A small herd of reporters, NDP campaign organizers, and parents with children recruited to gambol here for the occasion are gathered in a concrete courtyard in downtown Ottawa on a bright fall morning.

The space sits atop a parking garage surrounded by modest rental townhouses, the setting like something from the Sesame Street backlot, with a small play structure and handful of toys in one corner and barbecues and potted plants scattered around the perimeter. Off to one side, a conspicuously inconspicuous RCMP officer wearing a dark suit and a plastic earpiece has installed himself like an Easter Island monolith.

Two campaign organizers chat about the importance of citing real people in policy announcements: “Jack was always great that way. He always had a story of someone he’d met,” the man says. “Sometimes it was like, ‘You sure?’” They talk about the wildcard aspect of putting microphones in front of ordinary people. “You can’t control the narrative,” the woman comments. “Nope,” her colleague agrees.

And then NDP Leader Jagmeet Singh arrives, mounting the courtyard stairs wearing a puffy navy jacket and artfully beaten-up black suede ankle boots, trailed by more Easter Islanders. He dotes on the kids for a few minutes, then strolls over to a microphone. “They’ll give us the thumbs-up,” he murmurs to the candidates at his side, nodding toward the cameras and reporters.

The purpose of this gathering is to announce his party’s affordable housing platform. “We hear Mr. Trudeau talk about that there is a housing crisis—more of those pretty words acknowledging the problem—but then when it comes to the actual solving of the problem, empty promises,” Singh says. “Things are doing better in terms of the economy, but they’re not getting better for everybody.”

A New Democratic government would build 500,000 units of affordable housing in the next decade, he announces, half of them in five years, kick-started with $5 billion in federal funds. He gets several versions of the same question: How will you pay for this? “It’s really a matter of choices,” he says, and argues Trudeau didn’t explain how he was going to pay for a $14-billion corporate tax cut, or the $4.5 billion he forked out to buy the Trans Mountain pipeline. “We will make different choices, we will make housing a priority.”

Singh hits each mark his party would hew tightly to through a remarkably consistent early campaign. The Liberals and Conservatives were both in it for their rich friends and big companies, but never for ordinary people, the NDP leader would contend over and over (while strenuously avoiding any mention of the Greens, who are nipping at his heels in popular support). There was plenty of money to be had for program spending if they quit with the corporate honeypots and closed tax loopholes for the wealthy, the argument went.

Soon, though, the ugliest sort of sideshow would consume the political landscape, with revelations that Prime Minister Justin Trudeau had repeatedly donned blackface in the past. And Singh would be swept up by that narrative in ways that were distinct from the other party leaders. It would compel him to answer endless questions that hinged on other people’s toxic reactions to people of colour, but the way he handled the moment would also cast his supposedly hopeless campaign in a fresh light.

He and his party entered the campaign basically written off: the shine was off the Liberals, and with the climate crisis elevated to oh-my-God, the Green Party seemed poised to eat the NDP’s progressive lunch; seat projections showed them winning as few as five seats. Many of those low expectations were well-earned and supported by objective fact: weak fundraising, veteran MPs not running, caucus tensions and missteps and waffling from the leader. But some of the narrative seemed to be a snake eating its own tail with a delicious side of confirmation bias.

A lot of things happened that made Marie Della Mattia, campaign co-chair and political director, think, “Really? Are we that bad?” when she saw the reaction.

“I was in the green room when [then-premier of B.C.] Christy Clark reached across to put her hand on [B.C. NDP leader] John Horgan’s arm, and he turned to her and said, ‘Please don’t touch me’ in the middle of a debate,” says Della Mattia, who worked as a special adviser to Horgan. “And he didn’t die. The whole thing didn’t come crashing down, it wasn’t a disaster. Everybody didn’t think he was a big idiot and failure.”

Asked why that is, she offers a mirthless laugh. “Well, he’s an old white guy,” she says. “People are hard on people who don’t fit the mould.”

But once the campaign started, the NDP became a low-key Cinderella story. Singh tidily made his case and introduced himself to voters in the first leaders debate, hosted by Maclean’s and Citytv; his campaign was tightly focused on addressing the affordability of everyday life; and his was the only one of the five national parties not repeatedly hauled off message by candidate controversies.

In Ottawa, with the housing announcement complete, Singh and his campaign team head for the NDP bus, bound for northern Ontario and the International Plowing Match, where politicians annually flock to the massive rural crowds.

Wrapped in slick campaign images from the outside, the interior of the bus is pluckily on-brand for a grassroots party going to bat for the little guy. Snacks for staff run to the healthy, family road-trip variety— crackers, rice cakes and trail mix from Costco—while catered lunches are picked up along the way to feed the media (who pay heftily to cover their own costs on tours). When he’s not doing phone interviews or conferring with staff, Singh will catch up on sleep leaning against a window in the last row of the bus, wearing an eye mask. At one point on the road to Verner, Ont.—a small town between North Bay and Sudbury—he sidled up and down the aisle with an elastic exercise band around his knees; later, he stood next to the washroom wearing a “Downtown Oshawa” T-shirt and steaming his chambray button-down while Wheat Kings played on the bus’s sound system.

