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He’s been a politician’s son, a soldier, a lawyer and a Harper cabinet minister. Today, he may seem like a man out of another time – but his flirtations with Trumpism and right-wing digital warfare suggest a very 21st-century conservatism

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Dave Chan/The Globe and Mail

Even 20 years ago, some of Erin O’Toole’s habits stuck out as old school. He was a Dalhousie law student still in his 20s, but when his new wife, Rebecca, left the table, he stood. The Nova Scotia Tories he was meeting often noticed that after lunch or breakfast with him, he’d send them a handwritten note.

About 10 years ago, James Dodds, the TD Bank vice-president who has just been appointed to head the Conservative Party’s fundraising arm, became so confident his old friend would one day be prime minister that he started keeping the notes, collecting about 40. “It’s a great thing to do, because no one does it any more,” Mr. Dodds said. “They send an e-mail. But a handwritten note, that’s going to get on someone’s desk, no matter how senior they are.”

Smart. And also Mr. O’Toole’s way. Old-fashioned manners were inculcated at home and in four years at Royal Military College. His father, former Ontario MPP John O’Toole, knew to show up for elderly constituents' birthday parties when he was a school trustee and municipal councillor in the 1980s. Erin O’Toole is, in many ways, old school.

He has an affinity for Robert Borden, the First World War prime minister. As a Toronto lawyer, he trooped to meetings of the Churchill Society for the Advancement of Parliamentary Democracy. If he becomes PM, the former helicopter navigator will be the first in more than 50 years with military experience.

But there is a sharper edge. This week, we saw Mr. O’Toole lead his Conservatives in an aggressive parliamentary manoeuvre that, for a moment, brought the country to the brink of a snap election. His party pressed a motion for an “anti-corruption” committee that would not only expand probes into WE Charity but add several new inquiries, issue an unprecedented House of Commons order for PMO e-mails about prorogation and authorize the opposition-controlled committee to summon the Prime Minister or his ministers as it sees fit. It was deemed such a threat by the minority Liberals that they threatened an election if it passed.

It turns out the Erin O’Toole who handwrites genteel thank-yous is not shy about pointy-edged politics. He is both a traditionalist and a practitioner of modern political tactics.

For his party, he is another kind of throwback: the first leader to represent Ontario since George Drew more than 60 years ago. That places Mr. O’Toole, raised in Bowmanville, in the modern battleground of federal politics. He looks like what politicians used to look like: thinning hair, middle-aged spread, suit and tie. He appears older than Prime Minister Justin Trudeau, though he is 13 months younger. “I’m not a celebrity,” he says.

He is deliberately accentuating a contrast. Mr. Trudeau still casts himself as an agent of change, even after five years. In a pandemic, the Liberal Prime Minister has promised to expand social programs and green the economy. Mr. O’Toole talks about Canada building stuff again, selling oil and lumber, keeping statues of Sir John A. Macdonald and a return to normalcy. The old normal.

The tactical Erin O’Toole, however, has flirted with populism and protectionism, even accepting the suggestion that he’s injecting a touch of Donald Trump into Canada. His strategists point instead to lessons from British PM Boris Johnson: When the left campaigns on social justice, they say, Conservatives can win over working people and realign politics – by playing down the ideology of free trade and austerity, and instead talking about protecting jobs and communities.

Certainly, Mr. O’Toole has decided tactics count. Some he knew in Nova Scotia Tory circles 20 years ago marvel that he won the leadership as the more conservative option to Peter MacKay – they thought it was the other way around. In 2003, Mr. O’Toole was a PC leadership delegate for the socially progressive Scott Brison, who later crossed the floor to the Liberals. But Mr. O’Toole repackaged himself with a modern digital campaign, and won with steely tactics.

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At left, Erin O'Toole stands in 1980 with mother Mollie, father John and sisters Marnie, left, and baby Rochelle. At middle, Mr. O'Toole's father and stepmother Peggy attend his Royal Military College graduation in 1995. A year after that, at right, Mr. O'Toole gets his wings in Winnipeg.Family handouts

“I’m Erin O’Toole, from Bowmanville, Ontario.”

The new Conservative Leader has taken to introducing himself with his home town. When Mr. O’Toole’s parents moved in 1974 so that his father, John, could take a manager’s job at the nearby GM factory in Oshawa, Bowmanville was a small town in mostly white, staid Ontario. Now, the GO Train is supposed to be coming soon to serve its commuters.

