Freeland on Trudeau, Trump, and the Art of Leaving

There is a particular kind of candor that becomes possible only after the door has closed—when the meetings are over, the resignation letter has been sent, and the person who once sat at the cabinet table is free to describe what she saw there. Chrystia Freeland, Canada's former deputy prime minister and finance minister, has written that book. It is called Unreliable Boyfriend, and it is, depending on which chapter you read, a memoir, a policy manifesto, and a quiet settling of scores.

The title comes from a quip Freeland made in February on Real Time with Bill Maher, describing the United States under Donald Trump as not "a very reliable boyfriend" to Canada . The metaphor stuck. The book, subtitled An Insider's View of Dealing with a Chaotic Superpower, Plutocrats, and Other Complicated People, uses that relationship as its central frame .

Freeland's argument is that the United States has always been an "Uncle Sam"—a figure who "wants to be loved—and feared" . But under Trump, that uncle has become something worse than unreliable. He is, Freeland suggests, a bad partner: demanding adoration and capitulation, while offering little in return. Her prescription is what she calls "friendshoring"—a strategy of building closer trade and security ties with like-minded democracies to reduce dependence on both the United States and authoritarian regimes like China and Russia .

But the part of the book that has drawn the most attention is not the policy. It is the portrait of Justin Trudeau. Freeland served in his cabinet for nearly a decade, and she writes that "history will be kind to Justin Trudeau"—crediting him with the Canada Child Benefit, steering the country through COVID, and refusing to cave to Trump during the USMCA negotiations . Yet she also describes a leader who was "at his best with strangers" but profoundly aloof from his own ministers. She says she can count on one hand the number of times she met with Trudeau one-on-one .

She describes "crying was routine at cabinet meetings," with tissues kept on hand and hugs offered by the prime minister. She recalls a colleague being publicly scolded for using the word "crazy," with ministers instructed to say "bananas" instead . She says she stayed a year, maybe two, longer than she should have, and that Jean Chrétien encouraged her to weigh her loyalty to Trudeau against her responsibility to the party and the country .

Freeland resigned in December 2024, hours before she was to present the fall economic statement—a decision that helped precipitate Trudeau's own resignation weeks later . The book is being read, inevitably, through the lens of that rupture. But its author insists the unreliable boyfriend is not Trudeau. It is the country next door.

AI Image Disclaimer: All images in this article are AI-generated and serve illustrative purposes only, not as documentary records of the individuals or events described.

Sources: Toronto Star, The Globe and Mail, Western Standard, Traders Union, The Walrus