Upcoming federal byelections will put Singh and the NDP brand to the test

An upcoming byelection in Montreal is being seen as a challenge not only for Prime Minister Justin Trudeau’s leadership but also for NDP Leader Jagmeet Singh, as his party strives to hold onto one seat while attempting to wrest another from the Liberals.

On Tuesday, the NDP will hold a caucus meeting in Montreal, where discussions will likely focus on strategies for the next parliamentary session following the party’s recent decision to end its confidence-and-supply agreement with the Liberals.

This decision to withdraw from the agreement came just over a week before two byelections in Winnipeg and Montreal.

The Winnipeg riding of Elmwood–Transcona, traditionally an NDP stronghold, has been won by the party in 10 of the last 11 general elections since 1988.

Former NDP MP Françoise Boivin stated that if the party fails to retain Elmwood–Transcona, it could raise doubts about whether Singh should have ended the agreement with the Liberals sooner.

"It would be devastating, in my book. If they lose this [riding], it's going to be a hard, hard hit and very hard for Jagmeet to assert his leadership," Boivin told CBC News.

The Conservatives are making a concerted effort to claim the riding from the NDP, part of which involves linking Singh to the declining popularity of the Trudeau Liberals.

Conservative candidate Colin Reynolds has put up signs throughout the riding, showing photos of Singh and Trudeau together, labeling the NDP leader as “sellout Singh,” a jab at the party’s former partnership with the Liberals.

The NDP is without an incumbent in the race after Daniel Blaikie stepped down earlier this year to join Manitoba’s provincial NDP government. Blaikie, who had held the seat since 2015, comes from a family with deep roots in the riding. His father, Bill Blaikie, represented the area from 1988 to 2008.

Apart from the Blaikies, only two others have held the seat in the past 25 years: New Democrat Jim Maloway (2008–2011) and Conservative Lawrence Toet (2011–2015).

Andrew Thomson, a former federal NDP candidate and Saskatchewan’s former finance minister, remarked that with no Blaikie on the ballot, the byelection might become a referendum on Singh’s leadership.

"It's more of an open seat, but it's also a seat that the NDP needs to prove that they can not only hold but can win," Thomson told CBC News. "That is, I think, the test of leadership here, is that it's beyond Blaikie now. It is about the NDP brand and partly about Singh's leadership."

The Winnipeg byelection is scheduled for the same day as the one in Montreal’s LaSalle–Émard–Verdun riding.

The NDP is looking to take this Montreal seat from the Liberals, and Singh was recently campaigning in the area with NDP candidate Craig Sauvé, just days after announcing the end of the deal with the Liberals.

The seat has largely been held by the Liberals over the past century, with former prime minister Paul Martin among its representatives. Exceptions include the Progressive Conservative dominance in the 1980s and a brief period after the NDP’s Orange Wave in 2011.

Some polls indicate that LaSalle–Émard–Verdun could become a three-way race between the Liberals, NDP, and Bloc Québécois. However, the NDP has struggled to regain its 2011 momentum in Quebec, holding just one Quebec seat since Singh took over as leader.

Eric Grenier, a polling analyst with TheWrit.ca, noted that if the NDP were to win in Montreal, much of the credit might go to Sauvé rather than Singh.

"They have a candidate who has some local profile, and if there is going to be an anti-Liberal, anti-Trudeau movement, it could go to the NDP," he said. "[The riding] has a profile that is a little bit more friendly to the NDP than other parts of Montreal. So they do have an opportunity there. But if they do win the riding… a lot of the credit will go to their local candidate because the party is not doing particularly well in Quebec."

Boivin, who was elected in the NDP’s 2011 Quebec breakthrough, echoed this view, suggesting a victory in Montreal would be more attributable to Sauvé than Singh. Still, she believes the NDP is well-positioned for a good showing.

"I'm sure if they finish third, it's going to be a big disappointment because they have to be very close to the winner or win it themselves to feel that it bodes well for a general election," she said.

Singh told reporters in Toronto last week that he plans to continue leading the party regardless of the outcome of the byelections.

"I will be leading the party into the next election," he stated.

Thomson suggested that even if the party loses both byelections, Singh may still receive some leeway from party members, as the decision to end the agreement with the Liberals is still fresh.

"The change in the supply and confidence agreement, I think, is trying to reposition the NDP. We'll see whether that's successful, and I expect that the party will give him sufficient runway to move in that direction," he said.

Voters are set to head to the polls in both ridings on Monday.