The young Erin O’Toole really did have a middle-class upbringing in middle Ontario, playing Kenickie in the high-school production of Grease and competing on the swim team. The other part of Mr. O’Toole’s folksy introduction, the suggestion that he grew up a long way from politics, omits the fact that his political career is no accident.

Mr. O’Toole’s sister Rochelle Trainor said her cousins recounted a childhood conversation about what they, and Erin, would be when they grew up. “They were like, ‘Oh, I’m going to be an NHL star.’ When they asked Erin, he said, ‘I’m going to be prime minister.’ ”

In Erin O’Toole’s teens, his father was always getting elected, first as a school-board trustee, then a municipal and regional councillor. Though John O’Toole’s 19 years in the Ontario Legislature began after Erin left for military college, the son saw plenty of how politics was done in Durham, a riding of auto workers, suburbanites and small-town folks. John O’Toole rarely made big headlines – he was caught flipping the bird in the legislature once, and campaigned to bar drivers from using cellphones – but he worked the constituency. “He did retail politics very well – I grant him that,” said Granville Anderson, a regional councillor and former Liberal MPP who succeeded John O’Toole. “He goes to every single thing in the community. The 90th birthday party, the 100th birthday party, every community event, the community fairs.”

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Erin O'Toole, middle, smiles with swimming teammates Greg Wells and Mike Meyers in 1981.Family handout

To Rochelle, six years younger, Erin was the upbeat big brother in a family that emerged through tragedy. Their mother, Mollie, died when Erin was 9, after a long illness. It was Erin who made a point of preserving the memory of Mollie for Rochelle and middle sister Marnie, and remained positive through a strong will, Rochelle said. “I think a lot of that has come from seeing the strength of our dad to move on with three young kids at home.”

It was eventually five kids. John O’Toole remarried, to Peggy, the ex-wife of his brother Jerry. “I think it was just over the years of supporting each other through difficult times that they ended up connecting,” Ms. Trainor said. “Obviously it was, I guess, weird for the rest of the family. But it all has worked out, oddly enough.” Peggy became mom – not stepmother – the mom who taught her kids to send notes of appreciation. Her two children became sister and brother to Erin, Marnie and Rochelle.

The teenaged Erin O’Toole liked eighties Britpop – the Smiths, Depeche Mode – but didn’t sink into the downbeat mood of the lyrics. By the time he graduated, Ms. Trainor said, he was ready to get away on an adventure, but also wanted the structure of a path laid out for him.

He signed up for Royal Military College, and boarded a plane to Chilliwack, B.C., for seven weeks of basic training. Then it was back to Kingston for recruit term: up at 5:30 a.m. for a five-kilometre run, into class, then out for sports. A cadet’s schedule was plotted out until 10 or 10:30 at night, said Derron Bain, a former RMC classmate. And it was always underpinned with the culture of the military college.

“To really understand Erin, and who he is, and his values, you don’t need to look much further than the RMC experience, and really, the ethos of the military,” said Mr. Bain, now a friend of 29 years. “The RMC motto is Truth, Duty, Valour. That’s instilled in us from Day 1 when we arrive at the school.”

First-year cadets wore the uniform off campus. Second-year cadets were given a blue blazer, gray slacks and tie. In town, Queen’s University kids could spot them a mile away. For RMC students, most socializing was “mess life,” the on-campus downtime from regimentation. Mr. O’Toole played rugby, did a few triathlons, made friends and did well in political science and economics, Mr. Bain recalled. He leaned to politics.

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Mr. O'Toole takes part in training exercises in Puerto Rico.Family handout

As an Air Force officer, Mr. O’Toole served in a peacetime military, in the regular force from 1995 to 2000, before 9/11, before Afghanistan. “He jokes that he had a mediocre military career,” said Mr. O’Toole’s long-time senior aide, Tausha Michaud. After a stint in Trenton and flight training in Winnipeg, he was posted to Halifax, as a navigator in the aging CH-124 Sea King helicopters.

It was still serious business. Sea King navigators are trained to co-ordinate anti-submarine tactics. For a time, Mr. O’Toole’s helicopter crew served the frigate HMCS St. John’s, sailing the Atlantic and Caribbean. He worked co-ordinating the hangar in Trenton when it became the de facto morgue during the grim task of recovering bodies from the 1998 Swiss Air crash near Peggy’s Cove, N.S., that killed 229.

