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Why did Trump take another shot at Chrystia Freeland during the Oval Office meeting with Carney?

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One of the challenges Prime Minister Mark Carney faced in the Oval Office on Tuesday was stickhandling around President Donald Trump’s insults of other politicians, including Canada’s minister of transport and internal trade, Chrystia Freeland.

Despite Trump saying the Canada-U.S.-Mexico free trade agreement is still a good deal, Trump levelled an insult aimed at Freeland.

As Canada former federal minister of international trade, Freeland was Canada’s lead negotiator for the 2018 treaty. Without mentioning her by name, he called her a “terrible person” on Tuesday, a comment he made during the negotiations too.

There was no reaction from the Canadians, or other Americans, in the room.

“Trump seems to have an attitude that many of us have experienced when working with an abusive employer,” says University of Toronto political science professor, Ryan Hurl. “The boss expects his subordinates to take everything he says in stride, even the worst insults and provocations. if you respond to the provocations, the boss will not only be angry but insulted.”

Hurl assumes Trump found “Freeland’s lack of deference” unsettling, he said in an email to National Post.

Over time, Trump has repeatedly expressed negative opinions about Freeland. He has publicly called her “terrible,” a source of “ill will for Canada,” and “whack” — particularly criticizing her role in trade negotiations and her approach to Canada-U.S. relations.

During the CUSMA negotiations, he said, “We don’t like their representative very much,” referring to Freeland.

After Freeland resigned as Canada’s finance minister in late 2024, Trump posted that her “behavior was totally toxic, and not at all conducive to making deals which are good for the very unhappy citizens of Canada. She will not be missed !!!”

Jeni Armstrong, who teaches political communication at Carleton University, said she finds it curious that Trump would continue to harp on Freeland.

“I think a lot of Canadians — women in particular — are asking themselves that question,” she wrote in an email to National Post. “It’s pretty well documented that the president takes issue with strong and effective women who don’t share his political leanings (Hillary Clinton, Kamala Harris, Nancy Pelosi, Alexandria Ocasio Cortez … it’s a long list).”

Rob Danisch, professor of communications at the University of Waterloo, shares that view. In an email to National Post, Danisch says that Trump is “not really capable of viewing any woman as anything other than an object. Hence, Freeland is caught in this … rhetorical pattern.”

Trump was likely “looking to Carney, as another man, to confirm his view of women as objects.”

Freeland has responded with her own theory about Trump’s insults. In early 2025, she posted on X that the reason both Trump and Vladimir Putin have complained about her is: “I don’t back down – and Trump and Putin know it.”

Regarding Carney’s lack of reaction to Trump’s insult of Freeland on Tuesday, Armstrong says: “There was zero upside for Prime Minister Carney to engage on it, so I’m not surprised that he didn’t.”

“I’m struck by how needy he is for others’ complicity, says Rob Goodman, politics and public administration professor at Toronto Metropolitan University. “He’s aware that he’s breaking some sort of rule (otherwise he’d simply mention Freeland by name), and he wants everyone else in the room to get their hands dirty with him by acknowledging that they   do know who he is talking about,” he wrote in an email to National Post.

He thinks Carney “did a good job of not taking the bait. But I think we saw a glimpse of what makes Trump an effective demagogue — his instinct for inviting others to participate in his abuse.”

He also points to a worldview that he thinks is inherent in Trump’s comments as well as the direction of U.S. trade policy: “So while it is tempting to write off comments like these as the product of one man’s animosity or sexism, they matter because the American side in yesterday’s negotiation has fully bought into the worldview they represent. When Trump and the members of his administration talk about trade, they talk about “manly” manufacturing jobs, “weak” European beef, and spoiled girls who have too many dolls.”

Armstrong doesn’t think there is any implication in the Trump’s Freeland comments for the future trade negotiations.

“I don’t think we can or should make a connection between these specific comments about Freeland and the future of trade negotiations … We don’t know if she is going to have a meaningful role in whatever negotiations take place.” Carney seems to be taking a pragmatic approach to Trump and trade, Armstrong says, “so it’s possible that if she stays in cabinet, he may elect to assign her a role that’s not obviously related to the trade file.”

Danisch agrees: “I think given that Freeland is not likely to be a major part in future trade negotiations that this will not be relevant, or relevant to the extent that Trump will be more willing to work with a man because he sees men as having agency and being important decision-makers, a role a woman cannot have in his worldview.”

In noting the difference in Trump’s overall demeanour yesterday, Hurl points out that Freeland and Trudeau took Trump’s 51st state rhetoric seriously and literally, but says Carney was more strategic. “Carney has reacted in a way that Trump has more respect – ignore the jokes and simply get down to negotiation.”

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