The day Donald Trump won the United States presidential election was a happy one for Doug Ford.

The conservative politician who oversees Canada’s most populous province – and its largest economy – made the admission to caucus and supporters, in off-the-cuff remarks accidentally caught by a nearby microphone.

But, Ford said, after Trump announced tariffs on Canada, he was devastated.

“The guy pulled out the knife and fucking yanked it into us,” Ford said. “We’re supposed to be his closest allies, his closest friend. It’s terrible.”

Ford, a blunt-spoken, burly populist with a “limestone head” and a knack for politics, sensed opportunity in the devastation. He called a snap election, telling voters he needed the “largest mandate in Ontario history” to combat an existential threat to the province’s economy. The move was derided as opportunism by other party leaders who accused Ford of “answering chaos by creating more chaos”.

Despised among progressives for the province’s crumbling healthcare system, underfunded schools and a scandal that could have put billions in the pocket of land developers, Ford has now fashioned himself as “Captain Canada” – even leaving the campaign trail twice to lobby leaders in Washington.

Now, as millions of Ontarians prepare to cast their ballot on Thursday for the province’s next leader, the stunning rise of Ford as a dominant political force – not just in Ontario but across the country – has put the 60-year-old populist in uncharted territory.

No Ontario leader has ever won three successive majorities, with each one larger than the last. If Ford accomplishes this, it will reflect a unique political acumen which includes empathy and ruthlessness.

For years Doug toiled in the shadow of his late brother Rob, whose scandal-ridden tenure as mayor of Toronto was notorious for his use of crack cocaine.

When Rob contracted cancer and was unable to continue his mayoral campaign in 2014 it was Doug who ran in his place. He lost, but the bid positioned Doug as the heir to a brash, populist movement that appealed to disaffected suburban voters and affluent, pro-business supporters. After Rob died in 2016, Doug set his sights higher, and in 2018, after a hard-fought race, he was elected to become Ontario’s premier with a commanding legislative majority.

Ford has cultivated a reputation as a leader preoccupied by the daily frustrations of residents. Like Rob, he is famous for handing his phone number out to anyone who asks. During snowstorms, he shovels driveways and helps stranded motorists.

“The thing about Doug Ford is that he really cares about people. And I know every politician supposedly says that, right? That’s cliche, but with him, I truly believe it’s sincere – and he wants to do good things and do right by people,” said Fred DeLorey, a senior adviser for the premier’s 2025 election campaign. “I’ve known him as a political opponent and someone I’ve worked with for years and I can honestly say I’ve never seen anyone like him.”

Ford’s father, Doug Sr, won a seat in the Ontario legislative assembly in the early 1990s, and the family – who run a lucrative label-making business – became a mainstay of conservative politics.

Dave Bidini, the publisher of Toronto’s West End Phoenix newspaper, grew up in Etobicoke, the same Toronto suburb as the Ford family, and says the brothers’ reputation cast a long shadow. “There was a notoriety to a lot of the families in that neighbourhood: a lot of bad behaviour, a lot of wealth, a lot of privilege, lot of early fast cars,” he said.

And, according to reporting from the Globe and Mail in 2013, Doug dealt hashish in the 1980s.

“Most people didn’t approach Doug looking for product. You went to the guys that he supplied,” one former dealer told the Globe. “Because if Doug didn’t know you and trust you, he wouldn’t even roll down his window.”

Ford has repeatedly denied the allegations and his lawyer says the Globe’s reporting is the “height of irresponsible and unprofessional journalism given the gravely serious and specious allegations of substantial criminal conduct”.

Early in his tenure as premier, Ford won praise for his handling of the coronavirus pandemic, following public health messaging – and at times breaking with other conservative leaders. When a report revealed the “horrific” state of the province’s long-term care homes during the crisis, Ford broke down at a press conference as he demanded accountability.

To his critics, however, he governs like a vengeful leader bearing a grudge against Toronto, the city that has never supported him. “People call him a populist but when you look at it, his politics are just so petty and vindictive,” says Bidini.

Ford has repeatedly clashed with residents and activists over plans to remove bike lanes from downtown Toronto, plans for a controversial private spa on public lands, a decision to shutter the city’s beloved science centre, and teacher strikes over class sizes.

Doug Ford at a campaign stop in Milton, Ontario last week. Photograph: Canadian Press/Rex/Shutterstock

“When he was a councillor at city hall, he just caused chaos,” Bidini said. “And I don’t necessarily think that was a strategic move. I just think that that’s just kind of who he is. And you can see that now – a lot of his politics are just trying to see what he can get away with.”

In 2022, Ford found his government embroiled in a deepening scandal over a controversial multibillion-dollar land swap deal.

The plan, which opened 7,400 acres of protected land, dubbed the Greenbelt, for development, would have given windfall profits to developers. The premier eventually reversed course, but the scandal cost him a pair of cabinet ministers, two damning reports from government watchdogs and public outrage.

At a somber press conference, Ford said it was “mistake” to allow development in the green belt around Toronto. “I made a promise to you that I wouldn’t touch the green belt. I broke that promise. And for that, I am very, very sorry,” he told reporters. Canada’s federal police are currently investigating the issue, but Ontario’s ethics commissioner cleared Ford of any wrongdoing.

Still, Ford has largely resisted the partisan nature of modern politics, breaking with other Conservative premiers and cultivating close friendships with key figures in opposing parties like Chrystia Freeland, then federal finance minister.

“Above all, Ford is a pragmatist. He’s clearly intent on achieving and maintaining office. But I do think he has a core commitment to the ‘little guy’ and that really seems to drive a lot of his decisions,” said Andrea Lawlor, an associate professor of political science at McMaster University. The result is a conservative leader able to pull support away from progressive parties and successfully court some union endorsements.

“And in an era of deep political polarization, especially from party leaders, Ford has largely defied that approach. He doesn’t dig in on ideology or wear the partisan stripes. He appears to have sidestepped that.”

With those skills, Ford emerged as one of the strongest pro-Canada voices against the backdrop of a looming trade war, at times drawing praise across the political aisle. He is a fixture of American television news, where he makes the case against possible tariffs.

Ford’s rise fills a perceived vacuum of national leadership, following the resignation of the prime minister, Justin Trudeau, in early January.

Before a high-stakes meeting with Canadian leaders in preparation for American tariffs, Ford, strode into the summit wearing a Maga-style hat with the message: “CANADA IS NOT FOR SALE”.

“We will never be for sale,” Ford told the Guardian last month. “We don’t want to retaliate. We really don’t. But if it comes down to it, [the Americans] are going to feel pain.”

DeLorey, a senior adviser on the campaign, says Ford’s “Captain Canada” branding reflects Ford’s instinct for leadership. “He’s genuinely very concerned about the province, and about where, what the impact tariffs will have on us.”

Bidini, however, described Ford’s latest midwinter election gamble as a calculated move to hold on to power in the face of a wary, demoralized electorate.

“He called this election in the dark depths of winter. People in my neighbourhood don’t even know who’s running because the ground is so frozen you can’t stake a sign in it. The sidewalks are slippery and covered in snow and there it’s bitterly cold out,” he said.

“It’s hard to mount a campaign when you’re up against the elements. It’s the perfect conditions for a person like Ford to get the win that he wants and to perfect his narrative.”