It was in Halifax, not Bowmanville, where Mr. O’Toole really cut his own teeth in politics. He volunteered for then-leader Jean Charest’s moribund PC party, then on Nova Scotia Tory leader John Hamm’s successful 1999 campaign, compiling briefing books for the leader’s tour. Mr. Bain, who had become his neighbour, introduced him to Mr. Hamm’s executive assistant – soon to be Mr. O’Toole’s wife, Rebecca. He moved from regular forces to the reserves and Dalhousie law.

In 2003, he moved back to Ontario to practise law, articling at Stikeman Elliott, then working as in-house counsel for household-brands giant Procter & Gamble. His stint at Heenan Blaikie in Toronto is how he put “Bay Street lawyer” on his résumé, but he wasn’t really high-powered: He was an employee, not a partner, and Mr. O’Toole, by then father to Mollie and Jack, lived the life of a commuter dad.

There was something else: He got involved in things, and had a knack for making lasting connections. Mr. Dodds, a friend from Nova Scotia Tory circles, moved to Toronto, and Mr. O’Toole organized a networking lunch at the Conservative establishment Albany Club. He got to know Joel Watson, a Heenan Blaikie colleague – and later aide – at Churchill Society meetings and veterans' charity events. Ms. Michaud was given responsibility on his first campaign, at 26, and became his right hand.

By 2012, when Durham MP and Conservative minister Bev Oda quit after an expense-account controversy, his friends texted each other the same question, Ms. Michaud said: “Is this Erin’s time?”

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Prime minister Stephen Harper shakes hands with veterans' affairs minister Julian Fantino in 2013.Peter Power/The Globe and Mail

The by-election was a relative cakewalk. But Stephen Harper’s third term wasn’t. Then-veterans affairs minister Julian Fantino had fumbled the file and the Conservatives pro-military brand, snapping at a decorated veteran. Mr. O’Toole, a highly regarded rookie MP, was platooned onto TV panels to defend the Tory record. “He stuck out as a really solid communicator,” said James Moore, then the industry minister.

There was little surprise when Mr. Fantino was shuffled out 10 months before an election, and Mr. O’Toole succeeded him. He walked into Mr. Harper’s office with a plan.

A group of injured Afghanistan vets had launched the Equitas case, a lawsuit claiming their pensions were a fraction of older vets. It was a politically damaging case. Mr. O’Toole, himself a lawyer, planned to negotiate – and to take the case out of the hands of government lawyers.

The Justice Department lawyers hadn’t helped the politics. They had filed a defence case asserting that the government had no special duty of care to injured veterans. “There was no way we were going to negotiate with these guys,” said Mark Campbell, a plaintiff and retired major who lost his legs in Afghanistan.

Mr. O’Toole brought in his friend Mr. Watson, also a veteran, to supervise the Justice Department lawyers. They negotiated a deal to put the case in abeyance. Mr. O’Toole, who had co-founded a veterans’ organization, True Patriot Love, agonized over revamping programs. “He took it home with him,” Ms. Michaud said.

The government rolled out some new benefits; Mr. Campbell figured the prime minister would never give Mr. O’Toole funding for a full reform. “I told him across the table I didn’t think he had the juice,” Mr. Campbell said.

The Conservatives lost power that fall, and the Equitas plaintiffs later lost their case. Some veterans' activists thought they were played. Mr. Campbell, however, endorsed Mr. O’Toole in 2015. “Erin never promised anything he could not deliver,” he said.

Politically, Mr. O’Toole had controlled the damage. “He sort of tamed a brushfire,” Mr. Moore said.

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Mr. O'Toole, then the veterans' affairs minister, gives a speech at the Defence Department's Ottawa headquarters in May, 2015. A few months later the Conservative goverment would be defeated in an election.Adrian Wyld/The Canadian Press

The defeat of the Conservatives led to a name game of possible successors – Peter MacKay, Jason Kenney. Mr. O’Toole’s was barely an addendum. He’d been a cabinet minister for all of 10 months. But he saw himself in leadership.

He ran first for the party’s interim leadership, and lost to Rona Ambrose. When the biggest names balked at running for the permanent leadership, he started preparing his own bid. Even in a field of Maxime Bernier, Lisa Raitt, et al, he acknowledged he was an unknown.

He sold himself as a leader who didn’t have baggage from the Harper era. He also didn’t have much of a political identity. He ran as a capable compromise, and finished a distant third.

