slammed the economic damage of tariffs, using a Republican hero of the president’s, quoting Ronald Reagan’s own words. Since then, the president has shown little interest in re-starting negotiations.

Hillman plans to retire from the public service and return to her Ottawa home. “I’m going to spend some time with my family and reflect on what comes next. I’m honestly not sure what that’s going to be. I’ve got a few ideas, but I’m going to think it through and take some time to decide.”

The Canadian team will miss her advice.

Hillman skillfully negotiated Canada’s entry into Asia’s free trade deal, the Comprehensive and Progressive Agreement for Trans-Pacific Partnership, and after joining the D.C. embassy in 2017, she helped stickhandle the NAFTA re-negotiation of Trump’s first presidential term and the first round of U.S. global tariffs on steel and aluminum. She was named ambassador by Justin Trudeau in 2020, and presented her credentials to Trump, before his Democratic rival Joe Biden took office. 

Though the Canada-U.S. dynamic is tense at the moment, Hillman says there is an evident personal connection between Carney and Trump.

“It’s clear that President Trump respects Prime Minister Carney. There is no question of that. And not only because of how he (the president) sort of interacts with him, but because he says it. He comments on the prime minister as a strong leader, as a smart leader, as a successful politician, a successful person. These are the kinds of terms that he uses when he’s talking with the prime minister and when he’s talking about the prime minister. 

“I don’t think it’s going to solve all of our problems and challenges, but it is certainly important that they have this strong relationship and line of communication.”

Reflecting on her work as a diplomat, Hillman said she “never felt” at a disadvantage being a non-politician dealing with political counterparts — cabinet-level officials and White House members.

“Yes, they’re politicians, but they’re also appointed to those jobs,” she said, unlike Canada’s cabinet members. “They come with backgrounds and expertise from different areas. And I have found that my unique expertise in Canada-U.S. relations in general, trade in particular, has opened doors for me.”

Hillman also never felt disadvantaged operating as a woman in a male-dominated Washington world. “I feel that I have been very effective and I have built all the relationships required to provide the best possible advice to Prime Minister Carney, Prime Minister Trudeau before him, Prime Minister Harper, before them when I did the TPP negotiations. And that was an Asian trade agreement where there were very, very few leading women at the table.”

Asked what Canada needs now in a Washington ambassador, Hillman doesn’t hesitate: someone skilled at building relationships and trust. 

“The most important thing that you can offer … is insight on the dynamics on the ground regarding those who are making the decisions for the president and his close advisers, in real time and with depth and sophistication. And in order to do that, you need to build relationships here in Washington and around the country with businesses, CEOs, with political leadership, and with this other layer of individuals who are influential in particular with President Trump.”

That elicits “additional information and insight that you can bring then to the prime minister and his team to help them make the most effective decisions,” she said, “because the (U.S.) decision making is being led by a certain group of people and it’s always evolving and so you really have to be nimble to have your finger on the pulse of how that’s going down.”

Hillman said it’s not clear whether her successor will wear the same two hats she had as chief negotiator in the trade talks and ambassador, and neither the PMO nor LeBlanc’s office could clarify.