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Federal NDP leadership candidate Jagmeet Singh, expected to be the front-runner of the race, is convinced of his ability to win.Dave Chan/The Globe and Mail

This piece was originally published on Sept. 22, 2017. On Oct. 1, Jagmeet Singh was chosen as the new leader of the federal NDP.

"I happen to be younger, cooler and better-dressed, so actually it's not fighting fire with fire…"

Jagmeet Singh trailed off. He was responding to a question about concerns from other New Democrats that he shares too much of Justin Trudeau's flash to strike the right contrast with him. "It's fighting … I can't think of something hotter than fire, with something less hot than fire."

Fatigue had him a bit off his game. We'd been talking for almost an hour, at the end of a long campaign day, in the final weeks of a leadership race that has him travelling to parts of the country he's never been before. That day's stop was in the small British Columbia city of Merritt, where he'd just held a question-and-answer session with about 30 locals.

But with the first part of his comparison to Mr. Trudeau, he's already offered a window into what makes him so disruptive to the party's establishment and so thrilling to some New Democrats – including the tens of thousands of new members he signed up. The support has helped make him the expected front-runner in the NDP's first round of leadership voting, the results of which will be announced on Oct. 1.

Since the erstwhile deputy leader of the Ontario New Democrats entered the national race in May, and especially since video of him deftly handling an Islamophobic heckler garnered international attention earlier this month, Mr. Singh's unusual proposition to the NDP has sometimes been reduced to his Sikhism. (The heckler may have mistaken him for a Muslim.) But there is much more that would set him apart from past NDP leaders than just the colour of his skin and the turban on his head.

In a party that has traditionally focused on substance over style, frowned upon leaders' personalities or value sets overshadowing their adherence to party dogma and expected them to speak first and foremost to other New Democrats before soliciting outside support, Mr. Singh promises a culture change his three opponents do not.

Certainly, he is not playing down that being Canada's first visible-minority leader of a major national party would be a big part of that development. Even when speaking to predominantly white crowds in places such as the B.C. Interior, he devotes much of his introductory remarks to recalling discrimination he faced growing up in Ontario. His appeal is partly predicated on being able to crack into immigrant-heavy suburbs which have long rejected the NDP, and where he has twice in a row won a provincial seat. When New Democrats fret whether the rest of the electorate is ready for someone who looks like him – a frequent question, given polls showing Quebeckers in particular having serious trouble with it – he pushes back hard.

"Instead of asking if Canada is ready, I would say Canada needs this," he told an elderly white woman in Merritt who cited prejudice in her own community. "Nobody thought America was ready for Obama, but America needed Obama."

But with that rather bold comparison, Mr. Singh again demonstrated that he is a candidate defined as much as anything else by a level of confidence that veers into brashness.

It might be an armour that he developed in response to racist bullying while growing up in Windsor, Ont. The implication explains the persona he's built for himself, one that has him fight competitively in mixed-martial arts and cut a striking figure in expensive suits while driving his sports car or riding his bespoke bicycle. "Nothing is natural," he said in the interview. "Everything is your life experiences … I think I've honed it over the years."

However he came by it, his swagger informs his willingness to break unwritten rules about how to campaign for an NDP leadership and – if he wins – about how to run the party.

He has all but admitted during the campaign that he's already looking past the race. "I won't lose," he repeatedly replied during one of the campaign's final debates, when rival Charlie Angus pressed him on whether he would seek a federal seat regardless of the outcome. He is so confident about victory that, members of his campaign team say, he has consciously fashioned his messaging to appeal to the broader electorate.

After the win he is expecting, he intends to spend as much time as possible outside Ottawa. While Tom Mulcair made holding the government to account in Parliament the focal point of his leadership, Mr. Singh has indicated he might not even seek a seat there until the 2019 general election, in the hopes of focusing on broader outreach.

And while the messaging during that outreach wouldn't be at odds with party tradition, it might not be terribly familiar, either.

Provincially, Mr. Singh has steered his party onto policy turf where it otherwise would not have tread. New Democrats at Queen's Park, where he is the only non-white member of a 20-person caucus, credit him as not just the public face but the driving force behind the NDP's opposition to police carding, which resulted in Ontario's legislature passing a motion to that effect. And he has proved an enormously effective advocate on other issues, such as auto-insurance rates disproportionately high for certain demographics, which appeal to his sense of fairness.

