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In his second federal race, the NDP Leader and his team are bringing a more seasoned strategy and renewed confidence

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NDP Leader Jagmeet Singh waves goodbye as he gets back on the bus outside his campaign office in Burnaby, B.C. He and the New Democrats are aiming to increase their seat count in the Sept. 20 vote.Darryl Dyck/The Globe and Mail

In person, Jagmeet Singh is magnetic, charismatic, joyful. The 42-year-old’s personal popularity – he is the best liked party leader, by some distance according to a recent Ipsos poll – is even stronger than his TikTok game. But in this second election as NDP leader, he is no longer just an ebullient upstart.

One major difference between this and the last, those close to him say, is the nuance and complexity he brings to debates over policy.

The problem with nuance, in politics at least, is that leaders who espouse it risk being misunderstood – seen not as smart, but spineless, fuzzy, vague. (So, the once-vocal opponent of the Trans Mountain expansion now refuses to say whether as prime minister he would cancel the controversial pipeline project.) This isn’t to say Mr. Singh’s approach hasn’t moved his party forward.

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Mr. Singh takes part in an election-night party in Burnaby, B.C., on Oct. 21, 2019.Darryl Dyck/The Canadian Press

The Windsor-raised, second-generation Sikh lawyer didn’t exactly win big in 2019. But he retained his seat in Burnaby and did better than many pundits – and high-ranking New Democrats – thought he would. He did it largely by offering unbounded optimism to a party that for a half decade had seemed mostly seemed demoralized, downcast.

There were good reasons for the mood. An ugly divorce from leader Tom Mulcair left the party in shambles. Fundraising evaporated as caucus spent the next term practically insensate. Candidate recruitment collapsed. In the weeks leading up to the 2019 campaign – Mr. Singh’s first outing as leader – the NDP was polling in fourth and sometimes fifth place, staring down the possibility of a bloodbath. The leader began the campaign on a bus, because his party couldn’t afford a plane.

Initially, at least, Mr. Singh seemed to offer little in the way of help. He was often caught flat-footed, and seemed to struggle to retain the support of his caucus. When 11 NDP MPs chose not to run in 2019, it looked like they were abandoning ship.

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Mr. Singh and Liberal Leader Justin Trudeau shake hands after one of 2019's leaders' debates.Adrian Wyld/Pool via REUTERS

Then came his moving response to the prime minister’s blackface revelations in the first week of the 2019 campaign. He followed up with a stellar rookie outing in the English-language debate. More memorable still was his deft handling of a bigoted Montrealer who recommended he “cut off” his turban just hours before the French-language debate. (“I think Canadians look like all kinds of people,” he replied. “That’s the beauty of Canada.”)

No, it didn’t herald Singh-mania. But it was enough to pull the party back from the brink of collapse. Behind the scenes, NDP insiders say, Mr. Singh was resolute when his leadership was questioned. He buckled down, got better at his job, and let Canadians get to know him and understand what he was all about.

But as he attempts to grow support for the NDP, he is facing new and unexpected competition as Conservatives try to siphon off the labour vote in this campaign. Mr. Singh, in devoting so much time and energy to shoring up his support on the left, has left himself open to this fox-in-the-henhouse raid from the right.

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At a Sept. 15 stop in Welland, Ont., a sign bearing former NDP leader Jack Layton's name is held alongside those supporting Mr. Singh and this year's New Democrat candidates. This past August was the 10th anniversary of Mr. Layton's death from cancer, which began a period of soul-searching in the party that brought Tom Mulcair, and then Mr. Singh, into the leadership.Nick Iwanyshyn/Reuters

Healing rifts within the caucus was the first order of business coming out of the 2019 election. “People who come to Ottawa from provincial politics often think, I got this – piece of cake,” says Libby Davies, a former MP for Vancouver East who served as deputy leader to both Jack Layton and Tom Mulcair. “The reality is, Ottawa can be brutal. Jack had buns thrown at him when he first got there from Toronto. The Press Gallery laughed at him.”

Like Mr. Layton before him, Ms. Davies says, Mr. Singh, a former Ontario MPP, set out to build relationships with his caucus, meeting his MPs for coffee, learning what was going on in their lives and who they were as human beings. He spent time with several in their ridings – in Nunvaut, Vancouver Island and northern Ontario – at least until he was grounded by the pandemic. Nobody comes into a federal party knowing how to do the leaders’ debates, the scrums, the national interviews, says adviser Marie Della Mattia. “But Jagmeet has been willing to listen and take advice and when necessary, change course.”

