NDP’s Jagmeet Singh responds with unsinkable optimism in a campaign weighed down by the politics of race

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The moment he heard the word “brownface,” Jagmeet Singh blinked, hard.

This was supposed to be a routine campaign stop: a town hall with 100 or so NDP supporters in northern Toronto. Around 7 p.m., Mr. Singh began taking questions from the audience. That’s when a reporter stepped up to the microphone and broke the news: a racist photo of Justin Trudeau had emerged.

Behind Mr. Singh stood a handful of supporters, and the shock of the news played out on their faces. A young black woman looked visibly disturbed. The South Asian man next to her mouthed something that looked like “Oh my God.”

But Mr. Singh remained still. “Racism is real,” he said. The expression on his face wasn’t one of anger or frustration – more like resignation.

A couple of hours later, after he’d seen the photos of Mr. Trudeau with his face painted brown and a cartoonish turban on his head, Mr. Singh stood in front of a pair of beige curtains inside a dimly lit airport hotel room, staring into a camera. “I want to talk to all the kids out there, all the folks that lived this, who are now grown up and still feeling the pain of racism,” Mr. Singh said. He was wearing the same robin’s-egg blue turban and white button-up shirt from earlier that evening. “I want you to know that you have value, you have worth, and you are loved.”

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Mr. Singh’s reaction, which came just a week into the election campaign, was reminiscent of another moment, shortly before the NDP leadership vote in 2017, when a woman interrupted a Brampton event shouting about “sharia” and the “Muslim brotherhood.” Mr. Singh was lauded for his calm demeanour throughout the encounter, and the resultant celebrity helped him win on the first ballot in October, 2017.

Back then, he was hailed as a breath of fresh air. This was after five years of Tom Mulcair, who led the NDP to a rout in 2015, dropping to 44 seats from 103. Mr. Singh was young and flamboyant, and had amassed a huge following on social media (as of this week, he can count among his Instagram followers Drake and Rihanna). He connected with young people – particularly young people of colour – and promised, after the centrist Mulcair years, to nudge the party back toward its NDP roots.

But in the lead-up to the federal campaign, the movement many expected Mr. Singh to build had not materialized.

Several high-profile members of Parliament, including Nathan Cullen and Murray Rankin, decided not to run again. Fundraising plunged (in the second quarter, the NDP pulled in just $1.4-million, roughly even with the Greens) and party divisions endured.

Much of the disarray was of Mr. Singh’s own making. He had no experience on a national campaign and brought along a team from his time as an Ontario MPP in Brampton that lacked the institutional knowledge needed in Ottawa. Caucus members second-guessed him. And under the national spotlight, the candidate himself stumbled repeatedly. For a man who had found success in just about everything he’d tried, Mr. Singh appeared unsteady, unprepared and, in his worst moments, uninterested. With the weight of expectations on his shoulders – as the first racialized person to run for the country’s highest office – each of his stumbles felt seismic.

Four weeks into the campaign, polls put the NDP in distant third. But the brownface scandal seems to have been a turning point for Mr. Singh. Once again, he received widespread praise for “rising above” the incident, and in the weeks since, he has gained momentum.

On the campaign trail, he has looked comfortable and confident. Last week saw one of Mr. Singh’s sharpest moments, when he turned the tables on a reporter during an exchange over providing access to drinking water in First Nations communities. “Why is that even a question?” he asked.

But no matter what Mr. Singh does, the conversation keeps coming back to the colour of his skin. Just last week, hours before the French-language debate in Montreal, an older man pulled him aside while he campaigned in Atwater Market. “You should cut your turban off,” the man told Mr. Singh. “You’ll look more like a Canadian.”

Mr. Singh responded with what has become his customary grace. But it’s not just his performance that is under the microscope here. The treatment he has received during this campaign has laid bare an ugly truth about our country: that Canada has much farther to go in terms of truly embracing diversity. That’s the reason Mr. Singh has to answer the same question over and over again, a question none of his opponents has ever had to contemplate: “Is Canada ready for a prime minister who looks like you?”

Setting aside the fact that Canadians have never elected an NDP government, Mr. Singh says the answer is yes. But with an election less than two weeks away, it’s not clear even he believes it.

