OTTAWA—Jagmeet Singh was supposed to be in Chicoutimi.

Headlines heralded the arrival of all three major party leaders to the riding north of Québec City last week, just days before a federal byelection. Singh, Prime Minister Justin Trudeau, and Conservative Leader Andrew Scheer were actually expected to appear at the same event: the opening leg of a long-distance bike ride.

When the time came, though, photographs captured a sportsmanlike handshake between Scheer and Trudeau. Singh was nowhere to be seen.

It turns out the leader of Canada’s New Democratic Party missed his flight from Ottawa that morning. So while his opponents yukked it up with the good people of Chicoutimi—Le Fjord, Singh was stuck behind the wheel for a long haul drive from the nation’s capital, only to arrive later in the afternoon.

“He was actually extremely ill that morning, and wasn’t able to get on his flight,” said James Smith, Singh’s press secretary.

“He’d been going hard.”

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Some would say it’s actually the going that’s been hard on Singh.

At the end of a spring parliamentary session dominated by pipeline politics, trade disputes and the disorienting antics of the U.S. president, the federal NDP and its leader-without-a-seat are still searching for a breakthrough. In the final days before Parliament rose for the summer, Singh was on his heels after Monday’s byelection defeat in Chicoutimi—Le Fjord, the seventh in a row where the NDP vote-share dropped compared to the 2015 election — and, this, in a riding the NDP held from 2011 to 2015 and narrowly lost in the last election.

What’s more, the resounding loss — in which the NDP scored a paltry 8.7 per cent in the byelection — provoked concern about the security of the party’s Quebec base, a 16-seat remnant of the 2011 Orange Wave under Jack Layton. That had Singh pledging to place “everything on the table” for potential changes in order to gain traction in the francophone province and set his party in the right direction. The situation was bad enough for Singh to field questions from journalists about whether he will even still be the NDP leader for the 2019 election (he said yes, he will be) and whether his MPs have asked him to resign (no, they haven’t, he said).

A big part of the problem, said long-time NDP strategist and Summa Strategies vice-president Robin MacLachlan, is that nine months into his job as party leader, Singh has to spearhead the caucus from the parliamentary sidelines.

“I think any stumbles that the NDP had (this year)... can probably be rooted in Jagmeet Singh not being able to lead the caucus in the House of Commons,” he said.

“It’s becoming clearer and clearer that not having a seat is holding the NDP back.”

This week’s troubles didn’t spring from nowhere. The past six months have seen Singh attempt to steer his party through a parade of obstacles. There have been rumblings of discontent in his own caucus, which broke into the open in March when prominent MPs publicly questioned his decision to turf veteran New Democrat David Christopherson from his committee chair role after he voted his conscience against party lines. Singh reversed the punishment in the face of the discontent.

Meanwhile, two of his MPs have been accused of sexual misconduct, with one now sitting outside of caucus under the anachronistic banner of the Cooperative Commonwealth Federation (the Prairie-socialist precursor to the NDP), and another awaiting the results of an investigation into an allegation that she took an inappropriate romantic interest in a soldier with post-traumatic stress disorder.

Amidst it all was a week where the NDP leader was under intense scrutiny over videos that emerged showing him at pro-Sikh independence events in recent years. In one film, Singh spoke on a stage with an image of a controversial religious figure killed in the 1984 army massacre at the Golden Temple in Amritsar. The other video showed him next to a Sikh youth leader who said violence can be a “legitimate form of resistance” for Sikhs in India. Forced to wade into the complex history of Sikh oppression and extremism in a foreign country, Singh at first said questions of political violence in the Sikh-Indian context were too complex to be answered "in a simplistic manner." When that did not play well, he changed tack, condemning "absolutely" all forms of political violence and promising not to attend any event where he knows in advance someone will advocate violence as a tool. He also denounced the man widely considered to be the mastermind of the 1985 Air India bombing, something he had refused to do in an interview with CBC shortly after he won the NDP leadership.

All together, it makes for a bumpy road since Singh won the party leadership last fall. But the leader remains outwardly optimistic. On Wednesday afternoon, Singh sat in the sun behind Parliament’s Centre Block, underneath statues of 19th-century leaders from Upper and Lower Canada, Robert Baldwin and Louis Lafontaine.

