MARCH 20, 2025
As President Donald Trump argued in recent weeks — for the first time, the third time, the 10th time — to eliminate Canadian sovereignty and convert the country into America’s 51st state, messages started arriving in attorney Mitchell Wine’s inbox.
“A couple friends wrote me and said, ‘It’s all your fault,’” Wine recalled with a chuckle.
Wine does not, in fact, believe it’s all his fault. Back in 2016, he represented a group of investors who sued Trump, the Trump Organization and others, alleging they received false information while purchasing condominiums at the Trump International Hotel and Tower in Toronto. Possibly because of Trump’s controversial brand, the hotel’s business struggled. The investors lost money. The building went into receivership, Wine’s clients settled, and Trump’s name was ultimately removed from the building.
The terms of the settlement were confidential, and Trump never admitted wrongdoing.
Now, years later, people in Toronto are looking at the failed real estate venture and wondering: Is that why Trump is so obsessed with Canada?
“I have no idea,” Wine said.
A White House official, speaking on the condition of anonymity to detail the president’s thinking, insisted that the 51st-state concept sprung unbidden into Trump’s mind, that it’s a serious proposal, and that it’s motivated by his belief that annexation would benefit Americans and Canadians alike.
“As President Trump has said, Canadians would benefit from lower taxes and secure borders as residents of America’s cherished 51st state,” White House spokeswoman Anna Kelly said.
Canadians say Trump’s vision for Canada as an American accession is insulting, infuriating and — increasingly — a serious threat to their national security. A U.S. invasion may not be imminent, they acknowledge, but they believe that Trump’s insistence on tariffs against Canadian imports is a real effort to weaken the country’s economy to a point that annexation might be a more serious consideration.
“It’s one thing to say it before you’re sworn in. It’s another thing to say it from behind the seal of the United States on the podium,” said David McLaughlin, a Canadian policy expert who was chief of staff to Canadian Prime Minister Brian Mulroney. “We’re asking ourselves: Why does he keep saying that? It must be because he wants it to happen.”
The theories on exactly what — or who — prompted Trump’s brainstorm range from grand to granular.
The Canadians who’ve emailed Wine have suggested that the failure of Trump hotels in Toronto and Vancouver left Trump with the desire for revenge on Canada. (A White House official, speaking on the condition of anonymity to detail the administration’s thinking, called this suggestion “absurd” and said the real estate ventures have “absolutely nothing to do with it.”) Others, including Matthew Holmes, executive vice president and chief of public policy at the Canadian Chamber of Commerce, have argued that Trump’s annexation talk is a reflection of his antagonistic relationship with former Canadian prime minister Justin Trudeau, whom he has previously called “very dishonest and weak.”
Ontario Premier Doug Ford speaks about the new tariffs the United States has placed on Canada during a news conference on March 4 in Toronto. (Nathan Denette/The Canadian Press/AP)
In interviews, current and former Trump allies, politically connected Canadians and foreign-policy experts suggested other theories, including that right-wing influencers, Trump’s policy advisers or even a chance encounter at Mar-a-Lago earlier this year could have influenced Trump to begin his 51st-state crusade.
But many Canadians are simply confused.
“Your guess is as good as mine,” Doug Ford, the premier of Ontario, said when asked about the genesis of Trump’s aspiration to admit Canada to the Union. “We’re dumbfounded as to why he’s doing this.”
Former Trump administration officials don’t recall the “51st state” coming up during Trump’s first term. Former commerce secretary Wilbur Ross and former national security adviser John Bolton told The Washington Post they’d never heard Trump raise the issue before.
But Gerald Butts, who was a principal secretary to Trudeau, said in a recent social media post that the idea came up “a lot” during the president’s previous interactions with Trudeau.
Trump began publicly referring to Canada as the “51st state” before his second inauguration, and he has consistently escalated his rhetoric in the first two months of his presidency.
He has argued that incorporating Canada into the United States would reduce Canadians’ taxes, enhance border security and improve Canadian military defenses.
“To be honest with you, Canada only works as a state. … It would be one of the great states anyway — this would be the most incredible country,” Trump said in the Oval Office on March 13. “Visually, if you look at a map, they drew an artificial line right through it, between Canada and the U.S., just a straight artificial line. Somebody did it a long time ago, many, many decades ago, and it makes no sense,” Trump continued, apparently referring to a 1908 treaty that settled the boundary between the U.S. and Canada. “It’s so perfect as a great and cherished state.”
Many Canadians say they no longer view Trump’s statements as a joke or bombastic negotiating tactic in the tariff war.
