The increasing political discontent in the liberal stronghold may lead to a notable advance for the conservatives in the Ontario by-elections, which could put Prime Minister Justin Trudeau's leadership to the test. On Monday, voters in the Toronto St. Paul riding will head to the polls to elect a new member of parliament.

Caroline Bennett previously held the federal seat before stepping down last year, and the seat has remained heavily liberal for over three decades. However, with the Grets family's popularity plummeting to record lows, some now see the local race as a referendum on the Prime Minister.

With no current candidate, the pressure is on the liberal candidate Leslie Church to maintain the red color. However, she will need to combat a rising competitor and a divided electorate, as well as the potential for confusion at the polls to secure a win.

The housing and homelessness crisis

Last Wednesday, five days before the by-election on June 24, CTV News interviewed Church in her campaign office in downtown Toronto. Red signs bearing her name were plastered on the back wall, while two volunteers sat at a table facing the glass storefront. Four boxes of day-old pink and chocolate donuts sat untouched on another table beneath a riding map.

Just before the interview began, a homeless man entered the campaign office seeking relief from the heat, and one of the staff offered him water. The scene embodies the issues plaguing Toronto St. Paul.

When asked to explain what her goal is in facing the desire for change in the riding, Church responded, "People are exhausted right now. The primary concern I hear is around housing and rent costs; 60 percent of our families here are renters."

"Change doesn't mean throwing out the baby with the bathwater. Change doesn't mean abandoning your values; change means 'let's do things better.'

Retreat strategy

Church, who was Chief of Staff to Finance Minister Chrystia Freeland, is trying to overcome her competitor with a strategy that links her to a dated regional leader.

Church stated, "People are worried about the alternative here that promises cuts, which resembles a Mike Harris style that a lot of people in St. Paul already remember," linking her conservative opponent to an Ontario Premier who came to power in the mid-1990s.

"The decade of the Harris government was one where, you know, our teachers, our nurses, our paramedics, our public services, you know, were all disrupted. And that's not what they want to go back to."

Domestic and international political struggles

Apart from concerns around housing and affordability, data scientist and pollster Nick Nanos says the by-elections could also hinge on "the hot issue of what’s happening in the Middle East between Israel and Hamas."

Eleven percent of voters in Toronto St. Paul are Jewish.

The office of conservative candidate Don Stewart is located across the street from the church headquarters. He took a leave from his job at the Canadian Investment Organizing Agency, which regulates investment companies and mutual funds to run for office. Stewart did not respond to multiple interview requests from CTV News via email, social media, and phone calls.

However, it seems he is tailoring his message to resonate with Jewish voters. Among three videos on his Facebook page, one echoes familiar remarks from Pierre Poilievre, stating that "After eight years of Justin Trudeau's rule, crime, chaos, and disorder are rampant in our streets," and that there is a "notable increase in antisemitism and incitement to violence, near schools and synagogues."

There are signs in residential streets near the Jewish community center in Forest Hill indicating that Stewart's message is resonating. Three houses on a street near the synagogue have placed conservative signs in their yards. Two of the homeowners stated that this is the first time they publicly announced their intent to vote. They have been long-time liberal supporters and wanted to signal that they have changed their positions.

The NDP appeals to hearts and minds

During the 2021 federal election, the NDP came in third in Toronto St. Paul. Nanos states he will analyze the data to determine whether leftist voters strategically cast ballots.

"Will they hold their noses and vote liberal to ensure liberals hold on, or will they stick with Jagmeet Singh and the New Democrats to send a message to Justin Trudeau?"

As Amrit Bahar paints murals in residential buildings, the NDP candidate says she hears a strong desire for political change when she knocks on doors. In the final days of the race, the community organization is ramping up its ground game with an emotional appeal to deter potential supporters from backing the liberals to prevent the conservatives from winning.

Bahar said, "Don't act out of fear, don't fall into that, I'll go and vote this way because I'm afraid of the conservatives... Vote according to your values and vote for a party that will truly uphold your values," "what is here in your heart."

Longer ballot reform

The interest in the race in Toronto St. Paul has become more intriguing due to the record number of candidates running in the by-election. The ballot includes the names of 84 registered candidates, 76 of whom belong to a protest movement.

Glen MacDonald is one of the independent candidates for the "longer ballot committee" that is pushing for electoral reform. He voted in the advance polls and found his name in the middle of the one-meter long ballot.

MacDonald states that the goal of protesting for the longer ballot initiative is to force people to see the need for electoral reform.

"It's more about getting people to think about what they do when they vote and really ask themselves: Is my vote important?"

Statistics from Elections Canada show that in the 2021 federal election, the conservatives received 200,000 more votes than the liberals but ended up with 41 fewer seats.

MacDonald, who advocates for proportional representation, said, "How is that fair? The (majority) voting system distorts the results and discourages people from voting."

However, the large number of candidates could lead to divided votes, potentially creating more fractures in the liberal stronghold and raising further questions about Prime Minister Trudeau's ability to lead his party to victory in the upcoming general elections.