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Washington State Park workers put up a new American flag in front of a Canadian flag atop the Peace Arch in Peace Arch Historical State Park, in Blaine, Wash., on Nov. 8, 2021.Elaine Thompson/The Associated Press

The Canadian government is making a full-court press to prepare for a potential second Donald Trump presidency, aiming to avoid a repeat of 2016 when his victory caught Prime Minister Justin Trudeau’s cabinet by surprise.

Much of the Team Canada push is public facing. Led by Ambassador Kirsten Hillman and Industry Minister François-Philippe Champagne, it has entailed cabinet ministers, provincial premiers and Canadian business leaders fanning out across the U.S. to build relationships with American counterparts.

Some of it is more discreet. Late last month, Ms. Hillman and Mr. Champagne played host to a meeting at a Washington restaurant with former Trump administration officials, said a source in the Canadian government with knowledge of the outreach. Two of the Prime Minister’s top advisers, meanwhile, worked the after-party circuit around the White House Correspondents’ Association dinner, another source said.

The Globe and Mail granted confidentiality to the two sources, both Canadian government officials, to learn details of private conversations.

The goal of Ottawa’s strategy is to pre-empt any policies that could damage Canada after November’s election by reinforcing to Americans how much their economy relies on its northern neighbour. The Republican Mr. Trump and Democratic President Joe Biden are neck-and-neck in the polls.

“Whether it’s a Republican or a Democratic administration, and regardless of the composition on Capitol Hill, there is a strong tendency towards protectionism,” Ms. Hillman said in an interview. “While those policies are designed to create or reshore or buttress American jobs, when you cut, break down Canada-U.S. supply chains, which are so deeply integrated, you have the opposite effect.”

The ambassador recounted one meeting with Elise Stefanik, the upstate New York congresswoman angling to become Mr. Trump’s vice-presidential running mate. The pair discussed cross-border investments in Ms. Stefanik’s district, a 45-minute drive from Montreal. At a sit-down with Ted Cruz, Ms. Hillman said, he was eager to talk about his Canadian roots – the Texas senator was born in Calgary – something he pointedly avoids doing with U.S. audiences.

The Trudeau government’s current push replicates its inside-outside game during the renegotiation of the North American free-trade agreement, rebranded the U.S.-Mexico-Canada Agreement or USMCA by Mr. Trump. At the time, the Prime Minister’s advisers cultivated back-channel relationships with White House insiders while also building a broader coalition of U.S. politicians and businesses to lobby the administration to drop its most protectionist demands.

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That effort, however, only began after the election, which the second Canadian official said Mr. Trudeau’s government had not expected Mr. Trump to win. This time around, the idea is to ramp up the outreach before the vote.

Daniel Ujczo, an Ohio trade lawyer who represents businesses on both sides of the border, pointed out that Mr. Trump’s campaign and allied think tanks are also working ahead. In an effort to avoid the disorganization that marked his first term, they are already drafting policy and vetting people for future White House jobs.

“The one consistent theme from the folks in a potential second Trump administration is that they’re prepared this time,” said Mr. Ujczo, who is also an honorary Canadian consul. He cited recent events in Detroit with Ms. Hillman and Trade Minister Mary Ng, and in Cleveland with Mr. Champagne as important for creating alliances in the U.S.’s trade-dependent industrial heartland.

Mr. Trump has promised a 10-per-cent tariff on all goods. He could also trigger a renegotiation of the USMCA in 2026, in which he might revive demands from last time, such as rewriting auto industry rules to force companies to move plants out of Canada and Mexico and into the U.S.

There has been friction between Canada and the Biden administration over Buy American procurement rules and disputed oil pipelines. But such disagreements have tended to be narrow, unlike Mr. Trump’s threats to end North American free trade.

The second Canadian official said the Trudeau government is trying to understand exactly how Mr. Trump would apply his agenda to Canada if he wins, as well as what a re-elected Mr. Biden would do on trade.

To that end, Katie Telford and Brian Clow, the Prime Minister’s chief of staff and her deputy, attended the White House Correspondents’ Association dinner last month, the source said. They spent the weekend at the event’s associated parties gathering information from people close to the presidential contenders.

Around the same time, Mr. Champagne and Ms. Hillman met in Washington with a group of current and former advisers to Mr. Trump. The idea was to open lines of communication with people who could be top players in a future administration, the first Canadian official said.

Ms. Hillman said the conversation included how Canada could help the U.S. limit its exposure to the Chinese economy – such as with minerals and energy – a key theme of Mr. Trump’s campaign. Neither Ms. Hillman nor the sources would specify the Trump-connected attendees of these discreet meetings.

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The first official also described more formal sessions between Mr. Champagne and the Republican governors of Georgia and Nebraska, Brian Kemp and Jim Pillen, in which the governors were surprised to learn how many jobs in their states were tied to Canadian trade. With Mr. Kemp, Mr. Champagne highlighted the role of Canadian critical minerals in supplying Georgia battery plants. With Mr. Pillen, he pointed to investments by Saskatchewan fertilizer giant Nutrien in Nebraska.

Canadian businesses have been doing similar outreach. Last week, the Business Council of Canada brought in Robert Lighthizer for a private event with its members in Calgary. Mr. Lighthizer, Mr. Trump’s former trade representative who negotiated the USMCA, may return to cabinet if his former boss reclaims the White House.

John Dickerman, who runs the Business Council’s office in Washington, said the biggest risk to Canada is getting caught in the crossfire of the U.S.-China trade war. U.S. politicians have long been concerned about Chinese steel and auto parts entering via Canada and Mexico, for instance. “The risk for Canada is becoming the victim of unintended consequences,” Mr. Dickerman said.

The Canadian Chamber of Commerce, meanwhile, has been taking member companies to the U.S. for meetings with legislators and industry.

Matthew Holmes, the chamber’s head of policy and government relations, said the game is showing the U.S. the value of trade when its economy is focused on its large internal market. “We sometimes seem to show up with a list of complaints and irritants without really positioning ourselves as a true partner and ally in trade and security,” he said.

Provincial politicians are also pressing. Alberta Premier Danielle Smith, a conservative, and Manitoba New Democrat Wab Kinew have both visited the U.S. this year.

In a visit to Washington last month, Vic Fedeli, the Economic Development Minister in Ontario’s Progressive Conservative government, nodded to Mr. Trump’s trade deficit concerns. His province’s trade with the U.S. is “almost 50-50 – we are really almost completely equal in terms of what we buy and what we sell,” he said.

David Paterson, Ontario’s representative in Washington, said his pitch is predicated on U.S. self-interest. At a time of concern over inflation it is hard to see the logic of imposing more costs. “The thing about tariffs is that they raise prices locally when you put them in place,” he said.

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