“The ironic thing is, I’ve sat down with endless Republicans,” said Ford, who last week moved to briefly impose a surcharge on electricity imports to the U.S. before reversing that decision. “Not one Republican agrees with him. Behind closed doors, they tell me they have no idea why he’s doing it.”
Pete Hoekstra, Trump’s nominee to be the next ambassador to Canada, seemed similarly unsure of what to make of his boss’s comments. During his Senate confirmation hearing last week, Hoekstra was asked whether he agreed that Canada is a sovereign nation and should not even jokingly be referred to as the 51st state.
“Canada is a sovereign state, yes,” Hoekstra said. “How the president and the relationship between the former prime minister and Canada — the characteristics and nature of that relationship, uh, I don’t know, okay?”
Memes and jokes about a potential Canadian annexation circulated in right-wing circles online in the year leading up to the 2024 election. Former Fox News host Tucker Carlson and political commentator Tim Pool both mused about the potential for an invasion of Canada — or, in Carlson’s words, “liberating the great nation of Canada from itself.”
Trump also posed the possibility of Canadian annexation over dinner with Trudeau in late November, according to reports from the time — though a Canadian minister who was present for the meeting insisted shortly after that the then-president-elect was only joking.
President Donald Trump and Canadian Prime Minister Justin Trudeau in 2019 arrive for a meeting with other NATO leaders at a hotel in Watford, England. – Evan Vucci/AP
Since then, Trump’s interest in annexing Canada has become more emphatic.
The British newspaper the Telegraph has suggested one potential source: Peter Navarro, Trump’s adviser on trade, who has been promoting the president’s tough terms on tariffs against Canada. (When asked about whether Navarro has pushed the idea of annexation, a White House official said, speaking on the condition of anonymity to detail the president’s thinking, said, “The president came up with the idea himself.”)
Another possible influence: Kevin O’Leary, a.k.a. “Mr. Wonderful,” a.k.a. one of the investor stars of the “Shark Tank” reality TV show.
O’Leary, who is Canadian, has been making the case in recent months for a formal economic alliance between the U.S. and Canada, similar to the European Union. He envisions a combined immigration system, mutual citizenship and a shared currency.
“China is the problem right now, and it’s going to remain so as it tries to become the world’s largest economy,” O’Leary said last week. “If somehow we combine the economies of Canada and the United States — game over. It’s over. Nobody could touch us.”
O’Leary was one of many people in Trump’s orbit who flew to Mar-a-Lago in early January to mingle with Trump before the inauguration. During that time, O’Leary recalls, he had a conversation with Trump about Canada, his family’s dual connections to Canada and the United States, and his affinity for both countries.
“I don’t know if it was something I said that got him thinking about that,” O’Leary said last week. “And that was the beginning of something. But I can’t claim that I gave him the idea. Who knows? I have no idea.”
On Jan. 6, Trump posted on Truth Social: “Many people in Canada LOVE being the 51st State. … If Canada merged with the U.S., there would be no Tariffs, taxes would go way down, and they would be TOTALLY SECURE from the threat of the Russian and Chinese Ships that are constantly surrounding them. Together, what a great Nation it would be!!!”
Trump’s allies say it’s all tough talk meant to enhance his negotiating position in the U.S.-Canada trade war.
“I don’t think it’s real for a lot of reasons,” former House speaker Newt Gingrich said. “The Senate would be somewhere between Democrat and socialist for the rest of history. I would not take it as a serious project.”
Canadian observers say their outrage at Trump’s attacks have fueled unprecedented levels of unity and collective defiance.
“I can’t understate how much this is visceral in Canada,” said Holmes, the Canadian Chamber of Commerce official. “People are feeling a true sense of betrayal. It’s personal.”
The attacks from Trump seem to have buoyed Canada’s Liberal Party, which had been primed for an electoral wipeout.
Ordinary Canadians, meanwhile, have begun committing conspicuous acts of patriotism. Shoppers at grocery stores are reading the labels of items on the shelves to make sure they’re avoiding U.S.-made products. Canadians say they have never in their lives seen so many maple leaf flags flying. The mayor of Mississauga announced Saturday that, “at the request of many,” the city has started to remove all American flags from sports arenas and locations along Lake Ontario.
“We’re not the most unified country in the world,” said Wine, the lawyer who was asked if his clients’ case had fueled Trump’s anti-Canada sentiment. “But these days, we are. These days, we love Canada even more because we are so offended by the president’s behavior.”
Courtesy/Source: Washington Post
