Former Canadian Deputy Prime Minister Chrystia Freeland is publishing a book titled "Unreliable Boyfriend: An Insider's View of Dealing with a Chaotic Superpower, Plutocrats, and Other Complicated People" in October 2026. the title stems from a quip she made on Bill Maher's show in February 2025, calling the United States "not a very reliable boyfriend right now ." According to The Canadian Press, the book is part political memoir, part international analysis about the evolving role of the United States, drawing on Freeland's journalism career and her decade in Canadian cabinet from 2015 to 2025.

The February 2025 Maher comment that launched a book deal

Freeland's offhand remark on "Real Time With Bill Maher" became the hook for her upcoming memoir. the phrase "unreliable boyfriend" captured a sentiment widely held among Canadian politicians and trade partners during Donald Trump's presidency. as the source reports, publisher Simon & Schuster Canada says the book will offer readers an up-close view of power, edited by Jonathan Karp. The October 2026 release date places the book just after the upcoming CUSMA review, adding potential political weight.

Trump's 2018 jab: 'We don't like their representative very much'

Freeland was a central figure in negotiating the Canada-United States-Mexico Agreement (CUSMA), which is up for review next month. her relationship with Trump was notably contentious; in 2018, days before the deal was signed, Trump said: "We don't like their representative very much." The book is expected to provide an insider account of those tense negotiations. According to the report, Trump's dismissal of Freeland personally underscores the high-stakes diplomacy she navigated while serving as minister of international trade, foreign affairs, finance, and internal trade over a decade.

From Trudeau's cabinet to Zelenskyy's adviser and Rhodes Trust CEO

Freeland's political trajectory took dramatic turns: she resigned from Justin Trudeau's cabinet in December 2024 just hours before delivering the fall economic statement, then rejoined under Mark Carney, only to leave politics entirely in early 2026. the Canadian Press notes she then became an economic development adviser to Ukrainian President Volodymyr Zelenskyy and accepted the role of CEO of the Rhodes Trust. These post-politics roles give her unique vantage points on both global security and elite institutions—likely material for the book's analysis of "plutocrats."

What's still unknown: Trump's reaction and CUSMA review timing

The book arrives as CUSMA faces a mandated review next month, raising questions about whether Freeland's insider account could influence perceptions of the agreement. key open questions include: How will Trump or his allies respond to the book's portrayal of his administration? Does Freeland's role as a senior adviser to Zelenskyy shape her view of US reliability as a security partner? The source provides only Freeland's perspective; there is no comment from US officials or from Trump himself. Readers will have to weigh the memoir's candor against the inevitable bias of a key participant.