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The party Mr. Singh inherited in 2017 bore little resemblance to the NDP under Ed Broadbent, or even under Jack Layton. That was the party built on social democratic principles, that believed in equality and the importance of a strong welfare state above all else.

But when Mr. Layton died in August, 2011, three months after leading the party to official opposition status, Mr. Mulcair became leader and started pulling the NDP toward the centre, just as the Liberals were elbowing their way further to the left. As a result, the 2015 election saw an awkward role reversal, with the Liberals promising years of deficits, while the NDP pledged surpluses and a clampdown on spending. Not surprisingly, the NDP lost almost all the ground it had gained in 2011 to the Liberals.

This time around, the Liberals are holding on to many of their centre-left positions, leaving Mr. Singh to carve out territory even further to the left. On climate change, he has pledged to spend $15-billion in part to cut emissions by 38 per cent below 2005 levels by 2030, compared with Mr. Trudeau’s promise for “net zero emissions” by 2050. To tackle income inequity, he has said he would reinstate a federal minimum wage, at $15 an hour, and build more affordable housing.

To pay for it all, Mr. Singh will increase corporate taxes and create a new 1-per-cent tax on the “super rich." As for when he might balance the budget – a cause near and dear to Mr. Mulcair’s heart – Mr. Singh won’t make any promises, except to say that the NDP would do so “when prudent.”

All of this was supposed to draw clear lines between the NDP and the Liberals. It might not be enough. One of the NDP’s key planks would see it dedicate $10-billion a year to extend prescription drug coverage to all Canadians, and to fold dental, mental health and eye care into the public system. But the Liberal campaign has promised pharmacare, too (though they’ve only pledged a $6-billion “down payment"). The incumbents have also echoed an NDP pledge to lower cellphone and internet rates.

On issues where Mr. Singh clearly opposes the Liberals, he has struggled to articulate his own positions. In the past, he has stood firmly against the Trans Mountain project, which would run through his home riding of Burnaby, B.C., many of whose residents are fiercely opposed to the development. When it comes to the question of future pipelines – whether he would grant provincial vetoes and how he would engage with Indigenous communities over the projects – he has failed to make his position clear.

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The policies he seems most comfortable talking about are traditional NDP ones that would have helped him in his own early years.

Mr. Singh was born in Scarborough in 1979, to parents who were recent immigrants from Punjab, the heart of India’s Sikh community. By the time Jimmy, as Mr. Singh was then known, was in second grade, his father was a practising psychiatrist in Windsor, Ont., who paid for martial arts lessons and private school. He also emphasized the importance of dressing well as a kind of “social armour” in the predominantly white city. “As people of colour, we couldn’t afford not to look good,” Mr. Singh wrote in his recent memoirs, Love and Courage. “He wanted to make sure we never felt the way he did: like we didn’t belong.”

At the age of 8, Mr. Singh – who spent weekends serving meals with his mother at the local gurdwara – decided to revert to his birth name. He also decided to grow out his hair and began wearing a patka, the piece of cloth worn by boys to cover their emerging top knot. Eventually, he would trade in the patka for a turban and kirpan.

At school, Jagmeet was laughed at, beaten, and called names such as “diaper head” and “Paki.” That was only part of his torment. In his memoirs, he says he was sexually abused by a martial arts instructor, which he only disclosed to friends and family more than a decade later. The experience, he wrote, left him feeling “dirty” and “like I didn’t deserve love.”

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At home, meanwhile, the family’s middle-class dream was coming apart. The elder Mr. Singh began drinking heavily, and over the next decade, he lost his medical licence and the family home, and had to file for bankruptcy. When Mr. Singh was in his second year at the University of Western Ontario in London, Ont., he brought his 15-year-old brother, Gurratan, to live with him, fearing for his safety.

The years he spent as a student working part-time retail jobs to feed himself and his brother gave him insight into how precariously many Canadians live. And dealing with his father’s addiction and recovery reinforced the importance of public institutions.

Similarly, the values he’d first learned from his faith – the values that lie at the core of the NDP – were ones he watched play out in his own life: community service, sharing of wealth and advocating on behalf of the marginalized.

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The fall of 1984 was a seminal time for the Sikh community. That October, Indira Gandhi was assassinated by her Sikh bodyguards, igniting a wave of anti-Sikh violence that left between 3,000 and 17,000 dead across India. A year later, a Sikh extremist group bombed Air India flight 182, killing 329 people, most of them Canadians.

