Forget Trudeau. Jagmeet Singh’s leadership might be questioned next.

It's Mr. Singh that the upcoming byelections might force to finally take a political walk in the snow.

Since calling two by-elections to be held in September, there has been a lot of speculation about what losses in these seats would mean for Canadian Prime Minister Justin Trudeau's viability as Liberal Party leader.  

However, what more folks should be looking at is what these two by-elections could mean for Mr. Trudeau's Parliamentary dance partner, New Democratic Party Leader Jagmeet Singh.

With seven years under his belt as party leader, the reality is that Singh has made few political gains during his extended time at the wheel. He’s now lost two general elections, placing fourth in both and well behind the high watermark of support enjoyed in 2011 by the late Jack Layton. Nor do his prospects for the next election look much brighter. The federal Liberals have shed as much as 20 points of support, but to date, Singh has not found a way to bring those disenchanted Liberal voters into his far-left wing party’s fold. Case in point - in the recent Toronto St. Paul’s by-election, the NDP lost a considerable amount of vote share, even though the NDP holds the riding at the provincial level. For the most part, those voters seem to be migrating to the Pierre Poilievre-led Conservative Party, whose focused messaging on lowering taxes, building homes, and reducing crime rates has resonated amid Canada's cost of living crisis and have offered a clear alternative to Mr. Trudeau's government. 

Singh, on the other hand, has struggled to find a lane. This problem can and should be attributed to Mr. Singh's cozy relationship with the Trudeau Liberals. For those who don't regularly follow Canadian politics, the governing Liberals do not have an outright majority of seats in Canada's Parliament, which means they need another party to vote with them to prevent the government from falling. Mr. Singh and his caucus have helped the Liberals in this fashion for years, entering into a formal agreement to prop the Liberals up until 2025. 

However, as much as NDP backroomers might think that this deal has allowed the party to get its policy priorities considered by the federal government, there's little evidence to suggest that the Canadian public appreciates the effort. The opposite may be true. Polling data suggests the NDP's enthusiastic support for all things Liberal, including things like the highly unpopular carbon tax and hard drug decriminalization, has blurred their party’s brand with that of the Liberals’. It’s also making the NDP increasingly irrelevant to an electorate hungry for change from the passé brand of woke, hard-socialist progressivism that seems to be turning off young voters en masse.

So unpopular are some of these policies that Singh’s provincial party cousins in Alberta are looking to formally divorce themselves from the federal party mothership. And they’ve created jurisdictional issues in places that the NDP can ill afford to lose support if they want to grow their seat count. For example, the government of Quebec has staunchly opposed some of the NDP's signature policies that they’ve forced the Liberals to implement.

But instead of trying to fix this brand differentiation problem, Singh has leaned into it. He’s allowed his House leadership team to stray far beyond the confines of the confidence agreement with the Liberals. In so doing, the caucus frequently appears as ineffectual opposition to Canada’s wobbly governing party, having let them off the hook for issues for which they should have been held to account. Singh's continued support for problematic Speaker Greg Fergus springs to mind as one example, with the NDP’s repeated assistance in shutting down debate on controversial Liberal legislation via procedural motions being another. When the work of Parliamentary committees are considered, there are many more.

Part of this may be due to the fact that Singh literally can’t afford to topple the government and go to an election. Under his leadership, the NDP's fundraising numbers have been lacklustre, and their war chest remains shallow. This state of affairs speaks both to Singh’s inability to find policy ground that will expand his donor base, and to effectively communicate to the public. He has never been accused of being a skilled orator or a policy heavyweight in debate, and his digital presence has consistently peaked on a scale somewhere between non-existent and vaguely cringe. That he’s allowed Mr. Trudeau’s Liberals to largely take credit for (albeit disastrous) policies his caucus has pushed through via their confidence agreement without any sort of substantive challenge is mind blowing.

None of this bodes well for Singh given that Conservative Party leader Pierre Poilievre recently launched a barrage of ads against him, arguing that he is an opportunist who is only propping up the Liberals to become eligible to vest his pension in 2025. Mr. Poilievre also held a massive rally in Winnipeg over the weekend, calling the by-election there a "mini carbon tax referendum" while referencing Singh's longtime support of this Liberal's controversial policy. Both of these are powerful messages that will resonate with many voters who are frustrated with the rising cost of living and see Mr. Singh's NDP as complicit in passing Liberal policies that helped cause the problem. Given his lack of funds, policy, communication skills and now-inextricable association with Mr. Trudeau, Singh doesn’t have any easy high ground to climb upon to fight either point.

And he can’t easily backstop his weakness from his caucus ranks, either. Mr. Singh's already small team of Members of Parliament is losing some of its highest-profile members in the next election. Veteran MPs Charlie Angus, Randall Garrison, Carol Hughes, and Rachel Blainey have all announced that they will not reoffer in the next election. Their news follows the departure of fellow veteran MP Daniel Blaikie, whose resignation precipitated the current Winnipeg area by-election. No matter how Singh slices it, the collective departures of these MPs will be a loss of firepower and heft going into the next campaign that he can ill afford given his personal policy and communication weaknesses. It will be hard for him to replace them, and harder still to find skilled candidates willing to take a leap of faith on his leadership.

And it's in that context that Mr. Singh now takes his party into two more by-elections, but this time with higher stakes. The NDP has held the Winnipeg riding of Elmwood-Transcona for the better part of the last several decades, so a loss in that seat now would be a stunning rejection of Mr. Singh by the sizeable constituency of working-class people that live there. And the NDP has also been heavily pumping the tires of their candidate in the Montreal-area by-election. Mr. Singh's candidate there is a well-known local city councilor who was credited in part for the NDP's 2011 electoral breakthrough in Quebec and was recently quoted as saying the party is in a position to win the race. Having set expectations high, anything short of a win here would also be a blow to Mr. Singh's future viability as party leader and, at a minimum, should force the NDP to rethink their willingness to support Mr. Trudeau's government in the future.

So, come election day for these by-elections, all eyes this fall should be on Mr. Singh's future as NDP leader as much as they are on Mr. Trudeau.

That's because unlike Mr. Singh, win or lose these by-elections, Mr. Trudeau's leadership prospects are ultimately in his own hands. The Liberal Party does not have a mechanism to pry a leader loose between elections. And unlike the recent case of American President Joe Biden's ouster from his country's upcoming presidential ballot, the Liberals do not have an obvious successor to Mr. Trudeau waiting in the wings, nor a political force de la nature like American Speaker Emerita Nancy Pelosi to bring the sword down upon him. At this point, that means that Mr. Trudeau will only leave on his volition or after defeat in a general election.

Neither of these things are true for the Mr. Singh. There are many charismatic, high profile up and coming progressives that could easily fill his shoes, and his party’s constitution contains mechanisms that could easily be used to punt him. There are also many long time NDP activists who have already proven willing to publicly grumble about the lack of perceived benefit from Singh’s deal with the Liberals.

So, if Mr. Singh keeps enabling Mr. Trudeau with nothing to show for it but a pension and angry prospective voters, it might be he who is first forced to take a walk in the snow by his party, not Mr. Trudeau.