Could Conservatives beat Liberals in Toronto byelection?

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Byelections don’t matter until they do and Monday’s race in Toronto–St. Paul’s matters, which is shocking. The contest to replace Carolyn Bennett, who has held the riding since 1997, should be an easy win for the Liberals.

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That Toronto–St. Paul’s is in play, that Liberals are nervous and that there is chatter of them losing tells you things are bad for the Liberals. Cabinet ministers have flooded the riding, young staffers have been shuttled in from Ottawa to knock on doors of residents for the fifth or sixth time asking for them to vote for Leslie Church.

Church should win in Toronto-St. Paul’s.

She’s someone with extensive government and private-sector experience, including a stint at a major law firm and three years working at Google’s Canadian headquarters. She spent the last eight years working as the chief of staff to various ministers, including three years as chief to Finance Minister Chrystia Freeland.

That kind of resume and Church’s party connections would normally be enough for her to cruise to victory, but these aren’t normal times. The Trudeau Liberal brand has lost its shine, the party is polling badly, there are a lot of small business owners and professionals in the riding who are upset at the capital gains tax changes and there is the significant Jewish population upset at the government’s reaction to the terror attacks launched by Hamas on Oct. 7, 2023.

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If this election were held just in the neighbourhood of Forest Hill, where much of the Jewish community is located, the Conservatives would win in a landslide. The riding is much more than Forest Hill, though, as it’s large and diverse in terms of income ranges, housing styles, ethnicity, religion and more.

While Church should win this byelection, that’s not a given at this point.

The NDP will do well in much of the western part of the riding where signs, demographics and history show that the party has support. The Dippers hold this riding provincially, but candidate Amir Parhar is facing an uphill battle given that the NDP normally underperforms the party’s national polling support in St. Paul’s.

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Don Stewart is hoping to do better than the Conservatives normally do, but the party is managing expectations.

“We’re not winning. Closer than normal, but not winning,” one senior Conservative said via text.

Of course, speak to Liberals campaigning on the ground in Toronto–St. Paul’s and they will tell you they aren’t winning. The reaction from many voters at the door has not been friendly and even those sympathetic to Church aren’t fond of Prime Minister Justin Trudeau.

For Stewart to win this riding for the Conservatives on Monday, he needs to convince disaffected Liberals to switch their vote to him or simply stay home and not vote. It’s that last part — Liberals staying home — that has the party worried the most.

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If voters are so turned off by Trudeau, by the government’s stance on Israel and the capital gains tax changes that they stay home, things could move in favour of the Conservatives.

Stewart has been hitting a message of stopping the crime, important in a riding where auto thefts have skyrocketed. He’s also pushing hard on inflation, affordability and Trudeau’s waffling support of Israel.

Church has been focused on issues like $10-a-day childcare, a renter bill of rights and affordability. Her signs emphasize her name with the Liberal brand a bit smaller and the Trudeau name smaller still.

For Church to win, she needs voters who are fed up with Trudeau but not the Liberal party to come out and vote for her in spite of the leader.

If the Liberals hold Toronto–St. Paul’s on Monday, even by the narrowest of margins, Trudeau will take the win as proof that the public still loves him and wants him to stay on. If he loses, the pressure for him to resign will be even greater.

Monday will be a very interesting evening for political watchers.

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