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In his eulogy for George H.W. Bush, Brian Mulroney rhymed off the 41st U.S. president’s achievements: Presiding over the fall of communism, throwing Saddam Hussein out of Kuwait, negotiating NAFTA and clamping down on industrial emissions to end the scourge of acid rain.

What Mr. Mulroney left unsaid was that, in all of these things, he stood at Mr. Bush’s side – sometimes as negotiating partner, often as sounding board, always as ally.

The former prime minister has the rare distinction of eulogizing two American presidents – he also spoke at the funeral of Ronald Reagan in 2004 – in perhaps the most visible reminder of how hard he pushed to bring his country closer to the superpower on its doorstep.

It was a policy decision that paid dividends during his own time in office – and put him in a prime position to help Canada navigate the stormy bilateral seas of the past two years, as President Donald Trump repeatedly threatened to destroy his country’s relationship with its northern neighbour.

“In the life of this country – which is, in my judgment, the greatest democratic republic that God has ever placed on the face of this Earth – no occupant of the Oval Office was more courageous, more principled and more honourable than George Herbert Walker Bush,” Mr. Mulroney told the assembled at the National Cathedral in Washington on Wednesday, offering a definitive embrace both of the man he was eulogizing and the country he led.

When Mr. Mulroney came to power in 1984, Canada had spent the better part of a generation under Pierre Trudeau trying to free itself from its economic dependence on the United States – but still remained reliant on its neighbour to buy the vast majority of its exports.

So Mr. Mulroney changed tack, accepting the trade relationship with Washington and trying to better manage it. As it happened, the prime minister’s policy aligned with that of Mr. Reagan, who was deeply interested in North American integration.

“Reagan wanted to see the continent as a bloc, for the purpose of competing with the Soviet bloc and the Europeans. Mulroney concluded that he had to secure access to the U.S. market,” said Elliot Feldman, a Washington-based trade lawyer who was running a research centre on U.S.-Canada relations at Harvard at the time.

The two men also built a personal rapport, singing When Irish Eyes Are Smiling at the Quebec City Shamrock Summit in March, 1985. Over the following years, their governments negotiated a free-trade agreement, which Mr. Mulroney successfully defended in the 1988 election.

“The cultivation of the relationship was something that Mulroney put a lot of time into,” said Derek Burney, who served as the prime minister’s chief of staff and, later, ambassador to Washington. “He certainly believed that Canada wouldn’t amount to much in the world if we didn’t start by having a good relationship with the United States.”

On Mr. Mulroney’s first trip to the U.S. capital as prime minister, in the fall of 1984, he insisted on meeting privately with Mr. Bush at the vice-presidential residence. Mr. Burney asked why. “You never know,” the prime minister responded.

The move paid off when Mr. Bush became president in 1989; he and Mr. Mulroney enjoyed an even closer relationship than the prime minister had with Mr. Reagan. Mr. Bush agreed to Canada’s long-standing request for an acid-rain treaty, which led to 1991’s Air Quality Agreement. He overruled his own officials to include Canada in the trade negotiations with Mexico that ultimately led to NAFTA. And Mr. Bush consulted the Canadian leader on everything from the Gulf War to the fall of the Soviet Union to dealing with his own Congress. Mr. Bush even used Mr. Mulroney as a go-between with other leaders – having him deliver a message to Soviet chief Mikhail Gorbachev that the United States was serious about seeing German reunification, for instance.

“He used to call me pretty well on a lot of things, and we used to have private lunches and dinners that no one ever knew about,” Mr. Mulroney recalled in an interview.

The two also cultivated a personal relationship: Mr. Mulroney and his family regularly spent time at the Bush summer home in Kennebunkport, Me. On one occasion, Mr. Mulroney recalled his son, Mark, asking Mr. Bush about the action of the ocean and the president taking the nine-year-old out onto the rocks at Walker’s Point to explain the science behind the tides. After leaving office, the pair continued their friendship, taking regular cruises together in the Mediterranean.

Mr. Mulroney kept up with the Americans in his postpolitical life in other ways. His winter home in Palm Beach, Fla., allowed him to cross paths with everyone from Mr. Trump to Wilbur Ross, the billionaire who would become the current President’s commerce secretary. His seat on the board of Blackstone Group acquainted him with chief executive Stephen Schwarzman, who would become head of a business adviser group to Mr. Trump.

All of this came in handy when Prime Minister Justin Trudeau found himself forced to renegotiate NAFTA by the new U.S. President. Mr. Trudeau sought Mr. Mulroney’s counsel on handling Mr. Trump and the negotiations.

Mr. Mulroney also reprised When Irish Eyes Are Smiling in a performance at a cancer fundraiser at Mr. Trump’s Florida mansion during the President’s first month in office; a photograph from the event also showed Mr. Mulroney speaking with Mr. Trump as the latter listened intently. And in January of this year, the former prime minister appeared before the U.S. Senate’s committee on foreign relations to plead the case for free trade.

At Mr. Bush’s funeral, Mr. Mulroney lauded NAFTA as Mr. Trump sat stone-faced a few metres away.

“President Bush was also responsible for the North American free-trade agreement – recently modernized and improved by new administrations – which created the largest and richest free-trade area in the history of the world,” Mr. Mulroney said.

As he lavished praise on Mr. Bush – whom he described as “a true gentleman, a genuine leader” and “distinguished, resolute and brave” – Mr. Mulroney’s words gained an added resonance from the silent presence of the current occupant of the Oval Office.

“The comparisons today are a bit stark – the way Bush carried himself as the leader of the western alliance,” Mr. Burney said.

The same goes for the relationship between the two men: “They had a personal bond I don’t think we’ll see the likes of again at the level of the leaders of our countries.”

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