https://www.thestar.com/politics/federal/2022/10/01/jagmeet-singh-has-matured-into-his-role-as-the-ndps-leader-but-will-that-be-enough-to-make-it-a-contender.html

OTTAWA—Jagmeet Singh is posing for a selfie. Again.

During a late afternoon walk along the Ottawa River behind Parliament Hill, the NDP leader is approached by an exuberant passerby itching to snap a shot. Singh throws up a peace sign as the shimmering lining of one of his customary three-piece suits flashes bright blue in the wind.

The woman tells Singh she is Filipino. “Salamat po,” he replies instantly, thanking her for saying hello. Filipino is one of about 40 languages, he explains, in which he can greet people and ask how they’re doing.

It’s five years to the week since Singh won the NDP leadership on the first ballot, thrusting the not-yet-MP some claimed was too flashy into a political world that this year saw him strike a major governing agreement with the minority Liberals. Now the question is whether that move will help or hinder him when he next hits the campaign trail — a time when Singh will have no choice but to deliver a higher seat share.

For now, he still gets approached wherever he goes. People gawk or follow a few paces behind him, working up the courage to ask for a photo.

That Singh is so well-known, despite the NDP holding fourth-party status, is in many ways tied to what made his 2017 victory so significant.

He was the first racialized person to become the permanent leader of a major federal party, for one.

But Singh wants people to know that his identity extends far beyond that.

“There are a lot of other life experiences that I feel like I draw from more than that,” he told the Star.

His parents filed for bankruptcy and lost their home. He took in his younger brother, former Brampton East MPP Gurratan Singh, while his father grappled with an alcohol addiction. He worked multiple retail jobs. He worried about finding a safe place for his dad to recover.

These threads of Singh’s identity are hardly new revelations for anyone who has followed him as leader of the New Democrats. Today, they form the battle lines he has drawn to present an alternative to Conservative Leader Pierre Poilievre, who has positioned himself as the only viable option for the working class. And they wound their way into the pact he struck with the Liberal government in March of this year.

The Liberal-NDP supply and confidence agreement, the largest accomplishment of Singh’s leadership thus far, was a calculated risk. In exchange for backing the Liberals, the governing party would agree to move on a number of NDP priorities in the hopes of staving off an election until 2025.

“I intuitively knew that forcing the government to do things would make some people frustrated. Some people would be angry about that,” Singh said, of criticisms that he is a traitor, a sellout, a Liberal prop.

But party insiders say Singh’s ability to go head to head with Prime Minister Justin Trudeau in the final weeks of arranging the deal were a sign he was ready to take the leap.

“He had very good arguments, and he was also able to acknowledge when counterpoints would be made that should be considered,” recalled NDP national director Anne McGrath.

“It really was Jagmeet and the prime minister talking about many of these issues, sometimes disagreeing, sometimes pushing harder, and then at the end of the day, coming to something that we thought we could accomplish together,” said Jennifer Howard, Singh’s chief of staff.

For Singh, the deal was always about proving the NDP could actually deliver on some of its long-sought demands, like national dental care and pharmacare programs.

He is partially on his way: dental care for low-income youth is among a trio of affordability measures the Liberals introduced in September in an effort to meet the NDP’s end-of-year deadline.

Singh now has his sights trained on the end of 2023, when more NDP demands must be met to keep the deal alive. Among them is expanding the dental care program, passing legislation that would pave the way for national pharmacare and introducing legislation that would ban the use of replacement workers when employers of unionized workers in federally regulated industries lock out employees.

Both party insiders and observers say the Singh who hammered out this agreement has come a long way from the Singh who bounded off a triumphant leadership run and straight into a disenchanted party.

Indeed, Singh’s first ballot victory surprised even him.

“I am an optimist, but for some reason I was just still unsure,” Singh said, reflecting on the day the leadership race results were announced in a Toronto hotel.

He knew he would win in some fashion — his team said he had brought on board more than 47,000 new party members — but he didn’t know how much of the party’s existing membership would throw down their support. He wound up securing 53.8 per cent of eligible ballots, outpacing his three rivals, including two members of Parliament — Charlie Angus and Niki Ashton — who still sit in his caucus.

