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The President’s son-in-law has become Canada’s main man at the White House.Pablo Martinez Monsivais/The Associated Press

Given U.S. President Donald Trump’s affinity for golf, engaging in the game is advantageous for a diplomat. Canadian Ambassador David MacNaughton, an avid player, has golfed with some prominent lawmakers. But has he ever strolled the fairways, he was asked, with the big cheese himself, the cantankerous leader of the free world?

“I was supposed to play with him,” he responded.

How’s that?

One day last year his friend the Australian ambassador, a guy called Joe Hockey, excitedly told Mr. MacNaughton he had a big game lined up for them at the Trump course across the river in Virginia. “Be there at 12:45 p.m. tomorrow.” The Canadian envoy begged off. Other commitments, he told him. Joe Hockey pressed him further but the response was still negative.

“Okay. Your loss.”

Next day at 12:45 p.m., Mr. MacNaughton got a text message from his Aussie friend. He was on the first tee with Mick Mulvaney, the then-budget director, and also with Mr. Trump. Too bad you couldn’t make it!

Mr. MacNaughton, as could be imagined, felt the blood draining from his arteries. He was mad as hell that he hadn’t been told the game would be with the President.

For shank diplomacy, it ranked high on the charts. It’s a good thing, at least, that Mr. MacNaughton has other Trump family contacts, one being his son-in-law Jared Kushner. Not just any son-in-law, the tall, lean 38 year old, dismissed initially as being in over his head, an example of nepotism run amok, has ascended the White House pecking order to the point where he’s now regarded as the second most powerful figure in there.

Mr. MacNaughton got to know him during NAFTA renegotiations. Not only did Mr. Kushner take part, he was pivotal. He brought clout to the table. He was more flexible than other American negotiators. And most important, everyone knew to whom he was reporting at day’s end.

Looking back on the negotiations, Mr. MacNaughton paid him quite the compliment. "Without Jared Kushner,” he said over dinner this week, “we would not have had a trade deal.”

The President’s son-in-law has become Canada’s main man at the White House, our key contact and best hope for getting a rocky bilateral relationship back on track. Last week, Mr. MacNaughton, who has dined at the Kushner residence, called him to say he had a host of issues to discuss. He was ushered in for a lengthy session during which one big topic was Arctic sovereignty. The Russians are mobilizing, beefing up their presence, he told Mr. Kushner. Sovereignty with U.S. help has to be reasserted.

Normally that would be an issue for the State Department. But Secretary of State Mike Pompeo has shown little interest in Canada. Too much else on his plate.

Help from Mr. Kushner, however, has only gone so far. Where is he on major issues such as Mr. Trump’s steel and aluminum tariffs, which have yet to be lifted despite Ottawa’s repeated pleas? They currently stand in the way of ratification of the USMCA trade deal.

U.S. trade negotiator Robert Lighthizer’s temper boiled over recently when news reports appeared citing Mr. MacNaughton saying that “more out of sadness than anger” Ottawa might have to impose more retaliatory tariffs.

Mr. Lighthizer subsequently confronted the ambassador saying he’d better realize that “more out of anger than sadness,” he would hit back real hard at Canada if that happened. A commonly used expletive frequently made its way into the discussions.

Another pressing issue is China, which is currently detaining Canadian citizens. This is very likely a result of Washington’s request that Canadian authorities arrest a Huawei Technologies executive. The U.S. is close to terms on a trade deal with Beijing. If that happens without resolution of the detainees issue, Mr. MacNaughton has warned Mr. Kushner and others that it will be a travesty.

Prime Minister Justin Trudeau hasn’t spoken with Mr. Trump for a few weeks but there is no bad blood, the ambassador says. During the SNC-Lavalin controversy, he noted, the President displayed some friendship toward the Prime Minister, calling him to offer words of encouragement.

The coming weeks are critical to relations. Mr. Trump wants the trade deal ratified. With an election looming, Mr. Trudeau needs it even more. He needs the tariffs removed, he wants the China tensions settled. It means his ambassador better be knocking on Jared Kushner’s door. Many times.