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Olivia Chow has been a front runner before, what’s different for the mayoral hopeful?

WATCH: Candidate Olivia Chow speaks with Global News with just days before Toronto votes for new mayor – Jun 22, 2023

TORONTO — Before the last high-profile debate of Toronto’s mayoral byelection campaign, Olivia Chow was prepared for attacks from the other candidates on stage. She was leading the polls, and in the crosshairs of her political rivals.

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What she was not prepared for was the large heart-shaped red card her campaign staff gifted to her the day of the debate. Her team’s signatures encircled a reminder to “be the heart,” to stay true to herself.

It’s a message that eluded Chow at times during her unsuccessful 2014 campaign for mayor, when she fell from an early front-runner position to a distant third. Her speeches at the time, she said, were often written by someone else. Her team included political operatives who shared a desire to win, but not necessarily her values. She questioned her English and herself.

“I never thought that I would run again,” she said in an interview.

As she returns to the political limelight, the biggest difference between her campaigns, now and then, is the trust in her own political vision, she said.

“I feel very much myself. I have a wonderful team that are very supportive. We work as a team, we strategize together,” she said.

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Chow has long been a standard-bearer of Toronto’s progressive left, rising from school board trustee in 1985, through to a 12-year stint on city council and eventually landing as a New Democrat parliamentarian in the House of Commons alongside her late husband and former federal NDP leader Jack Layton.

The 66-year-old supported an anti-homophobia curriculum in the 1980s, helped bring nutrition programs to Toronto schools in the ’90s, and fought back against exploitative immigration consultants in the 2000s. For much of the last decade, she founded and ran an organization to train community organizers.

Her campaign is headlined by a pledge to get the city back into social housing development and an annual $100-million investment in a program to purchase affordable homes and transfer them to non-profits and land trusts, part of a larger pledge to crack down on so-called renovictions.

She wants to expand rent supplements to 1,000 homes and boost the number of 24-7 respite homeless shelters, promises funded by an expanded land transfer tax on homes purchased for $3 million and above.

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Her critics argue there are candidates better positioned to take on the city’s challenges.

Chow has not delivered a fully costed platform and will not say how high she would raise property taxes, though she says any increase would be modest. Her campaign has faced questions about whether she is well-placed to negotiate financial support for Toronto’s nearly $1-billion budget shortfall, especially with a premier openly hostile to her campaign.

“If Olivia Chow gets in, it’ll be an unmitigated disaster,” Ontario Premier Doug Ford told reporters Wednesday. Ford has backed ex-police chief and failed Progressive Conservative candidate Mark Saunders but said he would work with Chow if she’s elected.

A win for Chow in Monday’s byelection would mark a high point in her decades-long participation in Toronto politics. But Chow also sees her potential mayoralty as an opportunity to renew leadership.

“Bringing in people that are younger, have a different perspective, that are more open for democratic engagement,” she said.

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“It excites me almost as much as being able to start building again, because you can set up a structure at city hall that can outlast your term.”

Following her 2014 loss, Chow called one of her mentors, Marshall Ganz, a longtime organizer with the United Farm Workers credited for helping shape Barack Obama’s field operations during his 2008 U.S. presidential run. Chow took Ganz’s political leadership course at Harvard University and returned with the curriculum that inspired the Institute for Change Leaders, the organization she founded in 2016.

Supporters say the organization’s work could help shape her term as mayor.

“What her work … demonstrates to me is that she is someone who demonstrates leadership and cultivates leadership,” said Coun. Ausma Malik, who was a student activist, labour organizer and school board trustee before she was elected in October to represent Spadina-Fort York.

“That is what we need to meet the urgent needs of our city. To make sure that we are stepping up with the resources, the collaboration, the advocacy that the head of the largest city in Canada must have.”

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For all the talk of her record, pollsters offer another explanation for Chow’s lead in the polls.

“She is way better known. And to a large extent, a lot of this is just name recognition, it being municipal politics and with no party ID,” said Lorne Bozinoff, president of Forum Research, a prominent Toronto polling firm.

She has the “left lane” largely to herself, Bozinoff said, tapping into the NDP’s organizational strength in a byelection dominated by candidates with closer ties to Liberal and Conservative political machines.

With Chow’s support polling in the range of 30 per cent among decided voters, double her next closest rival in the crowded field, “this is her election to lose,” he said.

When former mayor John Tory admitted to an affair with a staffer and resigned in February, triggering the June 26 byelection, Chow first encouraged her stepson and former city councillor Mike Layton to run. Layton had, however, just months earlier opted not to seek re-election to council in order to spend more time with his young family. When former progressive councillor Joe Cressy also declined a run, Chow started seriously considering one.

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“It was a sense of responsibility. Someone needs to do this. I have the experience. I don’t have a young family. I can handle it,” she said.

She has referred to this campaign as akin to her third run for mayor, accounting for her late husband’s unsuccessful 1991 campaign. When the couple married in 1988, they set out a list of priorities they hoped to tackle in their political partnership.

It became a road map of sorts, she said. From the environment to homelessness, some of the issues they charted have only become more urgent since then.

“That is unfinished work,” she said.

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