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There is the theory that President Trump is still bitter about his Canadian hotel ventures that went bust.

Some, on social media, have speculated that a 2019 photograph in which Justin Trudeau appeared poised to kiss Melania Trump, the first lady, at a Group of 7 gathering in France, left Mr. Trump with a grudge against the dashing Canadian prime minister.

And then there is the transactional view, that Mr. Trump sees the acquisition of Canada as the 51st state as the ultimate real estate deal that would seal his presidential legacy.

As Mr. Trump prepares to push ahead with a new round of tariffs on the United States’ neighbors to the north and south, he has expressed a special brand of loathing for Canada. The bullying of a country whose most prominent stereotype is that its people are “nice” has led to political upheaval in Canada and created both consternation and speculation about why Mr. Trump wants to engage in a trade war with America’s biggest trading partners. There is “no love lost” between the president and Mr. Trudeau, “With Trump, politics is personal.”

Mr. Trump has threatened to hit Mexico and Canada with 25 percent tariffs on all imports on Tuesday unless the countries do more to prevent migrants and drugs from flowing into the United States.

Intrigue abounds in Canada about why Mr. Trump has repeatedly belittled a neighbor and threatened to destabilize its economy with tariffs, a process that has brought relations between the two countries to a low point out.

As a businessman, Mr. Trump had two dealings with Canada that, while relatively limited, were both very public failures. The Toronto hotel and condominium project went into receivership in 2016. The following year, a hotel bearing the Trump name, again under license and with a similar management contract, opened in Vancouver, British Columbia. (Promotional material exaggerated the building’s height.) It failed, as well.