Next was overhauling the personnel surrounding Mr. Singh. The team he imported to Ottawa had little experience with the federal scene. Some were yes men who let his worst ideas go unchallenged, like trying to wing it in front of national media. This time around, the party has bulked up its campaign staff to 100. They brought in NDP stalwarts like Anne McGrath, a confidante of Mr. Layton’s, who also worked for Mr. Mulcair and Rachel Notley, the leader of Alberta’s NDP. Ms. McGrath’s presence alone inspires confidence, says Marcella Munro, Ms. Notley’s communications director. “I remember when Anne first joined the premier’s office in Alberta. It was like: Okay, mom’s home.”

Directing campaign strategy from Ottawa is Jennifer Howard, a former finance minister from Manitoba and Mr. Singh’s chief of staff. Ms. Della Mattia, another party loyalist and former adviser to B.C. Premier John Horgan, is providing advice on tour. Rounding out the all-female team is Laura Ziemba, the “wagonmaster,” responsible for getting Mr. Singh where he needs to be.

Fundraising has also expanded under Mr. Singh. This has allowed the NDP to target ground-game resources and leader’s visits at a specific list of ridings they hope to pick up – Sudbury, Regina Lewvan, Edmonton Griesbach, Port Moody-Coquitlam, Berthier-Maskinongé, among them. They’ve made slick campaign videos for new candidates like Melissa Chung-Mowat, a Métis-Chinese candidate with North End roots whom they hope might pick off Winnipeg North from the Liberals.

It’s also let them deploy sharper, punchier ads. (Those running in Quebec right now show Mr. Singh dumping champagne on a monocled billionaire in a bathtub.) Internal research shows that the more viewers see him, the more they like him.

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Mr. Singh looks at the camera at an Instagram Live session in Vancouver.Jonathan Hayward/The Canadian Press

But the biggest change has arguably been in Mr. Singh himself. People around him say he is better able to stay on script. He’s gained confidence and a firmer grasp of the issues.

Ms. Munro, who says she hasn’t decided whether to vote Liberal or NDP in this election, notes that whereas Mr. Trudeau tends to stiffen or appear overrehearsed when the situation grows tense or beyond his control, Mr. Singh is able to centre himself and be graceful.

Moe Sihota, a former MLA in B.C. and the first Indo-Canadian elected to a provincial legislature thinks that in a “changing Canada,” one of Mr. Singh’s biggest strength is his ethnicity – though it brings its own set of challenges, the NDP strategist admits. “You overcome any hesitation people may have through competence, communication, and sincerity. At some point, people start seeing you as the person you are.”

And the more Canadians see of Mr. Singh’s playful, hopeful persona – and the hoser accent, the skinny suits, and the Crayola-hued turbans – the more they seem to like it. When pollsters ask which leader best understands ordinary Canadians, he outpolls Mr. Trudeau three to one.

This type of methodical strategy of building the party behind a leader brick by brick has worked for the NDP before. The party rose steadily from 13 seats in the 2000 election to 19 in 2004, to 29 in 2006, then 37 in 2008. They did it under a single leader, Jack Layton, who went on to become the most successful leader in the party’s history, taking 103 seats in 2011.

That breakthrough, the Orange Wave, as it’s known, is often depicted as a fluke. But party insiders insist it was the careful result of a decade’s work. Mr. Layton did it by first winning over his party, then his caucus, and eventuall,y hundreds of thousands of new voters, mostly through the sheer force of his joyful, hopeful personality. Sound familiar?

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Mr. Singh and Gurkiran Kaur Sidhu wait on their campaign bus to be introduced to a crowd at a Sept. 15 stop in Brampton, Ont. The couple are expecting their first child.Jonathan Hayward/The Canadian Press

Mr. Singh’s story is also evolving. His wife, Gurkiran Kaur Sidhu, is pregnant with the couple’s first child. Mr. Singh, who speaks in dulcet, surfer tones, says he is “soo stoked” to become a dad. Talk of his impending fatherhood got the supremely laid-back New Democrat Leader more animated than anything else on a cold and rainy whistle stop in Coquitlam last week.

