Open this photo in gallery NDP Leader Jagmeet Singh makes an announcement in Toronto on Monday, Sept. 2, 2019. Christopher Katsarov/The Canadian Press

Jagmeet Singh won’t be touring the country during this fall’s election campaign the way leaders of major national parties normally do.

Rather than chartering a plane for the entire campaign – as the Liberals and Conservatives will, and as the New Democrats have done in the past – Mr. Singh’s NDP will rent one hourly, here and there. Instead of jetting to different corners of Canada each day, he will spend extended periods busing around battleground areas, including the better part of a week in Ontario to begin the campaign.

Members of Mr. Singh’s campaign team will occasionally spin that approach as a sustainable one, with fewer carbon emissions.

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But it is less environmental choice than financial necessity – one reflection, among many, of the unusually rough shape in which the NDP enters this race and how it’s trying to adapt.

That adaptation, for all the grimness the NDP has endured since being on the brink of winning government in 2015, may be going a little better than outsiders would think amid poll numbers stuck in the low-to-mid teens.

NDP unveil new slogan, campaign ad ahead of federal election

Recent conversations with more than a dozen high-level New Democrats, including current and former campaign operatives and caucus members, highlighted causes for optimism that after a poor start to his leadership, Mr. Singh has been doing what he can to put his party in position to compete.

But another take-away from those conversations is that Mr. Singh’s improvement may have started too late. New Democrats are now left to hope that an untested leader running an unorthodox campaign is able to exceed low public expectations − if not to see the party emerge with more than its current 40 seats, then to ward off electoral disaster that could leave it unable to run party operations even at their current level.

In retrospect, it’s apparent that Mr. Singh was ill-prepared for what he was walking into two years ago − underestimating the depth of the NDP’s organizational problems, and overestimating how momentum from his leadership victory would carry over.

The first probably wasn’t his fault. “I don’t think the party was honest with itself, and therefore with Jagmeet, as to how bad things were when he took over,” says veteran MP Nathan Cullen, one of 11 current caucus members not seeking re-election.

The decision by the NDP caucus to keep Tom Mulcair as leader through a protracted contest to replace him, after party members voted him out at a 2016 convention, proved disastrous. Under a leader halfway out the door, the NDP’s infrastructure rapidly eroded; contact with supporters, including donors, was virtually non-existent.

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The other miscalculation was more on Mr. Singh, in that running a national party required a big step up organizationally after merely winning leadership. That campaign was relatively small scale − 35,000 votes for a first-ballot victory, less than $1-million in contributions to dominate the field in fundraising. His highest political position had been as a third-party Ontario MPP. But he arrived in Ottawa expecting that, without much adjustment, he could refashion the NDP into a younger, cooler, more diverse party. He displayed limited interest in institutional knowledge and surrounded himself with a team that had little federal experience.

It was publicly evident from Day 1 that it was a tougher adaptation than expected, as he frequently appeared unready for media appearances. But struggles behind the scenes may have been worse. Mr. Singh failed to grasp the need for outreach to a caucus that barely knew him; as he spent time away from Ottawa, where he lacked a seat in Parliament, MPs openly second-guessed him. As overwhelmed staffers tried to find their way around the capital, there was confusion around policy and communications decisions, and slow movement toward kicking party operations back into gear.

By last fall, with caucus mutiny a real prospect, Mr. Singh recognized the need for a reset. And New Democrats generally point to three developments since then that have offered a glimmer of hope.

One was a shakeup of top staff to bring in experienced hands. A pair of political veterans from Manitoba, where the NDP has a history of winning elections, are at the forefront: former provincial minister Jennifer Howard, as chief of staff and campaign director, and strategist Michael Balagus as interim chief of staff, before Ms. Howard took over, and now as an adviser.

“As MPs in caucus, we could feel the difference,” says Alexandre Boulerice, the NDP’s deputy leader and Quebec lieutenant. “Okay, somebody’s in charge there.”

A second morale booster was Mr. Singh’s February by-election win in British Columbia. Colleagues think finally entering Parliament and performing competently there restored some of the self-confidence that was Mr. Singh’s calling card during the leadership campaign, but waned as he was torn to shreds by critics.

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A third is the party’s election platform. Released this spring, it aims for an anticorporate, stand-up-for-the-little-guy vibe, hinging on hiking taxes for the rich to pay for expanded social programs (especially around health care) and populist measures such as capping cellphone and internet bills. Shifting back leftward after the past election’s failed attempt to win government through centrist pragmatism, it at least seems to be playing well within the party. Candidates and others say the early release gave local campaigns something positive to talk about and energized volunteers.

But the NDP’s problems run deep enough that they weren’t all fixable within a year of the October election.

