Mark Wiseman, seen here in this November, 2017, photo, has a career in business and an Ivy League education – the sorts of things that tend to impress U.S. President Donald Trump.Mike Segar/Reuters
When Mark Wiseman arrived as Canada’s ambassador to the U.S. on Sunday, he walked straight into a diplomatic crucible.
U.S. President Donald Trump has pushed bilateral relations to their lowest point since the War of 1812 with punishing tariffs, threats to tear up the deal that governs continental trade and demands that Canada be annexed as the “51st state.” More than three months ago, he abruptly broke off talks to end the trade war.
Mr. Wiseman, a 56-year-old veteran of Bay Street, Wall Street and three major public pension funds, is Ottawa’s first envoy to Washington not to come from a political or diplomatic background.
He does, however, have extensive international experience landing complicated deals. He succeeds Kirsten Hillman, a career civil servant and trade negotiator who served as ambassador for more than six years.
With more than $1.2-trillion in annual trade and countless jobs on the line, the new ambassador will face the ultimate test of his negotiating prowess.
“We’re throwing a guy into a lion’s den,” said Jim Leech, the former chief executive of the Ontario Teachers’ Pension Plan, where Mr. Wiseman worked in the 2000s. “He is as prepared as anybody could be to deal with this uncertain future and very difficult counterparty.”
Here are four challenges Mr. Wiseman faces.
Tariffs and the USMCAOpen this photo in gallery:
The tight integration between the Canadian and U.S. economies has meant that Canada has been disproportionately hammered by Mr. Trump’s global trade war – particularly his tariffs on steel, aluminum and autos.
Prime Minister Mark Carney, Ms. Hillman and Intergovernmental Affairs Minister Dominic LeBlanc tried for months last year to negotiate a way out with Mr. Trump and U.S. Commerce Secretary Howard Lutnick. Despite concessions by Ottawa, including rolling back retaliatory tariffs and cancelling a planned digital services tax on large technology companies, a deal remained elusive.
Then, the President took umbrage with an anti-tariff ad run by the government of Ontario this past October and abruptly ended talks with a Truth Social post.
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The Prime Minister has said he now expects attempts to get the tariffs lifted will be rolled into the review of the United States-Mexico-Canada Agreement, or USMCA, scheduled for this year. Other friction points in those negotiations will be Canada’s Online Streaming Act, which requires services such as Netflix and Spotify to fund and promote Canadian content, and the country’s protectionist supply-management system for dairy and eggs.
Mr. Trump has also said he may simply end the USMCA instead of revamping it. His Trade Representative, Jamieson Greer, has indicated that he intends to negotiate with Canada and Mexico separately, a divide-and-conquer strategy.
One thing that shouldn’t be a problem for Mr. Wiseman, according to those who know him, is wrapping his head around the complexities of an economic relationship that spans innumerable sectors governed by hyperspecific trade rules.
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Michel Leduc, chief public affairs officer at the Canada Pension Plan Investment Board, where Mr. Wiseman worked for 11 years, including as CEO between 2012 and 2016, said his former boss had to stay on top of business opportunities, economic conditions and political context to oversee investments in dozens of countries.
“Running a massive global portfolio across every conceivable economic sector demands the business acumen of many multiple chief executives combined,” he said.
Defence and drugsOpen this photo in gallery:
Anna Moneymaker/Getty Images
It’s not just a trade negotiation.
Mr. Trump has also raised a laundry list of grievances, demands and potential opportunities with Ottawa since returning to power. He has accused Canada of not doing enough to crack down on fentanyl coming into the U.S. He has pressed Canada to jack up its defence spending. And he has raised the possibility of Canada joining his planned Golden Dome missile defence system.
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Mr. Carney has responded with tougher border measures, a pledge to spend 2 per cent of GDP on defence this year and a willingness to join the Golden Dome. One of Mr. Wiseman’s tasks will be to figure out what more, if anything, Canada can do on these files that would help close a trade deal.
Diminished returns on the outside gameOpen this photo in gallery:
Andrew Harnik/The Associated Press
During Mr. Trump’s first term, then-prime minister Justin Trudeau executed a Team Canada strategy, in which federal ministers, provincial premiers and business leaders fanned out across the U.S. to build relationships with their American counterparts.
The goal was to reinforce at the local level how many U.S. jobs were dependent on trade with Canada – and to get members of Congress, state-level politicians and U.S. companies to put pressure on the White House to preserve free trade. The approach was particularly effective because most of Mr. Trump’s own Republican Party disagreed with his protectionism.
This strategy appears to have been significantly less effective during Mr. Trump’s second term. In part, this is because Mr. Trump’s near-total control over the GOP has meant the party has been much more united behind his agenda than it was eight years ago. It may also be a facet of Mr. Trump’s own resolve: He has been willing to go much further on tariffs this time around.
U.S. House votes to end some of Trump’s tariffs on Canada in rare rebuke by Republicans
Still, there are some indications that this may change. Six House Republicans broke with their caucus last week by voting to end some of Mr. Trump’s tariffs on Canada. The move was mostly symbolic, as Mr. Trump is expected to veto the bill if it passes the Senate, but it could be a sign that he will come under increased pressure to dial back the levies. Democrats, meanwhile, might take control of Congress in midterm elections this fall. And polls show voters are frustrated with Mr. Trump’s handling of the economy.
Christopher Sands, director of the Center for Canadian Studies at Johns Hopkins University, said that Mr. Wiseman may play an information-gathering role for Mr. Carney. The ambassador could, for instance, try to quietly suss out what the White House would be willing to agree to or who in Congress might be helpful for Canada.
“Wiseman could come in and be the person to say, ‘Well, what is Trump’s real bottom line, and how is he thinking to deal with Congress after the midterms,’” Prof. Sands said. “Somebody who can talk to a lot of people discreetly and gather a better picture of what’s going on in the U.S. could be valuable.”
The mercurial PresidentOpen this photo in gallery:
One theoretical advantage of Mr. Wiseman’s background: His career in business and Ivy League education – he went to law school at Yale – are the sorts of things that tend to impress Mr. Trump. They may also help him build relationships with Mr. Lutnick and Treasury Secretary Scott Bessent, both career financiers.
Still, it’s a perilous path. Mr. Trump has made clear that he calls all the shots. And, unlike during his first administration, no one around him seems to seriously challenge his ideas.
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And as Mr. Carney has discovered, it’s not easy to maintain a relationship with someone as erratic as Mr. Trump. After repeatedly lauding the Prime Minister for months, Mr. Trump soured on Mr. Carney after the latter’s defiant speech to the World Economic Forum and efforts to boost trade with China. A steady stream of Truth Social threats followed, including one rambling post that claimed a deal between Canada and China would somehow result in Beijing abolishing the Stanley Cup.
Mr. Leech said Mr. Wiseman will certainly seek to figure out how decisions are made in the White House, including to what extent Mr. Lutnick and Mr. Bessent can influence Mr. Trump. The biggest challenge, however, will be handling a President who frequently changes his mind.
“Practising keeping your cool is really important,” he said. “Sometimes when I read something that Mr. Trump has said, I want to throw the newspaper across the room. But Mark’s reaction is going to have to be ‘Okay, circumstances have changed, facts have changed. Let’s see how we deal with this.’”