Donald Trump, as of late, has not been Canada’s loudest cheerleader.

A few weeks ago, the US president called Canada “the worst country in the entire world” during an informal press briefing in the White House during which he was asked about trade. Days later, he added that Canadian leaders were being “very bad” and needed to be “taught a little lesson.”

The feeling, it seems, is mutual. In July, an online Angus Reid survey of over 2,000 Canadians showed 79% had a negative view of Trump, with 69% of respondents reporting having a “very unfavourable” opinion of the US president.

So, with Trump’s return to office marking a rise in tensions in US–Canada relations, one might wonder: How do you deal with an administration that is simply not that into you?

That’s the question former deputy prime minister and former NAFTA negotiator Chrystia Freeland tries to answer in her new political memoir, Unreliable Boyfriend: An Insider’s View of Dealing with a Chaotic Superpower, Plutocrats, and Other Complicated People.

The Walrus spoke with her ahead of the release of her book. In conversation with Toronto-based journalist Wendy Kaur, Freeland explains what she calls the “doughnut strategy”: if the administration in the White House represents an obstacle, you go around it and find support elsewhere.

“We simply cannot capitulate to President Trump. With some people, maybe you make a compromise, and that’s how you get the relationship off to a good start. That is not Trump. He doesn’t read capitulation as a generous gesture in the service of relationship building. He reads it as capitulation and submission, and he pushes even further.”

— Chrystia Freeland, former deputy prime minister of Canada

Freeland’s approach to dealing with this “unreliable boyfriend” stands in contrast with how Jeremy Appel describes Alberta premier Danielle Smith’s.

In his book, Dark Phoenix: The Rise, Fall, and Re-emergence of Danielle Smith, which is excerpted in The Walrus, Appel describes her stance toward Trump as “obsequious” and “ingratiating.” He cites Smith’s “friendly” meeting with the president in his Mar-a-Lago residence in January 2025 and her refusal to sign a joint statement with the other premiers promising retaliatory tariffs against the US that same month.

Her attitude, he writes, has caught the attention of MAGA figures who have been pushing for Canada—or, in some cases, for Alberta— to become the US’s 51st state.

If you’re curious to learn more about what this all means for the upcoming October 19 referendum in Alberta, check out Jeremy Appel’s story here—and make sure you’re keeping up with The Walrus’s coverage of Alberta by reading our latest stories here.