The fact that more than half the country’s 338 ridings lacked a nominated NDP candidate, as of late last week, is currently the most obvious symptom. Recruitment was never going to be easy for a party with limited infrastructure and little shot at government, and Mr. Singh’s wheel-spinning during his first year left little runway.

Ms. Howard points to several factors that have made it difficult to quickly make up ground on nominations. Among them are process-oriented rules that make it more difficult to expedite nominations than in other parties, emphasis on attracting a diverse and gender-balanced slate, and − perhaps most tellingly − modern vetting requirements. In the digital era, all parties spend ample time scrutinizing old social-media posts and other footprints before green-lighting candidates. But the NDP winds up with more backlog, because of fewer staff to do the research.

That points to what underlies so many of the NDP’s challenges: lack of money.

On fundraising, Mr. Singh was again slow to move. His efforts have improved this year, including a return to the “Jagmeet-and-greets” he did during the leadership campaign. (Rather than selling tickets for events, this model involves free entry and then passing the hat.) But the party still reported only $1.4-million in donations in 2019’s second quarter, roughly even with the Green Party and only a fraction of the Conservatives’ $8.5-million and the Liberals’ $5-million.

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While citing the virtual halting of fundraising after the 2015 election, party officials suggest that the period before that election − when the NDP raked in cash at about three times its current rate − was an anomaly resulting from being close to government. The current totals aren’t far off from what it raised during Jack Layton’s era. But unlike then, parties no longer receive per-vote public subsidies (which Stephen Harper’s government scrapped). Nor can the NDP collect union donations, as under earlier leaders, which the per-vote subsidy compensated for after those donations were banned.

So the NDP, still millions of dollars in debt from the past election, is having to borrow against the building that it owns in Ottawa to fund this year’s campaign. Even so, NDP insiders tend to peg party spending during the coming writ period at around $10-million to $12-million − likely less than half that of the Tories and Liberals.

The belt-tightening will extend to every aspect of the campaign. Advertising will be modest compared with that of other parties. A party official estimated that the central campaign will have 50 or 60 staff members, down from more than 100 in 2015. Less will be spent on the ground to help local campaigns mobilize supporters.

Spending will disproportionately be in regions where the NDP already holds seats and is trying to protect them, along with a few ridings mostly around Toronto and Vancouver it is targeting for pickups, with limited presence elsewhere. Leaving many local campaigns to fend more for themselves increases the risk of them going rogue, including by distancing themselves from Mr. Singh, but that is a risk the NDP has to take.

One place it is not being completely bloody-minded about resources is Quebec. While elsewhere the party is at least competitive in ridings it currently holds, it faces a very uphill battle in many of its current 14 Quebec seats. But party officials are adamant that they won’t abandon the remarkable Quebec breakthrough of Mr. Layton’s final campaign

Backroom veteran Raymond Guardia, who ran Quebec efforts in the 2011 election, has been placed back in charge, with a model used under Mr. Layton in which the NDP’s Quebec campaign is a separate operation from the central one. According to Mr. Boulerice, Mr. Guardia “already negotiated the resources” for that wing, and while there might be less money than in previous campaigns, it’s unlikely to get cut further.

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This week, the NDP will launch an ad aimed at confronting head-on suspicions of Mr. Singh’s Sikh faith − including his wearing of a turban that would disqualify him from public-service jobs under Quebec’s new legislation − widely linked to dismal polling numbers in the province. According to a source familiar with the French-language spot, it will, among other things, encourage Quebeckers to link the way Mr. Singh looks “different” and their own cultural differences within Canada.

It’s the sort of attention-grabbing effort that the NDP is hoping will allow it to get bang for its buck, in some cases not paying for placement at all. Even by modern standards, there is much emphasis on Mr. Singh generating moments widely shared on social media. His officials talk about him being great at interacting directly with voters, and digital director Nader Mohamed − a holdover from the leadership, when Mr. Singh had some success on this front − will be alongside him on tour, trying to capture video that reaches a broader audience.

And in a faint echo of the Liberals with Justin Trudeau in 2015, New Democrats will count on Mr. Singh to use the leaders’ debates to surprise voters who have already written him off.

“There was a very high expectation coming out of the leadership race, and now I think Jagmeet will have the opportunity to beat expectations,” says Mr. Cullen, among those who see recent improvement. “I don’t think it was planned, but it is what it is.”

If expectations have lessened, pressure has only grown.

Borrowing against its building to fund its campaign is a fallback − put in place when the party bought the real estate under Mr. Layton during the vote-subsidy days − that the NDP can probably only use once.

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If nothing else, Mr. Singh and the team around him need to make the most of their limited resources, to give their party another chance at the rebuild it should have started sooner.