One former NDP strategist, who was not a member of Singh’s leadership team, recalled that even though some involved in the race characterized Singh as “all flash, no substance” and lacking the “depth” required to be leader, he was still “the right candidate in the right moment.”

“It was the narrative that everybody wanted,” said the source, who spoke to the Star on the condition they not be named. Singh would be the party’s first permanent leader who was not white. At 38, he was younger than Trudeau, and loved social media.

But he had a shaky start.

The NDP was still finding its way after the death of former leader Jack Layton, who had shepherded the party to Official Opposition status with its remarkable “orange wave” in the 2011 election campaign. The party dropped to a third-place finish in the 2015 election, and the following year, an unprecedented number of party delegates voted in favour of turfing then-leader Thomas Mulcair and naming a new leader.

“Jagmeet was coming into that. He also came into the party when a lot of the fundraising had kind of dried up. A lot of the infrastructure of the party had been left to wither, so he really had to build back from the ground up,” said Howard.

“There’d been massive staff turnover … When I first met him, I expected this guy who’s not that happy, but even then he was optimistic. He understood the challenges in front of him,” she added.

That wasn’t all. Singh grappled with troubles in his caucus. He made missteps in the media.

NDP MP Matthew Green, who backed Singh’s campaign in 2017, noted he didn’t have the institutional knowledge of the House of Commons that most leaders already possess. He was an Ontario MPP and had no seat in Parliament until he won a Burnaby South byelection in 2019.

Five years later, McGrath said Singh is “definitely more polished,” and knows where he should be focusing his time, instead of tackling every issue that comes his way.

“He’s very steady on his feet. He is very good at dealing with unexpected attacks,” he said. “He’s developed a real natural and easy persona.”

Singh is a little more frank.

His French is a lot better, he says, and it’s been a “labour of love” to improve it.

For some, the next test of Singh’s leadership will be the next election.

The NDP lost 20 seats in the 2019 contest, a disappointing result that some blame at least partly on its rough financial situation. In the 2021 election — which New Democrats billed as a pandemic election most Canadians didn’t want — the party gained just one seat in the House of Commons.

“If in the next election he doesn’t increase the number of seats, it’s a failure — it’s a failure of his reign,” the former strategist told the Star.

The next election campaign also must see the party return to grassroots organizing, Green said.

The Hamilton Centre MP said Singh will need to balance “the demands of being caught in the Ottawa bubble versus going out between elections and being relevant” in places where the party has little to no presence.

That point is also made by Abacus Data CEO David Coletto, who says Singh’s public approval ratings get a boost during election campaigns because he suddenly becomes more relevant to Canadians.

Even so, Coletto said, Singh remains “one of the most, if not the most, popular federal leaders in the country.”

While that lead to a “consistent but not rapid rise” in negative perceptions of Singh in the wake of the Liberal-NDP pact, Coletto said the reasoning behind that is more complex.

“What I think’s happened since the Liberal-NDP confidence and supply arrangement is first, a lot of Conservatives have come to view him negatively because he’s, in their mind, propping up the Liberals,” said Coletto, who has seen no evidence that Singh has lost support among NDP supporters.

For Robin MacLachlan, a former NDP staffer and now president of Summa Strategies, the biggest challenge Singh will have to face now is determining whether the Liberals are truly living up to their end of the deal.

“I think (the NDP) are doing the right things now, but they’re going to run up against those decisions repeatedly, and the longer this Parliament goes, the harder that decision will (be) … I would be surprised if it runs up all the way through to the next election,” MacLachlan said.

If the deal runs its course, MacLachlan said, then the NDP will have to defend its decision to back the Liberal government.

“Then you wear all of its warts,” he said. “You wear all of its letdowns.”

Whether the next campaign begins when the deal comes to its natural conclusion or because Singh himself triggers it before then, he says he is ready to take it all on.

As for how long he’ll remain leader, he says his first five years are just the beginning.

“When the point in time comes where I can’t make the same contribution anymore, and I can’t help people and fight for them in the same way, then I’ll consider,” Singh said.

“But I’ve got a lot left in me.”

Raisa Patel is an Ottawa-based reporter covering federal politics for the Star. Follow her on Twitter: @R_SPatel