Will this election be a new beginning — or the end — of Erin O’Toole’s political career?

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This article was published 15/08/2021 (1229 days ago), so information in it may no longer be current.

OTTAWA—When Erin O’Toole’s classmates at Royal Military College wrote his yearbook tribute, they asked: will he ever make it to law school? To Parliament?

The joke back then was it would take a magnet to get the guy out of bed.

But the magnetic pull eventually worked: O’Toole became a lawyer, and made it to Parliament too, first in a 2012 byelection for the riding of Durham, then he became veterans’ affairs minister and almost exactly a year ago, the leader of the federal Conservative party.

Now, he’s facing new questions: with an election called for Sept. 20 will he make it to the prime minister’s job?

And if he can’t, will that be the end of his political career?

That he’s on the path to the prime minister’s office surprises few.

Former RMC classmates say they remember his father, John, a longtime city and provincial Ontario politician, driving up to campus in a car plastered with political signs. It was taken as a given that O’Toole would follow that road.

O’Toole doesn’t frame his jump into politics as following in his father’s footsteps.

Instead, he refers far more often to his days at military college and subsequent time as a navigator on Sea King helicopters as the experiences that led him to take the leap, work he calls an extension of his commitment to a life of public service.

He didn’t always take that approach; when he first sought election in 2012, he told a reporter he didn’t want to be seen as using his career as a springboard.

But today, the website showcasing his biography plays heavily on that theme, a tiny cartoon helicopter whirring readers down paragraphs illustrated by personal photos.

One shows O’Toole standing at attention, in front of a fellow classmate who appears set to give him an order, a photo that gives the impression O’Toole is at the ready to take action.

At the ready he was — to be disciplined for skipping class, his office confirmed to the Star.

He received three days of sanction for the infraction.

A spokesman for O’Toole — he was not available for an interview — said his RMC experiences were formative.

“Mr. O’Toole has always said that RMC helped knock the chip off his shoulder.”

Michael Roach, an RMC classmate in another photo on O’Toole’s website, said O’Toole was an outgoing guy, a natural leader who organized group trips to places like Mexico and Florida.

What Roach remembers most, however, is how O’Toole treated him in basic training.

While the photo shows the two men with wide smiles, in truth Roach was struggling in the program. O’Toole recognized that, and ensured he had support.

“He helped me get through some tough times with a smile,” Roach said.

Some things that characterized O’Toole’s college years appear to have stuck: he was a triathlete, part of the UN club, and active in organizing Remembrance Day events.

Fast forward 25 years: he’s back running, recently issued new policy on international human rights issues, and remains active in veterans’ affairs.

It was due to their mutual interest in supporting Canadian veterans that O’Toole met Shaun Francis some 20 years ago, as the war in Afghanistan raged.

Francis, now the head of an executive medical firm, had studied at the U.S. Naval Academy and got to talking with O’Toole and others about the lack of philanthropic support for Canadian soldiers akin to what existed in the U.S.

Out of those conversations would come the True Patriot Love Foundation, an organization that has gone on to raise significant funds for soldiers.

Francis said he has always believed that O’Toole’s commitment to veterans comes from a place of wanting to do the right thing.

“He didn’t carry himself like, ‘I’m going to be prime minister’,” Francis said in an interview.

“I never thought he had an agenda.”

O’Toole reached the rank of captain in the military, a rank many achieve automatically after hitting certain milestones of service.

Reaching the ranks of federal party leader would take a bit more strategy.

O’Toole took his first run at the top job after Stephen Harper stepped down in 2015, but lost the interim leadership to Rona Ambrose.

In 2017, he tried for the permanent job, running a campaign that was mild in tone and that struggled to get attention in a crowded field of contenders. Nonetheless, he finished third.

His team — which includes people with him since his days as a Conservative backbencher — decided the next time, things would change.

The 2020 leadership candidate O’Toole was an ideological fire-breather, threatening to defund the CBC, take on China’s growing influence, and cancel “cancel culture.”

He forged direct alliances with supporters of the two social conservative candidates in the race, saying he was “true blue” and calling his main rival, Conservative party co-founder Peter MacKay, nothing more than “Liberal-lite.”

It was a far cry from the days of the 2012 byelection when MacKay, then defence minister, campaigned for O’Toole, saying he was thrilled he was running and politics needed more people like him.