The loss hurt. “I think it was a lot of self-reflection,” said Mr. O’Toole’s sister, Ms. Trainor.

When the Conservatives lost another election in 2019, Mr. O’Toole was ready to run again. But he knew he’d need a sharper, more forceful campaign in 2020. Still, the first plan was to run as a unity candidate. Peter MacKay was seen as the Red Tory. Ottawa MP Pierre Poilievre was expected to stake out the right. But when Mr. Poilievre dropped out on Jan. 23, Mr. O’Toole’s team seized his terrain.

Four days later, Mr. O’Toole launched his campaign with a video telling party members that their choice was between a party “more like the Liberals,” or one that would “take a principled conservative stand.”

It wasn’t really about policy. Mr. O’Toole’s platform, when it came out months later, wasn’t a sea change from the manifesto he wrote in 2017 – updated for a pandemic, and measures targeted to elements of the party base. This was a tactical shift.

Mr. O’Toole’s team didn’t want to fight the better-known Mr. MacKay on who could beat Justin Trudeau. It would campaign on who reflected party members' conservative values. Mr. O’Toole got it, and worked on it.

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Mr. O'Toole and leadership rival Peter MacKay wait for the start of the French-language leadership debate in Toronto this past June.Frank Gunn/The Canadian Press

One tactic was to make social conservatives feel heard. Mr. MacKay had offended by saying Andrew Scheer’s social conservatism "hung around [his] neck like a stinking albatross.” Mr. O’Toole didn’t promise to ban abortion, but said he’d allow health care workers to refuse to refer women for the procedure. He told social conservatives he’d defend their right to express their views.

More than anything, Mr. O’Toole rang bells with the base by running as a cultural conservative – criticizing the removal of statues of historical figures as “cancel culture,” complaining about Indigenous rail blockades and promising to be tough with China.

The newly tailored identity was branded with digital tools: brightly coloured memes and tendentious videos.

Jeff Ballingall, creator of conservative Facebook pages Ontario Proud and Canada Proud, headed digital strategy. The O’Toole Facebook page was amplified by the “Proud” pages and more than a hundred “digital activists” co-ordinated in a WhatsApp group. One video, labelled “What Justin Trudeau and the Chinese Regime Aren’t Telling You About COVID-19,” had 1.2 million views.

Mr. MacKay was mocked as hapless. Memes lumped him side by side with Mr. Trudeau as a Liberal.

A key ally was The Post Millennial, a conservative site – in which Mr. Ballingall owns a small stake – that promoted Mr. O’Toole the way U.S. site Breitbart had hyped Mr. Trump in 2016. One Post Millennial story on a “leaked” O’Toole campaign poll quoted a polling firm calling Mr. MacKay’s campaign a “disaster,” without mentioning the the firm was run by Mr. O’Toole’s campaign manager. Mr. MacKay’s campaign made it worse by threatening to sue.

In the end, Mr. O’Toole’s win was clinched by two things: recruiting gun advocates to vote in nearly vacant Quebec ridings, and winning second- and third-ballot votes from supporters of social conservatives Leslyn Lewis and Derek Sloan.

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Mr. O'Toole, wife Rebecca and children Mollie and Jack walk to the stage at the Conservative leadership election night in August.DAVE CHAN/AFP via Getty Images

When the new leader took the stage at 1:30 a.m. on Monday, Aug. 24 for a delayed victory speech, he was already executing a tactical pivot. He emphasized unity. On the Tuesday, at his first press conference, he distanced himself from social conservatives, bluntly identifying himself as pro-choice.

In his second week, he shed the burden of balanced budgets, telling The Globe and Mail that he would balance the budget in “a decade or so.” That leaves more leeway for election promises. He reached out to new Canadians in the 905 by embracing family reunification immigration.

He isn’t sullen like Stephen Harper, or guarded like Andrew Scheer. Mr. O’Toole smiles, mimics accents, has a lawyer’s love of a good argument and writes his own wonkish policy. He relates his mother’s passing with teary-eyed emotion. And he has a bit of ruthlessness.

In just weeks as leader, he has signalled where he is going.

Look at his Labour Day video, where he reached out to unionized auto workers and resource workers, complaining that their sectors are losing jobs because of government policies, but also because of profiteering big business, China and bad trade deals.

That’s a tactical shift from Harper-era ideology in an effort to realign politics by winning working voters – and the old-school Mr. O’Toole is promising to protect the jobs, and the Canada, they have known.

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