Asked how he would characterize the way things are going, Singh highlighted NDP positions that he said demonstrated “bold leadership” in key areas that show a clear difference between his party and the ruling Liberals. He praised NDP MP Romeo Saganash, who sponsored a bill that passed through the House of Commons in May, which is aimed at ensuring Canada’s laws are in line with the United Nations Declaration on the Rights of Indigenous Peoples (UNDRIP). Singh called it “one of the most historic and profound legislated changes to our Canadian legal framework.”

He also pointed to the party’s staunch opposition to the Trans Mountain pipeline expansion, which has divided NDP governments in Edmonton and Victoria and prompted criticism from Alberta Premier Rachel Notley, who once called Singh’s position on the pipeline “ridiculously naive.”

Finally, he spoke about Vancouver MP Jenny Kwan, who made the case in Parliament for months that Canada should suspend the Safe Third Country Agreement with the United States, which many argue creates an incentive for thousands of migrants to cross irregularly into Canada.

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Then there was the Ontario election, when polls put NDP Leader Andrea Horwath in contention for power, and the party wound up as the Official Opposition for the first time in more than a generation. Singh, who was an MPP at Queen’s Park from 2011 until he became federal leader last year, spent much of May on the campaign trial for the provincial party, boosting candidates — including his younger brother, Gurratan — who won seats at Queen’s Park in Toronto and the GTA.

“I’m really proud,” Singh said. “It shows that there’s a real appetite for the progressive values that we have as New Democrats in Ontario... It’s really encouraging.”

MacLachlan agreed the Ontario result should put some wind in the sails of the federal party. He also said the policies Singh highlighted — enshrining Indigenous rights in Canadian law, and opposition to the Safe Third Country agreement and Trans Mountain expansion — represent openings for the NDP to woo left-leaning voters away from the Liberals.

“We’re kind of coming to the end of the first phase of Jagmeet Singh’s leadership,” MacLachlan said, adding that Singh’s presence for strong provincial election results in B.C. and Ontario bodes well for the party in the 2019 vote, and could help dispel any lingering doubts about his leadership.

“It’s essential that we regain seats in Toronto,” he said.

For David Coletto, chief executive of Abacus Data, it’s obvious the party has failed to gain ground in recent months, even if it’s not clear what exactly the problem is. While his firm’s data suggests almost half of Canadians are open to voting NDP, many on the progressive side of the spectrum haven’t turned away from Trudeau and the Liberals.

“I don’t think Jagmeet Singh has done anything to earn a hearing from Canadians yet,” he said. “There has to be spark, there has to be some way to pay attention, and I don’t think the NDP have found that opportunity.”

Karl Bélanger, president of the Douglas–Coldwell Foundation who was principal secretary to Thomas Mulcair when he was Opposition Leader for the NDP, said concerns about the direction of the party under Singh are well-founded, especially given the fact that Canada is about 15 months away from the next federal election.

“(Singh) needs to find that magic touch again, the one that he had that allowed him to win the leadership,” Bélanger said. “Time is running out to fix the ship.”

Back beneath the Baldwin-Lafontaine statue, Singh acknowledged there is need for improvement. His immediate plan is focussed on Quebec, where concerns are perhaps greatest that the bottom is falling out. He will spend more time in the province, and is open to tinkering with his messaging and looking to hire staff from Quebec in an effort to connect, he said. Asked for more specifics, Singh said figuring that out is part of what needs to be done.

“I’m never afraid of a challenge. I’m always up for it. And this is just another challenge that I’m prepared to take on,” he said.

As for the eventual necessity of winning a seat, Singh repeated his line that he’ll take advice on when and where to run — potentially in Burnaby-South when incumbent Kennedy Stewart leaves to run for Vancouver mayor. But he said he’d still be confident going into the 2019 vote without a seat, as he and his party work on finding a way to gain momentum in the coming months.

“I think some of it is — it just takes time,” he said. “It takes time to bring in the changes you want to bring.”

A little more than one year out from election season, time is getting shorter for Singh and the NDP.

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