It was a painful series of events that sowed deep divisions between Hindus and Sikhs, and Mr. Singh grew up watching the trauma ripple through his community. As a young criminal defence lawyer, he began organizing “know your rights” seminars to teach students how to deal with race-based profiling. The seminars were hosted by the Sikh Activist Network, a community of young people created by Mr. Singh’s younger brother, Gurratan, and his long-time friend Amneet Singh. The group’s arts showcases drew thousands of young people and served as an incubator for local talent, including bestselling poet Rupi Kaur.

A turning point for the young activists came in 2010, when two Liberal MPs circulated a petition to formally recognize the 1984 violence against Sikhs as a genocide. For decades, the Liberals had been the de facto party for many immigrant groups. But then Liberal leader Michael Ignatieff refused to support the petition and accused the groups of being “polarizing.”

Gurratan encouraged Mr. Singh to take a run at politics as part of the NDP, whose new leader, Jack Layton, had supported the petition. Mr. Singh travelled to Ottawa to meet with Mr. Layton, who reinforced his decision to run. He lost his first campaign, in Bramalea-Gore-Malton, in 2011, but later that year, ran for the provincial NDP in the same area. This time, he won.

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His earlier work with the Sikh Activist Network made him a controversial figure. “There’s a divide in the South Asian community,” says Rupinder Kaur, who worked for both Mr. Layton and Mr. Singh. “Some are still very connected and loyal to their Indian roots. Those ‘pro-India’ people may be uncomfortable or unsupportive of Mr. Singh’s activism against India, especially on human-rights issues.”

Still, he owes much of his early success to that activism. The “know your rights” seminars won him a huge following of young people. He also created a community space at his constituency office where they could hang out and host events. Many of these same people would go on to become campaign volunteers and organizers.

In 2016, when his brother (who remains a close adviser) and others urged him to run for the federal leadership, Mr. Singh was wary. He was already deputy leader of the Ontario NDP, and he was hoping for an NDP victory in 2018 that might lead to an appointment as attorney-general. Nonetheless, his supporters put out feelers to determine Mr. Singh’s viability as a candidate. What they heard was that Mr. Singh represented a fresh face supporters might get excited about.

His campaign focused on four planks – climate change, inequality, reconciliation and electoral reform – that represented a pivot back to the left. He won in the first round, with 53 per cent of the vote.

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On an unusually humid August afternoon in New Westminster, B.C., Mr. Singh was looking for a quiet place to sit. He was at a farmer’s market and the air smelled of baked strawberries. He’d just wrapped up a scrum in front of glum-faced TV camera operators, railing against Mr. Trudeau “protecting the very wealthy and powerful,” while wearing a Rolex watch and $60 T-shirt.

Deeper in the park, there were picnic tables and park benches. But Mr. Singh decided he wanted to sit right there, on the grass. “I’m a grass person,” he said. He was wearing tightly fitted jeans, and the grass stuck to his bare ankles. But he looked perfectly pleased, stretching out his legs and setting his palms down behind him.

He speaks in a soothing, surfer-dude tone (he does, in fact, surf ). His sentences are frequently punctuated with millennial slang – it’s never “yes,” but “100 per cent”; not “good,” but “awesome.” His assessment of two dogs at the market earlier: “they seem pretty chill.”

As he spoke about this park and its proximity to his Burnaby riding – about how he’d like to raise a family there with his wife, fashion designer and Instagram-influencer Gurkiran – he did so with an earnestness that seemed completely genuine.

But the illusion came apart moments later, when he turned his focus to Mr. Layton. “He was really humble,” he said, gesturing at the grass and the park around us. Suddenly, his insistence on sitting on the ground seemed like political artifice. Mr. Layton was, after all, the kind of politician people wanted to have a beer with – the kind of guy who would have insisted on sitting cross-legged on the grass. “Really down to earth,” he repeated.

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Another comparison Mr. Singh wanted to draw between himself and Mr. Layton: the late leader told everyone he was in it to win. That was a major shift for the NDP, to see itself as a party that might wield real power.

Now, Mr. Singh says he too is running to become prime minister.