At the plowing match, Singh emerges from his bus into a crowd of NDP supporters. “I see you on TV all the time,” a 60-ish man in a plaid shirt and brown snapback hat beams. “You look just like that.” By “that,” his tone suggests he is delighted to find that real-life Singh looks just like as-seen-on-TV Singh.

This event is so popular as a glad-handing opportunity that the Ontario legislature takes a day off when it is in session so everyone can attend. When it’s Singh’s turn on the tractor, in spite of his lawyer-in-bespoke-suits-on-a-bike-in-midtown mien, he does not look awkward astride the mechanical beast. The orange-clad crowd hoots and applauds as he carefully steers while peering down at the path he’s carving into the earth, then he and the bus entourage ride an open wagon toward a sprawling tent city of food and merchandise vendors.

They stop in front of a food truck where the woman inside recognizes Singh, and he demonstrates that weird politician’s talent for saying “Good to see you!” to a complete stranger so that it sounds like he’s been waiting all day for that specific person to show up. The woman passes Singh a big basket of fries and he tries several times to pay for them, but she refuses.

A small crowd of onlookers hovers nearby, grinning vaguely with what may be recognition of who Singh is or just the knowledge that he’s someone, and now he’s here. A staff member and a couple of reporters stand off to the side, discussing a farmer who spoke to Singh genially, but admitted she won’t vote for him because she doesn’t think the country is ready for “someone like him.”

This will come up again and again, even before the blackface story consumes all the oxygen. Some of the people who make these comments—freely, as long as the cameras are not rolling—say they personally are just not ready to vote for him, while others magnanimously assign the hesitancy to the country at large. Singh’s staffer comments that every event like the plowing match gives voters another chance to see that Singh isn’t “someone like him,” but rather someone like them.

The group herds back onto the wagon. Singh is mostly vegan but easily wooed by cheese curds, and he passes around a bag of dill pickle-flavoured ones with the fervour of a new recruit to a multi-level marketing scheme. Then it’s back to the bus for the next leg of the tour.

A few days earlier, Singh did an interview and impromptu tutorial video with a journalist aboard his bus. It was the sort of charming and humanizing “earned media” strategists generally drool over; he demonstrated how he can wind his hair into a tight bun without using any accessories to secure it, then explained some of the purpose and symbolism of the turban. “I always loved when people came up to me and asked me questions,” he said. “Ask away. It’s better that people ask.”

But still, every minute of air time or inch of print he spends answering questions about his Sikh faith or garb is a moment he’s not talking about policy or what his party wants voters to know. And all the public appearances in which a few voters at a time come to understand that he’s just like them—or don’t—is time spent filling in a pit someone else dug for him.

Singh is resolutely sanguine and philosophical in the way he discusses all of this—in an interview, he uses the word “frustrating,” but then immediately walks it back—but he acknowledges briefly that sometimes people’s focus on the way he looks interrupts his ability to talk about the issues he cares about.

When he was an Ontario MPP, a female colleague chortled: “Yeah, welcome to the life of women, it happens all the time.” So Singh’s view now is that he may get judged for the way he looks, but plenty of others experience the same because of their gender, faith, race, sexuality or untold other aspects of who they are, and his experience attunes him to theirs and spurs him to speak for all of them. “Every time I’m asked, I’m pointing out that this is a problem that’s bigger than just me,” he says.

And in a broader way, this underdog-defender role maps perfectly onto the NDP political promise. Singh’s rebuttal to other people’s hang-ups about race or religion is to simply do his thing and wait for them to figure it out. “It’s going to be at the end of the day, ‘Uh, I don’t like his beard and turban, but he wants to take on the wealthiest and make my life better, and bring in denticare and pharmacare and build housing and do all the things that are gonna make my life and my kids’ life better. How can I not like those ideas?’” he says.

Jennifer Howard, NDP campaign manager, knows all the extraneous questions are just the way life is, but she sometimes wishes he could simply talk policy. “But I also live in the real world,” she says. “And I know that Jagmeet is not just the leader of the NDP; he is also the first racialized person to lead a national party in this country, and that does come with additional responsibility. And he has, I think, beautifully risen to that responsibility.”

Singh will get a chance—at first—to focus on policy that evening at a town hall on affordability at the United Steelworkers Hall in Sudbury. Inside, a wall-sized Canadian flag plays backdrop, and, adhering to the rules of political staging, the room is too small by 20 per cent for the crowd, lending things an intimate, packed-in atmosphere that on TV will look monumental.

Singh arrives to big cheers and a standing ovation from about 200 people, then gives a short speech, emphasizing that the Liberals and Conservatives are just red and blue versions of the same thing, in it for the rich and not the regulars. “The economy is booming, but who is it booming for?” Singh asks. The Greens, as usual, are Voldemort: They Who Cannot be Named.

Virtually all the questions from the audience lie outside federal jurisdiction: services for children with autism, health care and medication, disability benefits and workers’ compensation among them. As a result, most of Singh’s answers are long on empathy and validation and short on details, but the crowd seems to find this entirely satisfactory.