O’Toole’s “true blue” persona was met with skepticism by some conservatives and political observers; he’d cut his political teeth volunteering with Progressive Conservatives and had previously been seen as far more aligned with them than the old Reformers he cozied up to during the campaign.

His assumption of a “true blue” mantle was seen by detractors as a way to garner support among the conservative party’s more right-wing factions who’d lined up behind the other candidates.

Asked about that criticism in July 2020, O’Toole told the Star that “with respect, I don’t think you were paying attention.”

O’Toole pointed to a series of previous blog posts opposing “presentism” — judging the past with modern morality — after Trudeau announced his office would no longer carry the name of Hector Langevin, one of the architects of the Indian residential school system.

“I may not have used the term ‘radical left’ (in the 2017 leadership campaign), but that sort of cancel culture, that sort of erasing history, I’ve been talking about for a few years. Everything I’m running on in this campaign I ran on three years ago,” O’Toole said.

Still, the true blue line he walked in the leadership race is becoming more challenging as he now walks towards a general election.

After pledging he’d never introduce a carbon tax, O’Toole went on to do effectively that, much to the chagrin of many Westerners who loathe that federal policy. So far, it’s not delivering what O’Toole promised — a bump in support in Ontario.

Still, Stephanie Kusie — a Calgary MP from one of the bluest ridings in the country — says she sees no real difference between who O’Toole was when he ran for leadership and who he is now.

Admittedly, the carbon plan could have been rolled out better, but it’s the only example of him changing tack that she can think of, she said.

“I’m never wondering ‘Who is this guy?’” Kusie said. “I don’t worry about waking up in the morning to a crazy headline.”

The 2019 election was full of crazy headlines: Liberal Leader Justin Trudeau wearing black and brown face as a younger man, Scheer never completing the requirements to become the insurance broker he said he was, and also holding U.S. citizenship.

O’Toole — says his office — holds only Canadian citizenship.

Headed into the election, O’Toole has struggled though to hold a positive place in the minds of Canadians — 25 per cent in a recent Angus Reid survey think he’d make a good prime minister, and 28 per cent have a favourable viewpoint overall.

His team points to the difficulty of getting known during a pandemic.

Francis said in his experience with O’Toole at veterans’ events he is great in small crowds, coming across as relaxed and confident. Whether he can translate that into making connections in larger groups remains to be seen.

O’Toole’s bigger challenge, Francis suggested, is if he can remain authentic during a campaign and resist the lure of advisers who will tell him to say or do things differently just to win.

“He’s a person doing this out of service, and he wants the country to be more united. He won’t try to exacerbate differences if he can avoid it,” Francis said.

“People might try to push him there, because apparently that works in politics these days. But I don’t think that’s his personality.”

O’Toole has sought to remain grounded, continuing family traditions like weekly drinks around a fire with his wife, Rebecca, getting back into running, and carving out time for his kids Mollie and Jack, and the family dog Wexford.

Wexford’s name is a nod to the O’Toole family’s Irish roots; their first dog was named after the county of Wicklow, where the family is from, so Rebecca and Mollie chose the name of a nearby county for the second pup in tribute to both pieces of the past.

It’s a reflection perhaps of a man many say is rooted in history, and as he gears up for the election of his career, two things may be top of mind.

In the 2004 election, Harper — leader of the newly-formed Conservative party — reduced the Liberals to a minority, though failed to win government.

About a year later, with polls, especially in Quebec seemingly refusing to budge in his favour, calls came for Harper to resign.

He didn’t. Six months after, he won a minority.

In 2019, as the party’s second full-time leader since Harper, Scheer increased the party’s seat count, won the popular vote, and also reduced the Liberals to a minority.

But his failure to bring them down outright also led to calls for his resignation, and he listened, stepping down just a few months later.

Scheer’s move sets a dangerous precedent: the expectation in some party circles is that if O’Toole doesn’t perform at least that well, he’ll have no choice but to quit.

Kusie said it’s too early to say what should or might happen.

“We will have to see where we are after election day,” she said.

“I have not written us off.”

With a file from Alex Boutilier

Stephanie Levitz is an Ottawa-based reporter covering federal politics for the Star. Follow her on Twitter: @StephanieLevitz