He had arrived decked out in an all-Canadian outfit – white golf shirt by Reigning Champ of Vancouver, dark jeans by Naked and Famous of Montreal, pale brown cardigan by Outclass of Toronto and a neon pink turban he picked up in Mississauga. Buzzfeed anointed him, with reason, the “most stylish politician in Canada by like a million kilometres.”

The flashy style belies a profound insecurity.

Mr. Singh started sporting the pinstripes and bespoke shirts when he first began appearing in Toronto area courtrooms as a young lawyer, he says. He felt out of place. The feeling was not new to him.

At school in Windsor, Mr. Singh says he was laughed at, beaten, and called “diaper head” and “Paki.” Kids would yank and twist his long hair.

That was just one part of his pain. When he was 12, he was sexually abused by his taekwondo coach. The man’s approach was deeply manipulative – “really nasty, really psychological, really gross,” says Mr. Singh. The experience, which he kept secret for more than a decade, left him feeling “dirty” and like he “didn’t deserve love.”

At roughly the same time, his father’s alcoholism was spiralling out of control. His dad would go on to lose his medical licence and the family home, and had to file for bankruptcy.

Mr. Singh credits those dark days as the source of the happy optimism for which he has become known: “My hardest day, my most difficult day as an adult is nothing compared to my easiest day as a kid. We would always be wondering if we could make the bills. Or if we’re going to lose our house – all this unpredictability, volatility, scary stuff. I just feel like I’m so lucky to be where I am.”

Years of struggle have also conferred hard-won strengths that have helped him on the national stage, notably his handling of the ongoing national tragedy of the discovery of children’s remains on the grounds of residential schools.

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Mr. Singh pauses at an Aug. 31 stop in Coquitlam, B.C. The Lower Mainland and Vancouver Island are historically reliable NDP bases, but the party lost seats there in 2019 and is hoping to gain ground again.Darryl Dyck/The Globe and Mail

A global pandemic, like a depression or a world war, feels like one of those moments in the clock spins of history when voters turn to social democrats for bold and sweeping solutions. Many of Mr. Singh’s biggest plans – his national pharmacare and child care programs and a wealth tax – have mainstream support.

Meanwhile, he promises to bring the “political will” to end boil-water advisories on First Nations. That same “will” would allow him to achieve his goals on housing. And he has the “will” needed to finally tackle the opioid crisis.

When it comes to providing specifics of how he would do any of these things, or even a compelling reason why he is the person best suited to lead the country, Mr. Singh tends to stick to the same script: Attack Mr. Trudeau for worsening the housing and climate crises, and for letting “the super rich get a free ride.”

The New Democrats, he says, would make “billionaires pay their fair share – so the pressure burden isn’t on the people.”

The problem is, free transit, forgiving student debt, providing national daycare, pharmacare and dental programs, plus all the other NDP promises add up to $241-billion in new spending, the party says. At last count there were all of 41 billionaires in Canada.

Voters, it should be noted, were only provided these costing figures on Sept. 11 – after many had already cast a ballot. The quiet drop landed like a feather on the 20th anniversary of 9/11, a day blanketed by anniversary coverage of the terrorist attacks on the U.S. A cynic might argue that was the point.

Another big problem for Mr. Singh is that all parties are feeling spendy at the moment. Even the Conservatives have offered one of the most activist platforms in decades. It wasn’t that long ago that the NDP stronghold of Vancouver Island was almost entirely swept by the Reform Party, Mr. Sihota notes. He believes Mr. Singh biggest problem is his relentless focus on social issues at the expense of economic matters, a big turn off to some labour voters.

The Conservatives clearly smell blood. Erin O’Toole has made significant outreach to working class voters throughout the campaign with a platform aimed at helping gig workers, giving workers a voice in corporate governance, and speeches lamenting the drop in union membership.

Mr. Singh, however, has largely remained laser focused on Mr. Trudeau, labelling him as “all talk, no action” – also the theme of his most recent ad blitz. Still, at the end of the English language leaders’ debate, he pointed to the Liberal and Conservative leaders and told viewers: “You’re not stuck with these two.” Next week will show whether voters’ believed him.

Editor’s note: An earlier version of this article included an incorrect estimate of the cost of NDP promises. This version has been corrected.

The Decibel: Jagmeet Singh on the issues

Jagmeet Singh of the NDP was the only one of the three most prominent party leaders to accept an invitation to The Globe and Mail’s news podcast. Here’s what he had to say to host Tamara Khandaker. Subscribe for more episodes on the election.

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