At one point, he talks about how tuition shaped his path in life. His family struggled financially when he was growing up in Windsor, Ont., when his father was deep in the throes of alcohol addiction. “I went through a hard time and my way out was law school, which cost $8,000 a year then,” Singh says. He asks the crowd to guess how much that tuition is now, and someone immediately shouts out $40,000. “You just jumped right to the . . . could you let me build up my story?” he sputters in mock exasperation, drawing a big laugh, before supplying the answer he was trying to build into a narrative flourish: the tuition that rescued his life is now $30,000 a year. “I can tell you with all honesty, I would have never done it,” he says. “We want to work towards a country where from kindergarten to your career, there’s no barriers, kids can pursue any dream.” The line draws reliable cheers, as do many others, but there isn’t yet much populist firebrand energy in Singh’s campaign to match the message.

The evening ends with questions from the media. The first reporter says she spoke to a few voters in Verner who said they like Singh and his party, but they’re not ready to vote for a prime minister in a turban. How frustrating is it to hear that, she asks, and what would you say to them? “I believe in Canada, I believe in Canadians,” Singh says. “I believe Canadians are ready for someone who’s going to put them first. We’ve seen Liberals and Conservatives continue to take people for granted… I’m not going to take Canadians for granted.” Another reporter poses a more pointed question: Do you consider these sentiments racist? “I think there’s some prejudice that exists in society. I’ve been told a lot in my life that because of the way I look, I can’t advance in my career,” he says. “I want to build a Canada where no one’s left behind.”

The following evening, Singh was in the middle of another town hall in Toronto when the Time magazine story broke with the first photo of Trudeau wearing extravagantly applied brownface at a 2001 fundraising gala for the Vancouver private school where he was teaching. The journalists in the room immediately saw the alerts, and the phones of NDP staff members began blowing up as they struggled to make sense of what they were seeing.

Campaign staff debated what to do, knowing Singh was about to take questions from reporters: Should they let him process the news in real time, or find a way to give him a heads-up so he wouldn’t be blindsided? “I don’t think anybody has any guidebook for this,” says Howard. “This is unprecedented.” Ultimately, they decided not to intervene.

As the first reporter spoke, Singh took in a slow, silent breath, nodding slightly as she laid out the details of the offensive image, before asking what he thought of it all. Singh nodded a few more times to himself and pursed his lips. “Well, it’s troubling. I mean, really, it’s insulting,” he said. “It’s making a mockery of someone for what they live and what their lived experiences are. I think he’s gotta answer the question why he did that, and what does that say about what he thinks about people who, because of who they are, because of the colour of their skin, face challenges, barriers and obstacles in their life. Racism is real. People in this room have felt it. I’ve heard the stories. I’ve experienced it in my life. He’s gotta answer those questions.” The diverse crowd around him burst into applause.

Afterward, Singh and his team wondered whether they should let those comments stand, or if he needed to say more. “The thing about being the first racialized person to be a national leader is that you have an added expectation to be a leader on issues of race,” says Howard. “There were messages coming in with people really looking for him to say more.”

And so an hour after Trudeau spoke on his campaign plane, Singh stepped before the cameras in a hotel meeting room scrambled for the occasion. He ignored the perpetrator entirely and spoke only to the people who had been hurt by the photo that he said had “jarred” him. “The kids that see this image, the people that see this image, are going to think of all the times that they were made fun of, that they were hurt, that they were hit, that they were insulted, that they were made to feel less because of who they are,” he said, looking directly into the camera. “I want you to know that you have value, you have worth and you are loved. And I don’t want you to give up on Canada, and please don’t give up on yourselves.”

His demeanor cracked when he talked about how he’d been spurred to make a public statement after a friend reminded him that not everyone could battle racists with their fists, as Singh had when he was young. “There are a lot of people that couldn’t do that. They couldn’t fight back. They didn’t have the ability to do that,” Singh said, then paused, looked at the ground in front of him and knocked his knuckles against each other while he composed himself. Finally he finished, with a shrug that suggested he didn’t know where to head next. “They couldn’t. They couldn’t do it themselves. And I think it’s gonna hurt to see this.”

It would swiftly become clear that there wasn’t just one occasion on which Trudeau had worn blackface, but several, and the story gobbled up the campaign for days. Each time he was asked about it, Singh occupied a very specific leadership role, speaking to the people hurting from this and ignoring the motivations, explanations or mea culpas of the man who had seen fit to play dress-up in such a way.

Two days after the story broke, Singh was back in his hometown of Windsor, holding yet another a town hall. At the end of it, a reporter pointed out a supporter in the background hoisting a bright orange sign that paraphrased Singh’s words: “I have value. I have worth. I am loved. Thank you Singh.” The leader hadn’t noticed the sign before that moment, and he wheeled around, delighted. “That sign is what we’re all about. I want everyone to know that you have value, that you have worth, that you are loved,” he said.

Then he paused for a moment and smirked. “And I guess I am Singh, yes,” he said, hoisting his shoulders in a “Here I am” shrug as the crowd laughed and cheered. “That is true.”

This article appears in print in the November 2019 issue of Maclean’s magazine with the headline, “Jagmeet Singh’s moment.” Subscribe to the monthly print magazine here.

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