It’s an audacious claim and one that will be difficult to deliver on. Since taking on the leadership, Mr. Singh has failed to unite the party. Some of it has been outside his control. Mr. Layton’s success permanently raised expectations. And after Mr. Mulcair’s ouster, with the party millions of dollars in debt, a number of high-profile NDP figures passed on the idea of taking the reins.

His first months as leader were dimmed by criticism from his own caucus. MPs publicly second-guessed his decisions (most notably around kicking out Saskatchewan MP Erin Weir after a sexual harassment investigation). Even Mr. Mulcair has weighed in – unprecedented behaviour for a former leader – criticizing Mr. Singh for waiting almost 18 months before running for a seat in the House. (It was only under intense pressure from his own caucus that Mr. Singh finally ran in Burnaby South.) After Monday’s chaotic televised debate, it was nearly impossible to declare a winner. Mr. Singh was singled out for rising above the fray by some pundits, although Mr. Mulcair proclaimed Mr. Trudeau and Mr. Scheer to be the winners.

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Mr. Singh hasn’t done himself any favours. Former staffers and advisers say he was unprepared for how different Ottawa would be from Queen’s Park. Some of the young people he’d trained in his Brampton constituency office, and who had taken key positions on his campaign, clashed with the Ottawa party machine. Several former staffers say that in public appearances, they struggled to keep the leader on-script and had to persuade him not to just “wing it."

In a scrum in April, 2018, outside the House of Commons, Mr. Singh was unsure of his own party’s position on a recent gun control bill. In a CTV interview this past January, when asked to respond to comments from the Chinese ambassador amid a continuing trade war, Mr. Singh was unaware of the latest developments.

Granted, he has made up much of that ground in the campaign, gaining confidence with each week. As for his earlier fumbles, Mr. Singh believes the reaction was overblown. “The people I talk to – their lives, what they’re going through – is this something that’s going to change their life?” he asked. “No.”

When pressed on the fact that some Canadians have had their livelihoods threatened by the trade war – canola farmers, for example – he became impatient. “So, it was who said what about who,” he said, the words spilling quickly from his mouth. “I obviously want to be as prepared as possible and always be on top of every issue that comes up. But I don’t see that as a thing that impedes the life of someone that I’m trying to improve.”

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Meanwhile, the party itself has struggled to fill out its ranks. Eleven of its 39 MPs announced they wouldn’t be running again, and by Day 1 of the campaign, it had nominated fewer than 200 candidates for 338 ridings. (It now has a full slate.)

Mr. Singh tried to paint that as a positive – an “exciting” opportunity to bring in new faces. He cited the example of a “rising star” he had recruited to run in Hamilton. “Dave Christopherson is going to continue to help out,” he said, referring to the long-time MP who announced his retirement last year. “He’s actively supporting” – he paused for several seconds. He clasped then unclasped his hands.

Turning to his assistant, he asked: “Do you remember his name?"

The assistant shook his head. Mr. Singh was silent, a bewildered look on his face.

“Oh my God. Let me come back to his name,” he muttered. “Um, let me come back to his name.”

A few moments later, in the middle of another thought, he finally came up with it: Matt Green. His face lit up. “So, we’ve got two people: the brand new city councillor running and the veteran helping him. It’s great.”

A few days after the brownface scandal erupted, Mr. Singh appeared on the French-language talk show Tout le monde en parle, which regularly draws a million viewers an episode – roughly 10 per cent of Quebec’s population.

For Mr. Singh, it was a crucial night. His chances in the general election are directly tied to his performance in Quebec, where there are 78 seats up for grabs. In 2011, Mr. Layton’s Orange Wave took 59 seats (in large part thanks to a successful appearance on Tout le monde en parle), a figure that was reduced to just 14 under Mr. Mulcair. All of those seats are now in jeopardy, with polls putting the NDP in fifth place, behind the Liberals, Bloc Québécois, Conservatives and Greens.

With the show’s upbeat music playing, Mr. Singh bounded onto the stage. Host Guy Lepage wasted no time, aiming his first question squarely at Mr. Singh’s yellow turban: What does he say to Quebeckers who are against politicians wearing religious symbols?

The question was a reference to Quebec’s Bill 21, which ushered in a ban on government workers wearing religious symbols. Bill 21 means that Mr. Singh – who could, in theory, lead the country – could be banned from holding many government jobs in its second largest province.

