Two Drinks with. . . the Woman Who Handled a Trade War Against Trump

By The Free Press | Created at 2026-10-16 23:36:30 | Updated at 2026-10-17 00:03:12 30 minutes ago

Unlike most of us, Chrystia Freeland saw Donald Trump coming from about 450 miles away, from her perch in Ottawa as a top government minister under former Canadian prime minister Justin Trudeau. Back in 2016, she told me when we met a few weeks ago, “we were sufficiently alive to the possibility that Trump would win that we actually had the Department of Trade produce a paper on what we should do if the United States were to threaten to withdraw from NAFTA.” They suspected Trump might tear up the North American Free Trade Agreement, which had knit their countries and Mexico together for more than two decades.

That, of course, is exactly what happened—the first shot in a stochastic trade war that has escalated since then, and is still roiling politics in both countries. Trump came into office with the view that Canada, rather than being America’s closest ally, was actually “ripping us off.” Freeland would spend the better part of seven years in the middle of that fight as her country’s lead negotiator, helping strike a replacement deal in 2018 before things collapsed again in Trump’s second term.

She recalled all of this to me at a fancy hotel in Manhattan, where we met for lunch. She was visiting the city to promote her new book—Unreliable Boyfriend: An Insider’s View of Dealing with a Chaotic Superpower, Plutocrats, and Other Complicated People. That provocative title refers to none other than Trump, whose years of broken promises and gaslighting rhetoric have left Canadians, who were long smitten with America, feeling totally jilted. “No one was allowed to go around saying mean things about him,” Freeland said of the Trudeau cabinet during Trump’s campaign and the early days of his first term. Even the smallest slight risked torching the two countries’ relationship.

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