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The words had scarcely been published on Tuesday evening when Canada's chattering classes lit up Twitter with titters.

That Justin Trudeau's Liberals had spent much of their time since last November making nice with the Trump administration was well documented. But the Prime Minister making showy public appearances with Ivanka Trump or his chief of staff becoming telephone buddies with Jared Kushner was one thing.

Now, The New Yorker was reporting a blooming bromance between Mr. Trudeau's principal secretary, Gerald Butts, and Steve Bannon, Mr. Trump's chief strategist, who is considered a driving force behind the U.S. President's flirtations with white nationalists. Not just that, but Mr. Bannon – currently on the outs with more mainstream White House staff, which was the main subject of the article – had come to see Mr. Butts as "a sort of left-wing version of himself."

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That Mr. Butts and Mr. Bannon get on well was not entirely a revelation, since it had been mentioned in Canadian media. And the magazine seemed confused about the details, getting wrong the particulars of a Canadian tax hike on the rich that Mr. Butts supposedly encouraged Mr. Bannon to push.

Yet however fuzzy the details, the timing of this account was fitting. It dropped literally on the eve of talks to renegotiate the North American free-trade agreement, an effort that might mercifully end the bizarre cross-border courtship. Rarely is a government embarrassed by having done something too well. But that is how ours could reasonably have felt as the New Yorker story landed, mere hours after one of the darkest moments of Mr. Trump's presidency, when he publicly drew equivalencies between neo-Nazis and people protesting against them.

After Mr. Trump's election victory last year, it was hard to imagine how some of his officials and Mr. Trudeau's could even be in the same room together. Presumably, they would see each other as conspiracy-minded demagogues on one side, Obama-worshipping elitists on the other.

For the Liberals, it might have scored short-term political points at home to position Mr. Trudeau as part of Mr. Trump's opposition. It also could have been disastrous economically, and in the long run, politically, to antagonize a president who wanted to overhaul Canada's biggest trade partnership. So the Liberals told anyone who would listen, and themselves, they would make the relationship work.

It was evident how difficult they expected that to be. A cabinet shuffle promoted Chrystia Freeland, the minister seen as most capable of navigating Trumpland; other ministers and officials went to Washington; provincial governments and opposition politicians and past prime ministers reached out to anyone south of the border who could influence the administration. Canada-U.S. relations became a focal point the likes of which Ottawa had rarely seen before.

But as they prepared for the NAFTA negotiations, there were at least two things the Liberals might not have fully anticipated.

One was the amount of nose-holding that cozying up to Mr. Trump would require. Like many others, they seemed to convince themselves before his inauguration that the presidency would normalize him. Instead, they find themselves stepping carefully while other foreign governments criticize the President, now accused of equivocating on white supremacy.

The other was how desperate for friends Mr. Trump's top advisers would be. Increasingly isolated, and at war with one another, they are eager for allies where they can find them. So as Mr. Kushner is said to frequently turn to Ms. Telford, Mr. Bannon is apparently enthusing to journalists about his new pal Mr. Butts.

Possibly, such relationships – and those with more conventional officials – could be useful beyond continental relations. Some foreign policy experts have suggested Ottawa could step up a role it has intermittently played in the past by serving as a sort of translator between Washington and other countries. At times of potential global conflict, that could be a huge service.

But the NAFTA negotiations have not started a moment too soon. The courtship that preceded them was going to yield diminishing returns, if it had not already – and not just because it would keep getting harder for the Liberals to look at themselves in the mirror.

It becomes harder every day to be seen as friends of this administration without some guilt by association, harder to be true to Canada's values as Mr. Trudeau's government sees them and potentially harder to pursue any international goals beyond preserving cross-border status quo.

Interviewed for a recent Globe and Mail profile, Ms. Freeland insisted words matter in wielding global influence. She was referring to speeches defending open borders, minority rights or feminism. But at a certain point, words that carefully avoid offending Mr. Trump might not count for much – and praise from one of his most toxic advisers could be downright unhelpful.

The foreign affairs minister says Canada is looking to include chapters on gender and Indigenous peoples in the new North American free-trade agreement. Chrystia Freeland says a gender chapter was part of a trade deal with Chile.

The Canadian Press