Outside Quebec, he has described the law as “state-sanctioned discrimination.” Tonight, however, his answer was more nuanced. As Mr. Lepage’s co-hosts nodded politely, Mr. Singh called himself an “ally” to Quebec. He promised to give the province more money for immigration and culture, and to allow for an opt out of federal programs, with compensation. He also said that, although he personally stands against Bill 21, he wouldn’t interfere with a legal challenge.

It was not his first attempt to connect with Quebeckers. Early in the campaign, he created Quebec-specific ads that show him with his hair down, tying on his turban. “Like you, I’m proud of my identity,” he says in the French-language ad. Repeatedly, he has drawn parallels between Quebeckers’ feelings of being a minority with his own experience as an outsider.

But will that be enough to win over a province where many believe multiculturalism poses a threat to its distinct identity and where hate crimes are steadily rising? From 2015 to 2016, Quebec saw a 21-per-cent jump in such crimes, with a large proportion directed at Muslim and Arab communities. In 2017, they jumped another 49 per cent.

It’s not just Quebec. Comments on Mr. Singh’s social media posts are frequently littered with racist language. Some journalists on Parliament Hill continue to mispronounce his name (it’s Jug-meet). During a stop in Toronto, he was mistaken in front of a Globe and Mail reporter for Harjit Sajjan, the Liberal cabinet minister, despite the fact that they look nothing alike, and Mr. Sajjan is nearly a decade older. But they both wear turbans.

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Race has been a factor for Mr. Singh’s campaign from the start. Initially, at least, it was seen as an asset, proof of the NDP’s progressive bona fides. There seems to have been an assumption that, despite the diversity of Canada’s South Asian communities – and the deep and lingering divisions between Sikhs and Hindus – that the Indian diaspora would unite behind him, along with other minorities and historically marginalized communities.

It’s not that simple. Early on, his team showed his image to focus groups and asked for their reaction. “Quite frankly, some people – a lot of people – think he’s a fundamentalist Muslim. They just don’t know,” says Michael Balagus, a senior adviser on the Singh campaign. “They assumed that this must be a very, very socially conservative person, dressed in this religious garb.”

If anything, Mr. Singh’s candidacy has shone a spotlight on how poorly equipped much of the country remains in having nuanced conversations about race. In the hours after the release of the brownface image, reporters on Mr. Trudeau’s plane – a group that did not include a single person of colour – focused almost entirely on what the image would mean for the Liberal campaign. The conversation about race was flattened into questions such as: “Is this photo racist?”

Mr. Singh, meanwhile, has faced repeated questions about his views on Sikh separatism, with journalists asking him to explain his attendance at events where speakers have called for an independent Khalistan.

At one rally in particular, in 2015, Mr. Singh spoke in front of a poster of Jarnail Singh Bhindranwale, the leader of an armed extremist group. In response, Mr. Singh has said his attendance at such events was focused on promoting peace. “I have always tried to give space to all voices so that we can move together towards peace and reconciliation,” he wrote in The Globe last year.

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Others have questioned an exchange that took place between Mr. Singh and former CBC reporter Terry Milewski, who asked him – on the day after he was named NDP Leader – for his views on Talwinder Singh Parmar, identified by the Air India inquiry as the mastermind behind the bombing. Repeatedly throughout the interview, the reporter demanded that Mr. Singh denounce Parmar. The newly minted leader sidestepped the questions, condemning the attack itself, but opting to focus on bridging the divide between Hindu and Sikh communities. For days afterward, Mr. Singh was accused of “refusing” to condemn a terrorist. (In later interviews, he explicitly condemned Parmar.)

To his supporters, the fact that he was being asked these questions only reinforced their belief that Mr. Singh faces a different standard.

Other Canadian politicians, including Justin Trudeau, have also taken part in events, such as the annual Khalsa Day parade in Toronto, where separatist messages are commonly displayed. Besides, they argue that religious violence in India, its effects on Sikh identity and the issue of intergenerational trauma are complicated – not well-suited for the blunt questioning Mr. Singh has faced from mostly non-Sikh journalists.

Sarbjit Kaur, a communications strategist who is Sikh, called such questions “outright inaccurate, unfair, misguided” and, ultimately, “exhausting.” Ms. Kaur, who is a Liberal, says, “I’m not NDP, but I was really, really upset when those types of allegations were being made the day after he did something so historic.”