He has spoken to a much broader range of issues during the leadership, with a detailed platform diving into matters such as income security. But it's where he sees injustice that the former criminal-defence lawyer tends to be most persuasive. Asked which federal issues get him most excited, one of the two he settled on was "criminal-justice reform, shifting from a punitive to a rehabilitative model," including decriminalization of all drugs for personal use. (The other, expanding health-care universality via pharmacare, was more standard NDP fare.)

If his priorities would be new, the way he communicates them – in the language of millennials, even if at 38 he is slightly too old to qualify as one himself – might be more so. When he introduces himself to audiences, he does not follow the typical politician's template – jokes up front, policy promises or critiques in the middle, close with a call to arms. In language peppered with "like" and "literally," he personalizes his values by sharing his own experiences. The longest of his go-to stories, relating to carding, is about being harassed by police while visiting Toronto's Casa Loma – a tale he physically acts out and plays for laughs.

"Hopefully I put on a good show, you had a good time, some good laughs," he said in Merritt before taking questions. Sometimes he'll invite his audience to gather around him so he can shoot a Snapchat video, part of a social-media strategy alien to party stalwarts.

Not that there is likely to be a surfeit of such veterans behind the scenes in Ottawa, if he wins. Mr. Singh is not averse to links with his party's past – his campaign manager, Michal Hay, was plucked from the office of Jack Layton's city councillor son – but he avoided giving many backroom hold-overs from the Layton and Mulcair eras official campaign roles.

The NDP, Mr. Singh said, has for too long been resistant to "new organizers" inclined to take "bold chances." He wants to bring in a younger crowd, more diverse and less steeped in the party's Byzantine inner workings.

An overhaul by a charismatic Toronto-area politician lacking federal experience would not be totally unprecedented. In response to New Democrats who consider Mr. Singh an interloper, his supporters point out Jack Layton faced similar pushback when he became leader in 2003. But that undersells both the freshness of Mr. Singh's offer to the NDP and the leap of faith he is asking it to take.

The son of an MP, Mr. Layton spent most of his adult life establishing himself as the standard-bearer for Toronto's left, through more than two decades on city council and a mayoral campaign. Mr. Singh has spent six years in politics, coming to it by way of social activism. His outsider credentials are more real, but his learning curve is more steep.

As impressive as he is at smaller events, he has underwhelmed on some of the bigger stages, including candidates' debates. He suggests that's because he's struggled to argue with people he mostly agrees with and agrees with the assessment of people close to him that despite his much-noted MMA expertise, he's not confrontational by nature. A couple of trusted advisers also offered another explanation. Mr. Singh had rarely, if ever, delivered a prepared text until his stilted campaign-launch performance. His natural style is so conversational that he frequently apologizes for being long-winded, during public appearances and interviews. As he now finds himself on platforms that require him to get points across succinctly, he is trying to find the right balance between being authentic and leader-like.

He has also not looked altogether at ease with some sensitive policy files – taking longer than other candidates to find his footing on the Kinder Morgan pipeline, which pits Alberta New Democrats against the rest of their party. (He eventually joined the rest of the field in opposing the project.) While he has appeared more comfortable as the campaign has worn on, his knowledge of federal fiscal management or program delivery can still seem a bit thin compared to rivals who have spent more of their careers thinking about such things.

And there are questions about how he would manage a federal caucus, not just because he would not initially have a seat. He is generally well-liked by provincial colleagues, about half of whom endorsed him, but has been known for playing a bit by his own rules – an MPP who leads on his issues but doesn't always show up for House duty. Especially if most of his staff is also new to Ottawa, discipline could be an issue.

Mr. Singh does not dispute that he's a work in progress; if anything he takes pride in it. He considers himself a quick study and a good listener. Those who have interacted with him during his provincial career agree he's not afraid to admit what he doesn't know, and welcome advice.

But for a party that has been in a funk since the rare whiff of power before the federal election became a return to third place, it's not humility that helps makes his case. It's the aplomb that has him looking at Canada's celebrity prime minister and thinking he can take him on his own terms.

Mr. Singh has been claiming new ground for the NDP since he got into politics. And if there is one thing he visibly can't stand, it's doubt from fellow New Democrats about his ability to back up his talk with action.

During the Q&A session in Merritt, a local activist persistently expressed skepticism about shifting jobs from fossil fuels to renewable energy, one of Mr. Singh's more NDP-standard and aspirational campaign commitments. He'd been hearing the same thing forever, the activist kept saying, and interests aligned against it kept proving too powerful.

"That's life, man – we're going to deal with it," Mr. Singh finally shot back. "Bring it on."