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Campaign signs line a residential street in the Toronto-St Paul federal riding on June 21.Sammy Kogan/The Globe and Mail

Liberals have held the riding of Toronto-St. Paul’s for three decades, but heading into Monday’s federal by-election, people in the party say that while they expect to win, it will be a closer race than it should be.

With national polls showing the governing Liberals badly trailing the Conservatives and issues such as affordability, Israel’s war with Hamas, and the recent capital-gains tax hike having a pronounced impact on the riding, the race has turned from a typical Liberal cakewalk to an all-hands-on-deck push to the finish.

The Globe and Mail spoke with 20 Liberal, Conservative and NDP insiders for this story. They ranged from MPs to staffers to party organizers and loyalists. All of them had direct insights on the mood in their camps and the campaigns on the ground.

They described a Liberal team in the midtown riding feeling the pressure, a buoyed (but realistic) Conservative campaign, and a low-expectations New Democratic effort.

The Globe is not identifying most of the people interviewed because they were not permitted to publicly discuss campaign data or strategy.

Early in the race, Liberal nerves were frayed as internal data showed the Conservatives were so close that three Liberals said the result was a toss up. But with a steady stream of federal cabinet ministers, MPs and Parliament Hill staffers descending on the usually safe seat to door-knock and work the phones, Liberals are entering the final stretch confident in a win on Monday.

The riding’s importance to the party is underscored by the 2011 general election. Even during the Liberals’ worst ever result, they held onto that seat. In the most recent federal campaign, long-time MP Carolyn Bennett, who resigned her seat late last year, won with a 24-point margin.

The reason why a win matters now is less about numbers in a minority Parliament, and more because of what a loss would say about Liberal prospects in every other riding in Canada.

“If Liberals can’t win St. Paul’s, it’s difficult to understand how there’s a path back to government through the next election,” said Dan Moulton, a Liberal strategist and partner at Crestview Strategy.

While he and most others are banking on a win, the high stakes were felt on Parliament Hill this month. Two Liberal staffers say the race is viewed as a test of Mr. Trudeau, who has been adamant that he will stay on as leader despite the bad polling and insufficient fundraising. However, that sentiment was played down by others, although they acknowledged it’s a must-win riding.

Carrying the banner for the Liberals is Leslie Church. As Finance Minister Chrystia Freeland’s former chief of staff, she has deep roots in the party but is relatively unknown in the riding. Ms. Church began campaigning for the nomination last fall but the Liberals delayed a vote as they searched for someone with better name recognition.

Among those courted by the party was the area’s city councillor, Josh Matlow, who three sources said was heavily lobbied by top Liberals. He declined but has endorsed Ms. Church and campaigned with her in the area.

The riding is known for its affluent neighbourhoods, but those pockets are surrounded by thoroughfares lined with small businesses, apartment buildings and condos. Statistics Canada data shows that about two-thirds of the households in the riding are renters.

In the upscale Forest Hill neighbourhood, signs for Conservative Don Stewart littered the lawns of large, stately homes. But there were few signs of the election campaign on the major streets nearby and the Liberals have the upper hand in the sign game in other neighbourhoods.

Already, 10,787 people voted in advance polls, in what is an unusually crowded ballot of 84 candidates.

Voters who spoke to The Globe reflected a broad mix of opinions. Some said they still supported the Liberals out of tradition or because of programs such as $10/day child care. But they also questioned Mr. Trudeau’s decision to stay at the helm. Others were dissatisfied with the Prime Minister’s handling of the war in Gaza and still others said they were also unsure about Conservative Leader Pierre Poilievre, whose positions on key programs such as child care and climate change remain unknown.

In an interview, Ms. Church said she isn’t feeling pressure, but does feel a “responsibility.” She said she is hearing broad frustration with governments at all levels, as people are stretched by the affordability crisis and as cracks appear in essential services such as housing, health care and education.

“Governments at all levels need to get back to basics,” Ms. Church said.

Unlike the staunchly progressive brand that Mr. Trudeau carries, Ms. Church said she is pitching herself to voters as a “strong, centrist choice.”

Prior to Ms. Bennett’s tenure, the riding used to swing between Conservatives and Liberals. Despite that, Tories tend to agree that it’s unlikely Mr. Stewart, who did not agree to an interview, will win. Still, Conservatives believe a close race in a Liberal stronghold will spell success in other nearby ridings in the Greater Toronto Area.

“If they can close the gap in a safe riding, what about those ones that are kind of wobbly?” said Conservative strategist Shakir Chambers, a principal at Earnscliffe Strategies.

Several Conservatives also said there’s a debate within the party about whether they even want to win the race, for fear that such a result would lead to Mr. Trudeau’s resignation and more unknowns in a general election.

Despite the area going New Democratic in the past two provincial elections, the party hasn’t put significant resources into the riding and the local campaign has largely flown below the radar. However, it did receive an endorsement from former councillor Joe Mihevc.

NDP candidate Amrit Parhar, a community organizer and non-profit director, told The Globe that the affordability crisis and frustration with the governing Liberals are the main issues raised by voters. “It’s coming to the point where folks can’t really live in the city any more,” she said.

Ms. Parhar said she has heard some criticism of the NDP for propping up the minority Liberals, but mostly questions about when the deal will end.

“I feel like we’re probably going to break out soon. And I think that will be the right decision,” she said.

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