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For all those who worry that Mr. Singh’s race and religion have become too front and centre in his candidacy, there are others who criticize him for the opposite. During the debate this week, after Mr. Singh said he would not intervene on Bill 21, he was attacked by Mr. Trudeau for putting politics first.

Toronto-based activist Desmond Cole, who worked alongside Mr. Singh in campaigning against police carding of racialized communities, says that Mr. Singh has let down some of those same groups since taking on the NDP leadership.

“I have been disappointed with Jagmeet Singh since he became leader of the federal NDP – deeply disappointed,” says Mr. Cole. He questions whether Mr. Singh has been overly concerned with being labelled radical. “You could argue that being a brown, Sikh man in a turban, being the first person of colour to lead a political party – that a lot is being asked of him in that scenario,” Mr. Cole says. “But what’s the point? What are we celebrating when you’re the first person of colour but when [issues facing racialized persons] come up, you say, ‘It’s too risky for me to say something?'”

Mr. Singh counters that he has, in fact, been taking strong positions, adding simply: “My existence is a strong position.”

He recognizes that all this – having his actions dissected and endlessly parsed for significance – is part of the burden of being the first. He also realizes that his performance will likely determine how much longer it will be before another racialized person is given the same opportunity. “It can inspire more people. Or, if the backlash is so much – if it’s so difficult and so negative – maybe it discourages people,” he says. “I feel that weight, that burden. I’m aware of it, and I’m motivated by it.”

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Spend enough time around Mr. Singh, and you’re bound to hear him utter the words “charhdi kala," a Punjabi term from Sikhism he first learned from his mother that translates roughly into “optimism.” It’s the belief that, in the face of adversity, you must maintain a positive mindset.

It will take a lot more than optimism to propel Mr. Singh to a win on Oct. 21. Even with the small bump in support following the brownface scandal, the NDP have only just managed to pull ahead of the Greens.

Some have also questioned whether Mr. Singh even wants the top job, arguing he conceded the race before it even started, when he said in August that he wouldn’t prop up a Conservative minority. But that’s nothing new, say his supporters. “They always count my brother out,” Gurratan says. “And he’s consistently proven them wrong.” For proof, he points to the 2017 heckling incident in Brampton that first propelled Mr. Singh into the spotlight. He led the crowd in a chant of “love and courage” to drown out the heckler – the motto his team had only just created for him.

“What we were interested in was creating a movement,” says Mo Dhaliwal, the strategist who came up with the slogan. “Because what’s different about this guy is how he conducts himself. Yes, he has interesting policy ideas, but he has a way of being that’s so unique.”

That way of being – the charhdi kala – is what has seen him through his toughest challenges: the bullying, the abuse, his father’s addiction. It also signifies a small but crucial difference in how Mr. Singh approaches the world: He refuses to define himself by his race or by the racist acts he’s been subject to. Instead, he defines himself through his responses to those acts.

“Living in the struggle, living when things are tough, is very normal for me,” he says. “Those painful things taught me to see the connection we share – that we’re all often feeling like we don’t belong, and that many people are also hurting and struggling."

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Sitting in the park in New Westminster, Mr. Singh – the man who either just wants to hang out on the grass or the politician trying to evoke the late Mr. Layton – repeats what he said earlier.

“I’m fighting to become PM," he says. "I’m running to become the prime minister of Canada.”

He used to watch the leader debates as a kid growing up in Windsor, he continues. If you’d asked him then what a prime minister looked like, he would’ve pointed to someone who looked like Mr. Scheer or Mr. Trudeau.

Now, children across Canada have had a chance to see him up on the stage, looking calm and confident – and very different from his opponents. “If you ask them what a PM looks like, they’re going to say, ‘It can look like anything.’”

He smiles at the thought. “That’s an awesome and powerful thing.”

That optimism could be an act of self-delusion, or it just might be an act of courage.

Editor’s note: (Oct. 10, 2019): An earlier version of this article incorrectly referred to Erin Weir as a Saskatoon MP. This version has been corrected.

Editor’s note: (Oct. 11, 2019) An earlier version of this article said NDP leader Jagmeet Singh would be banned from holding a government job in Quebec. Only government employees "in a position of authority" are prohibited from wearing religious symbols under Bill 21.