The streets of Toronto’s Forest Hill neighbourhood are lined with arching maple trees and multimillion-dollar homes, a plummy refuge for some of Canada’s wealthiest families and top business leaders. Now it’s also a red-hot political battleground in the fight to control the country’s highest office. 

On Monday, residents of this part of Toronto will vote in a closely watched special election for a vacant seat in the House of Commons. For Prime Minister Justin Trudeau, who has held power since 2015 by consistently winning big in Canada’s largest city, the stakes are high. A loss would dramatically raise the pressure on the embattled leader to quit ahead of a national election expected next year. 

Trudeau is facing a crisis of confidence in his ninth year in office. Polling shows he’s fallen out of favour while his main opposition, the Conservative Party, is surging. That puts unexpected seats in play, including this one, known as Toronto-St. Paul’s. Voters here have chosen the Liberal Party in every election since 1993, but pollsters say the Tories are within striking distance this time.

It’s a battle, in miniature, over the fault lines and forces that have stirred unrest across the country. Canada’s economy is growing at a sluggish pace. Housing is unaffordable to many, and elevated interest rates are still frustrating borrowers and aspiring homebuyers. 

The Israel-Hamas war looms especially large in Toronto-St. Paul’s, where Jewish residents comprise about 11 per cent of the population. Like U.S. President Joe Biden’s Democrats, Trudeau’s big-tent Liberals are trying to preserve support from both Jewish and Muslim communities while navigating a strained relationship with Benjamin Netanyahu’s government. 

The delicate approach has made Trudeau vulnerable to attacks from every direction. In the months since Oct. 7, the Conservatives have accused the Liberals of being too soft in supporting Israel and failing to combat antisemitism at home. This week, after Canada listed Iran’s Islamic Revolutionary Guard Corps as a terrorist entity, Conservative Leader Pierre Poilievre said the government was only making the announcement now to boost its chances in Toronto-St. Paul’s. 

Don Stewart, the Conservative candidate, has distributed fliers with messages condemning Hamas and supporting Israel’s right to defend itself. 

In a debate this week, Liberal hopeful Leslie Church — who was Finance Minister Chrystia Freeland’s chief of staff — promised to crack down on hate-motivated crimes targeting Jewish residents in part by calling for an increased police presence in the city. 

“We stand for fighting the wave of antisemitism we’ve seen in our communities,” she said.

A victory in Toronto would be a coup for the Conservatives, which hold no seats within the city of Toronto itself, though they do have representation in the suburbs. It may cement Poilievre’s status as the front-runner, and signal that he has a broad path to victory next year.

Jeff and Betty Kane, Forest Hill residents who voted for Trudeau when he first entered office, said they intend to vote for the Conservatives in the byelection, even though they’re skeptical of Poilievre’s leadership.

“We’re not for Poilievre so much as we’re against the Liberals,” said Jeff Kane, 78, a retired engineer. “I’m not actually sure I’d support him, were it not for how badly we’re doing as a country with Trudeau. We’re not growing economically as we should be.”

Trudeau’s approach to the Middle East is a “total mess,” he added. “For a while he was flip-flopping on Israel — for them, against them, and for them again. Now, after about eight months since the Hamas attack, he’s totally against Israel.”

Until now, despite his dreadful polling numbers, Trudeau has avoided calls for his resignation from within his party’s caucus. But if it loses a Liberal stronghold in left-leaning Toronto, there’s a risk that private grumblings will break into the open and imperil the leader’s grip on power.

At the same time, some Liberal insiders, speaking on condition they not be identified, doubted a loss would be enough to push Trudeau out. Byelections typically have weak voter turnout and can be influenced by events that have no bearing on a general election result, they argued.

The area’s reputation as a Liberal bastion is partly owed to its former representative, Carolyn Bennett, a party stalwart who stepped aside to become Canada’s ambassador to Denmark. Her support ran deep in middle-class neighborhoods like Wychwood and Humewood, while affluent Forest Hill tended to lean right.  

The results come down to “whoever’s most motivated to vote,” said Dan Arnold, chief strategy officer at Pollara and a former Liberal pollster. The Conservatives are on the rise across Canada, but the Liberals are better at campaigning in progressive Toronto districts, he said. 

“If the Liberals lose this riding, it’ll definitely get people talking,” said Arnold.