Trump Threatens CEOs as Tactic Against Allies, Ex-Finance Minister Says

(Bloomberg) -- US President Donald Trump's administration privately pressures foreign CEOs and business leaders to bring their governments into line with the White House's demands, Canada's former deputy prime minister says in a new memoir.

"The Trump team is swaggeringly, rudely aggressive, even behind closed doors," writes Chrystia Freeland, who also served as finance minister, foreign minister and trade minister during Justin Trudeau's nine years in power. "Trump's cabinet secretaries miss no opportunity to warn foreign CEOs of the dire consequences if their leaders don't fall in line."

The book is titled Unreliable Boyfriend: An Insider's View of Dealing with a Chaotic Superpower, Plutocrats, and Other Complicated People. It combines behind-the-scenes accounts of her dealings with Trump and other US officials with a retelling of her dramatic split from Trudeau in December 2024.

The book's central argument is that America's allies have too often rewarded Trump's bullying with concessions that fail to produce results. Freeland makes it clear she was frustrated with people who complained privately but capitulated to Trump publicly — and warns that China is gaining greater power as a result of US policies.

"Too often today, America's allies perform the Trump-era equivalent of woke virtue signaling — too many of us talk tough about the United States, but carry a small stick. Too much is at stake for that sort of quisling behavior," Freeland writes.

She praises Prime Minister Mark Carney, her longtime friend, in whose cabinet she served for several months before her exit from politics. But she criticizes the government's decision in June 2025 to drop a digital services tax that would have affected US tech firms, only for Trump to hike tariffs on Canadian goods weeks later anyway.

While the most visible fight between the US and its allies is over tariffs, "the more consequential battle may be over Washington's insistence that Big Tech be allowed to operate freely around the world without being meaningfully taxed or policed," she writes.

The administration brings its demands directly to foreign business leaders. After Carney's famous "middle powers" speech at the World Economic Forum in Davos in January, Treasury Secretary Scott Bessent hosted a dinner with business executives. One guest at that event later delivered a stark message to Freeland, according to her.